sailboat tour key west

THE 10 BEST Key West Boat Tours

Boat tours in key west.

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4.0 of 5 bubbles & up
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Key West Historic Seaport
Mallory Square
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The ranking of tours, activities, and experiences available on Tripadvisor is determined by several factors including the revenue generated by Tripadvisor from these bookings, the frequency of user clicks, and the volume and quality of customer reviews. Occasionally, newly listed offerings may be prioritized and appear higher in the list. The specific placement of these new listings may vary.

1. Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres

2. Half-Day Cruise from Key West with Kayaking and Snorkeling

3. Key West Small-Group Sunset Sail with Wine

4. Florida Keys Reef Snorkel & Sail Adventure

5. Adults only Sunset Cruise from Key West with Champagne

6. Sunset Sail in Key West with Beverages Included

7. Key West Safari Eco Tour Adventure with Snorkeling

8. Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

9. Reef Snorkel & Sail Adventure from Key West

10. Key West 3hr Water Adventure with parasail, jet ski, banana boat

11. Key West Dolphin Sunset Sail with Wine and Tapas Pairings

12. Key West Snorkeling with Breakfast and Unlimited Mimosas

13. Sunset Sail Cruise in Key West

14. Sail, Snorkel, Kayak, Dolphins, and Lunch with Honest Eco

15. Sunset Sail on Historic Schooner in Key West

16. Shallow Water Snorkeling and Dolphin Watching in Key West

17. Key West Glass-Bottom Boat Tour with Sunset Option

18. Schooner Bloody Mary Day Sail

19. Key West Sunset Cruise with Live Music, Drinks and Appetizers

20. Key West Afternoon Sightseeing Sail on America 2.0 with 2 drinks

21. Key West Rum and Reef: Snorkel Adventure and Sunset Sail

22. Key West Dolphin & Snorkel Experience

23. Key West Afternoon Reef Snorkeling with Open Bar

24. Sunset Sip and Sail Key West with Open Bar and Live Music

25. Key West Schooner Backcountry Eco-Tour: Sail, Snorkel & Kayak

26. Key West Schooner Sunset Sail with Full Bar Included

27. Key West Private Charter Rental: Luxury Boat with Captain

28. Key West Full-Day Island T'ing Eco-Tour: Sail, Kayak and Snorkel

29. Schooner Key West Day and Sunset Cruises with Full Bar

30. 2-Hour Sunset Sail On Schooner When And If

What travelers are saying.

Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres
Key West Sunset Dinner Cruise with Tropical Buffet Dinner
Florida Keys Reef Snorkel & Sail Adventure
Key West Small-Group Sunset Sail with Wine
Half-Day Cruise from Key West with Kayaking and Snorkeling
Key West Extreme Adventures Shark Tours
Danger Charters
Schooner Jolly II Rover
Classic Harbor Line
Cruisin’ Tikis KeyWest
Breezin Sailing Charters
All In Fishing Charters
Wild About Dolphins
Laid Back Key West
Venus Charters

Private & Shared Sailing Charters

Sunset sail key west.

Have the sea to yourself with Sunset Sail Key West—chartered sailing trips led by us, tailored to you.

Get inspired with our most popular trips!

Private sunset sail.

Chillout Lilypad Sail

Key West Daysail

Sunset Sail on When & If

Privates Charters

Discover your perfect private charter.

Set out on a snorkeling, stargazing, or sunset sail, or build your own custom trip. Romance, relax or unwind from the privacy of your own chartered sailboat.

Shared Trips

Come together on a shared charter.

Rise above the crush of the crowds and set sail on a unique shared sunset charter, with a few friends you haven’t met yet. A personable local crew and captain will treat you to a stunning sunset view from the deck of an unforgettable vessel– General Patton’s elegant, private schooner When and If.

Three Classic Boats

View our fleet.

We sail a fleet of three vintage sailboats, each with their own unique charm and appeal. A custom sloop, a classic ketch, and a historic schooner are waiting to make memories with you on the crystal clear waters of Key West. Each boat is suited to different types of outings, so take a moment to get acquainted with our vessels.

Real. Fun. Sailing.

When And If is back at beautiful Stock Island Marina!

Check Out Our Ship's Store!

Wreckers' Race Season Is Back!

Hello, Sailor! Don’t miss out on the latest Sunset Sail news & offers.

Friends of SSKW

Legal & safety.

An Authentic Key West Sailing Experience!

Come sail Key West’s most photographed ship – the Jolly II Rover , a square-rigged topsail schooner! A Key West sailing adventure aboard the Schooner Jolly II Rover takes you back in time on a classic 80’ tall ship to an era of pirates, rum runners and privateers seeking freedom and solitude. Their spirit of independence lives on daily on the Jolly II Rover.

Roling Thunder Happy Hour from James Papagno on Vimeo .

The crew from Active Perspectives and Bombarda Rum chose the Rover to set the stage for their latest investment video. They were kind enough to create a short director’s cut for us to use. Cheers gents! (see the full video here )

Sunset Sail

A top Key West attraction is the Jolly II Rovers famous “Red Sails in the Sunset” 2 hour sunset sail! Take in a memorable sail of Key West’s most famous sights while the sun works its magic turning the sky brilliant colors. With our distinctive red sails and being the only square rigged tall ship in Key West, the Jolly II Rover is the focal point as we sail past the Mallory Square Sunset Celebration. Help raise the sails, fire the cannons, and take your turn at the wheel for an authentic tall ship sailing experience.

More Info Book online now!

Key West Day Sail

Our daily 2-hour afternoon sailing tour fits perfectly into your Key West sightseeing trip. Enjoy an exciting Key West sailing adventure on the glistening crystal blue waters, with the Rover’s signature red sails flying! Look for the abundant Florida Keys wildlife both in the air and sea. Find your inner pirate and join the crew while you hoist the sails, steer the ship and fire the cannons!

Private Charters

Searching for a truly unique Key West sailing experience that is all your own? Charter your own private Key West tall ship sailing adventure. Whether its a few hours to celebrate a special event or an all day adventure, tell us where you want to go and what you want to experience, then climb aboard! For memories of a lifetime, charter a sunset wedding or an overnight excursion. Boca Grand is only 12 miles outside of Key West and is in a world of it’s own. You can even charter the Jolly II Rover for a private party dock side or anchor overnight experience.

Experiences

Key West Experiences

Key West Lighted Boat Parade

Join the Crew of the Jolly II Rover and parade through the Historic Seaport of Key West showing off the ships holiday décor! Enjoy a starry night, a festive atmosphere and thousands of twinkling lights on this entertaining evening cruise. Bring your own choice of food and beverages, bottled water snacks of crackers and cheeses included.

Key West Wreckers Race

The “day of wreckoning” reenacts times in Key West history when wreckers raced to a disabled ship, rescued the crew and laid claim to the cargo! Today, there is nothing to rescue except bruised egos from the last race. Join the Schooner Jolly II Rover for a day of rivalry, fun and radio insults on the high seas! Enjoy an exciting sailing adventure among a multitude of sailing vessels all competing for fun!

Key West Civil War Days

Join the crew of the Schooner Jolly II Rover for this very exciting and famous, annual Battle of the Schooners!! Re-enactors in period costume will be onboard as the Schooner Jolly II Rover defends its position in the harbor against opposing forces from both land and sea! This is a very popular and very exciting event. Seating will be limited to 16 passengers and ear protection will be provided to all passengers.

Currently operating year round out of the Historic Seaport of Key West, Florida, the Schooner Jolly II Rover is the only square rigged, topsail schooner contracted with the Florida National Boy Scouts of America High Adventure Sea Base Program. The Jolly II Rover provides boy scout troops with week long sailing, snorkeling and fishing adventures in the beautiful waters of the lower Florida Keys through the months of June, July and August.

Over the years, the Schooner Jolly Rover has been featured in countless magazines, newspapers and blogs for our iconic red sails and legendary sunset cruises. Read them here.

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Join us on facebook here ., frequent sailor discount.

Many locals as well as visitors are repeat sailors. And we love seeing familiar faces, so we offer $15 off your second sail and your third sail is FREE!

*Within 30 days.

Where to Find Us

Click here for the map.

305-304-2235 BOOK ONLINE

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9 Tours & Activities

Key West Sunset Sail Aboard Schooner America 2.0

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Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand Key Light Tower and more. Enjoy complimentary beverages throughout your sail along with individually plated hors d'oeuvres. Sit back and relax as your captain sails you effortlessly through the emerald green Key West waters and off toward the horizon for a quintessential Florida sunset experience.

Description

Pass By: Mallory Square, 400 Wall St, Florida 33040

Enjoy views of some famous Key West landmarks from the water as the boat sails along the coast and onward into the sunset!

Pass By: Fort Zachary Taylor Historic State Park, 601 Howard England Way, Florida 33040

See the famous Fort Zachary from the water as you sail by.

Pass By: Sunset Pier, Duval St, Ocean Key Resort & Spa, Florida 33040

Enjoy great waterside views of Sunset Pier and other famous Key West landmarks as the captain sails America 2.0 alongside the coastline and onward!

Reservations are REQUIRED for all bookings
Book Your Package On-Line and Receive Your Confirmation
Departure point: Detailed check-in instructions - including the address and parking information if applicable - will be included in your final confirmation email.
Duration: 2 hours (Approx.)
Return Details: Returns to original departure point

What's Included

Complimentary beer, wine, Champagne and soda
Your 2-hour sailing experience aboard America 2.0
Individually plated hors d'oeuvres
Hotel pickup and drop-off

What To Bring

Confirmation Voucher (printed or mobile)
Any required or suggested items listed on your confirmation email.

Additional Info

Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Suitable for all physical fitness levels
We recommend bringing a light jacket as it's often cooler on the water.
Must be 21 years or older to consume alcohol.
Meet at Key West Bight Marina 20-30 minutes prior to your selected departure time to check in at ticket booth and board the sailboat for your sunset cruise

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

For a full refund, you must cancel at least 24 hours before the experience’s start time.
If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
Any changes made less than 24 hours before the experience’s start time will not be accepted.
Cut-off times are based on the experience’s local time.
This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

Average 4.93 out of 5 stars based on 1,121 traveler reviews collected by Tours of Key West and partner sites such as Cool Destinations and TripAdvisor

Still have questions?

We’re here to help. Call Us , " data-help-center="text-us"> Text Us , or Live Chat to speak with a Destination Specialist Product code: C-5395SUNSET

Similar Tours & Activities

Key West Sunset Dinner Cruise

Key West Sunset Champagne Cruise

Key West Sunset Harbor Cruise

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On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Tours of Key West over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

Accessibility

Accessibility modes, online dictionary, readable experience, visually pleasing experience, easy orientation, accessibility statement.

www.toursofkeywest.com
March 22, 2024

Compliance status

Screen-reader and keyboard navigation.

Screen-reader optimization: we run a background process that learns the website’s components from top to bottom, to ensure ongoing compliance even when updating the website. In this process, we provide screen-readers with meaningful data using the ARIA set of attributes. For example, we provide accurate form labels; descriptions for actionable icons (social media icons, search icons, cart icons, etc.); validation guidance for form inputs; element roles such as buttons, menus, modal dialogues (popups), and others. Additionally, the background process scans all of the website’s images and provides an accurate and meaningful image-object-recognition-based description as an ALT (alternate text) tag for images that are not described. It will also extract texts that are embedded within the image, using an OCR (optical character recognition) technology. To turn on screen-reader adjustments at any time, users need only to press the Alt+1 keyboard combination. Screen-reader users also get automatic announcements to turn the Screen-reader mode on as soon as they enter the website.These adjustments are compatible with all popular screen readers, including JAWS and NVDA.
Keyboard navigation optimization: The background process also adjusts the website’s HTML, and adds various behaviors using JavaScript code to make the website operable by the keyboard. This includes the ability to navigate the website using the Tab and Shift+Tab keys, operate dropdowns with the arrow keys, close them with Esc, trigger buttons and links using the Enter key, navigate between radio and checkbox elements using the arrow keys, and fill them in with the Spacebar or Enter key.Additionally, keyboard users will find quick-navigation and content-skip menus, available at any time by clicking Alt+1, or as the first elements of the site while navigating with the keyboard. The background process also handles triggered popups by moving the keyboard focus towards them as soon as they appear, and not allow the focus drift outside of it.Users can also use shortcuts such as “M” (menus), “H” (headings), “F” (forms), “B” (buttons), and “G” (graphics) to jump to specific elements.

Disability profiles supported in our website

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Keyboard Navigation Profile (Motor-Impaired): this profile enables motor-impaired persons to operate the website using the keyboard Tab, Shift+Tab, and the Enter keys. Users can also use shortcuts such as “M” (menus), “H” (headings), “F” (forms), “B” (buttons), and “G” (graphics) to jump to specific elements.

Additional UI, design, and readability adjustments

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Color adjustments – users can select various color contrast profiles such as light, dark, inverted, and monochrome. Additionally, users can swap color schemes of titles, texts, and backgrounds, with over 7 different coloring options.
Animations – epileptic users can stop all running animations with the click of a button. Animations controlled by the interface include videos, GIFs, and CSS flashing transitions.
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Audio muting – users with hearing devices may experience headaches or other issues due to automatic audio playing. This option lets users mute the entire website instantly.
Cognitive disorders – we utilize a search engine that is linked to Wikipedia and Wiktionary, allowing people with cognitive disorders to decipher meanings of phrases, initials, slang, and others.
Additional functions – we provide users the option to change cursor color and size, use a printing mode, enable a virtual keyboard, and many other functions.

Browser and assistive technology compatibility

Notes, comments, and feedback.

(305) 304-7999

The Keys Are Calling & We Must Go

Explore our tours, see the real keys.

Two schooners sailing at sunset near Key West, FL

Wind & Wine Sunset Sail

Sail, Snorkel & Kayak

A couple walks in clear blue waters while holding hands in Key West

Private Charters

4th of July fireworks at night over the water near Key West

Special Cruises

Tour Schedule

We sail every day.

A young couple takes a selfie while enjoying a private sailing charter in Key West with Danger Charters

Prices & Rates

Reserve your spot.

Two women in an orange kayak paddle in calm waters near Key West, FL

Seasick? Not Likely.

We love calm water.

Key West Sailing Charters

What makes us different.

Locally owned and operated for more than 30 years, Danger Charters is all about the Key West sailing experience – wind in the sails, sun on our face, the sound of the waves lapping against the hull.

Our shallow-draft schooners allow us to go where others can’t … and we choose to go where others don’t. We seek calm, crystal-clear water so that you can enjoy the very best of the beautiful Florida Keys. We can’t wait to host you for an unforgettable day of sailing in Key West.

We treat you to the Key West that’s inspired countless paintings and poetry, and show you why locals choose Danger Charters too. Kick back, relax, and be one with the wind and waves … we’ll take care of the rest.

A Danger Charters crew member unties a rope

What We Provide

Calm water for smooth sailing
Excellent food and beverage
No crowds so you can lounge
Experienced captains
Knowledgeable crew
Eco-education opportunities
Top-quality snorkeling gear
Easy to use kayaks

Our Playground

Luke loves to be on the water and is super knowledgeable about the stunning marine life that surrounds Key West. Luke moved to the Keys from South Carolina a little over a year ago, so even when he’s not working he’s out exploring the Backcountry and waterways.

Meet the Crew

Historic Key West Schooners

Schematic of Danger one of the schooners in Danger Charters' Key West fleet

Danger’s Prize

Schematic of Pearl one of the schooners in Danger Charters' Key West fleet

Danger’s Pearl

Learn About Our Boats

Spent my birthday eve sunset sailing with my husband and it was unforgettable! Could not recommend it enough. Such a beautiful time! I would definitely do it again next time we go to Key West. Thank you all for such a wonderful and memorable experience!

Katherine Bejerano — Google

I can’t get over how personal this experience was!!! The group was small which made the experience that much better. Myself, my sister, and my two daughters had the best time! Everyone was so kind and personable! Thank you for a wonderful time! Danger Charters is definitely a must if you are looking for a sail, snorkel, kayak experience for the first time!

Carlota Castillo — Google

We did a full day sail and snorkel trip with about 27 of us and it was perfect! The crew Bryan, Logan, and Alex were informative, attentive, down to Earth, and make a mean pasta salad! They even provided the snorkeling gear and tips on where to look at the reef! Hands down the best trip during Key West! Will definitely book again in the future! Thanks guys!

Michelle Williams — Google

Make Memories To Last A Lifetime

Dream wedding venue 🤩 Did you know that all of our Captains are ordained so they can actually marry you and your special someone on the boat! Checkout our website for wedding options! 💍 💫 #sailinglovers #sailing #chartersailing #thefloridakeys #visitkeywest #keywest #visitflorida #dangercharters #boatlife #boatcharter #keywestwedding

And on a sailboat?! There’s no beating that! 😁 🌅 ⛵️ • #sailinglife #sailing #sunsetsail #visitkeywest #unlockthekeys #keywestsunset #lovefl #keywest #visitflorida #keywestlife #dangercharters

Our beautiful SV “Sarah” in all her glory 🙌🏻

Happy International Women’s Day 👸 Big thanks to our lovely ladies of the Danger crew! Couldn’t do what we do with out ya ;) • #sailinglovers #sailing #chartersailing #thefloridakeys #visitkeywest #keywest #visitflorida #dangercharters #boatlife #boatcharter #internationwomensday #boatgirl

🌅🌅🌅 • #sailinglife #sailing #sunsetsail #visitkeywest #unlockthekeys #keywestsunset #lovefl #keywest #visitflorida #keywestlife #dangercharters

Oh the things you can find on our kayak tour! Morgan here found this spotted sea hare on the sea floor! One of the funnier creatures we have down here because they will ink all over you 🤣 • #sandbar #boatlife #thingstodoinkeywest #visitkeywest #keywest #dangercharters

Escape the chaos of Duval Street and dive into the natural beauty of the Florida Keys! 🌴🛶 Kayaking through the mangroves is an absolute must-do! 🌿 Immerse yourself in nature’s sanctuary and get up close with diverse wildlife! • #boatlife #keywest #thingstodoinkeywest #visitflorida #mangroves #naturelovers #travellife #kayaking

Our online storefront is finally up and running, so be sure to check out our new Danger Merch! ⛵️ The link is in our bio! Also, since St. Paddy’s Day is approaching, we have created some themed clothing for the holiday 🍀💚🍻 • #dangercharters #keywest #visitthefloridakeys #islandlife #keywestmerch #keywestflorida #boatlife

Ready to Start Your Adventure?

March Special – Save 15% off of all Day sails (AM, PM, and Premium) with code SPRINGSAIL15. Save 10% off the Wind & Wine sails with code LUCKY10. Not valid on private charters.

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Friends enjoy a glass of white wine while on a sailing charter with Danger Charters in Key West, FL

Privacy Overview

Key West Sailing Adventure

Private sailing charters, 305.304.4911, [email protected], private sailing charters from key west for up to 6 passengers with various popular charter package choices., experience & explore the american caribbean aboard a sailboat., see our boats.

St. Vitus Dance

Sunset Sailing Charter More info

Half Day Sail More info

Full Day Sail More info

Open Sunset Wedding At Sea Charter Video

Weddings At Sea More info

Open Premium Vacation Sailing Charter Video

Premium Charter Package More info

Key West Sampler Package More info

24hr At Sea Sailing Excursions More info

Stay-Sail Charter Package More info

Choose from three sailboats located downtown in Key West’s Historic Seaport just two blocks from Duval Street. The town is at your feet. There are famous bars and restaurants, beautiful parks, and dozens of attractions to enjoy. The sailboats are docked down the pier just far enough for quiet and privacy.

Sailing and snorkeling is the best fun Key West has to offer. Choose a sailboat to truly enjoy the Key West experience.

Our captains will sail you to the barrier reef to snorkel, take in a sunset, dive a wreck, fishing is an option, visit the dolphin playground. See the beauty this paradise has to offer. One of the favorite charters is the 24 hour Excursion or make it for a several day sailing adventure anchoring out at night. Charter the boat as if you own it selecting a sailing activity with your captain.

Sailing is not just the best vacation activity, it's also the most fun, visit our Key West Sailing YouTube Channel to see all the fun you could be having.

See how you can have the most fun on a sailboat visit our private sailing charters page.

Whether you want a pleasant sail with snorkeling to the barrier reef, an overnight sailing package, or a sailing excursion to the Bahamas. We are ready to unlock your dream vacation. All of our charter options are merely suggestions based on popularity. We can fully customize any charter to meet your wishes. It's your boat, your vacation, we just make it happen.

Some of our guests have expressed interest in learning more about sailing, we're creating new pages just for them. Visit our list of sailing and nautical terms , to know what the pirates are saying. Additional topics will follow soon.

Part of the Hindu Charters Family
(305) 509-1771
[email protected]

Argo Navis is a 75 ft luxury catamaran — the last commercial sailing vessel built in Key West, Florida. We sail year-round from the Key West Historic Seaport offering Sunset Cruises, Brunch Sails, and Day Trips as well as Special Events. All ticketed trips are inclusive of craft beers & cocktails, fine wines, as well as light bites & heavier menu offerings, depending on the trip. Our team specializes in creating and hosting your perfect Private Charter and the vessel is also available as a venue for corporate meetings, classes, summits & seminars.

Argo navis is part of the hindu charters family – sail as you are. .

Join us on the SV Argo Navis, the only luxury catamaran sailing yacht in Key West, for 2 hours of craft food and drink pairings as the sun sets where the Atlantic Ocean meets the Gulf of Mexico. Your sail through the enchanting changing tropical colors of the sky and water includes a selection of craft beers, fine wines, six rounds of charcuterie style passed appetizers and bean-to-bar chocolates chosen by our crew with suggestions from our sommelier. We don’t play any music and never overcrowd the boat so there’s a seat for everyone to enjoy space to stretch out and relax while experiencing the tranquility of a wind driven vessel. A sunset on the water is the original nightly show, and we’ve got the best front row seats.

The Argo also offers a Best of Key West Sunday Brunch, special themed and holiday sails, and private charters for your group or event. From weddings to corporate retreats, chef dinners to birthday and anniversary celebrations to dockside meeting venues, the crew is standing by to custom create your perfect excursion with exquisite attention to every detail.

Sail as you are on the 75’ luxury catamaran SV Argo Navis for an unsurpassed experience. Book direct here on the website or call 305.509.1771 for personalized assistance. Always friendly dog friendly on all our sails. Have more questions about our sailing charters? View our Frequently Asked Questions page here.

Have more questions? See our FAQ here.

What Do Our Guests Say?

See more reviews.

PART OF THE HINDU FAMILY

Hindu Charters is a family-owned, local business sailing out of both Key West, Florida and Provincetown, Massachusetts. Schooner Hindu, one of the oldest, most historic wooden schooners in the Florida Keys, has been sailing out of P-Town since 1946. Built in 1925, Hindu is undergoing a top to bottom historic restoration just in time for her 100 th anniversary. To help with this enormous undertaking, all sails on our luxury catamaran SV Argo Navis support this effort.

Location Of The Boat

Get directions to the boat.

PROUD SUPPORTER

FRIENDS & COMMUNITY PARTNERS

Chesapeake Bay Itineraries
Key West Itineraries
Chesapeake Bay
Virgin Islands
St. Vincent & The Grenadines
Browse our Fleet
Meet Your Captains
Charter Management
Sailing Lessons

Key West Sailing Charters

Experience the beauty and wonder of an unspoiled tropical paradise without ever leaving the Continental United States. Our Key West sailing charter destination is located minutes from all the downtown Key West attractions and Duval Street night life, yet a short sail away from pristine reefs, underwater nature preserves, and uninhabited island locations such as the stunning and secluded Marquesas. Kayak, paddle board, and snorkeling excursions will open to you the offshore beauty offered only in the Florida Keys. Our native Floridian staff knows how to find the best activities on land or at sea, to guide you as you plan a unique and customized getaway.

Our Key West Sailing Charter Fleet

Sailing cats.

Southern Cross

Fountain Pajot Elba 45

Dream Reach

Sugar Magnolia

Seawind 1260

Second sight.

Stay Glassy

Nautitech 40 open.

Ever Summer

Fountaine pajot my44, key west attractions.

Historic Duval Street

One of the most popular destinations on the island of Key West is Duval Street. Visit the Ernest Hemingway Home and Museum where you can take in some history about the writer and meet a legendary six toed cat. If you feel like taking in some nature, visit the Key West Butterfly and Nature Conservatory where there are 50 - 60 different species of live butterflies from around the world. On Duval Street, you can simply take a stroll and hear live music, see art galleries, enjoy coffee shops and great restaurants, or find unique souvenirs at one of the many boutiques.

Romantic Sunsets

Beautiful sunsets are what Key West is all about. Enjoy the soothing ocean breeze, a glass of wine, and relax to the backdrop of the setting sun on your own private catamaran cruise. Watching the sunset has become an integral part of everyday life in paradise. This is one tradition you don’t want to miss!

Crystal Clear Snorkeling

Key West offers many beaches and reefs where you can experience snorkeling in warm crystal-clear water. At Cottrell Key, see the unique sponge garden and large coral reefs. It is also an excellent place to see dolphins, sharks, stingrays, and Goliath groupers. Fort Zachary Taylor is considered one of the best offshore snorkeling spots in Key West where there are a variety of tropical fish species and living coral to see. A favorite among snorkeling enthusiasts is Sand Key Lighthouse Reef. With a remote location and strict no-take policy, the Sand Key Lighthouse Reef is one of the healthiest coral gardens in Florida.

Pristine Sandy Beaches

Craving a drink in your hand and your toes in the sand? Check out the turquoise waters at Smathers Beach. Rental shops are available with beach chairs, shade umbrellas, kayaks, jet skis and much more. Try South Beach for calm, shallow waters that are excellent for swimming and great for families. Higgs Beach is unique for its historical significance. Take a wander around, and you'll find monuments dedicated to the 19th-century slave cemetery located on the site. There is also a pier at Higgs Beach, where visitors can often spot stingrays and other marine species.

BOOK 7+ DAYS IN ADVANCE AND RECEIVE AN ADDITIONAL 5% OFF YOUR ONLINE BOOKING. ENTER PROMO CODE EARLY AT CHECKOUT

305-509-9047

Key West's #1 Rated Schooner Sails

Key west’s award winning schooner cruises, adventure awaits you.

Key West's #1 Rated Day Sail

Sunset Sails

Key west's award winning sunset sails.

Bugeye Backcountry Eco Tour

Private Charters

Charter our historic schooners, historic schooners, that honor the waters of key west.

Schooner Appledore II circumnavigated the world on her first journey. She continues to prove her seaworthiness as she makes the twice-a-year journey between Key West and Camden for daily sailing adventures.

Appledore Star is the last known Chesapeake Bugeye ever built. This unique shallow draft design allows her to navigate Key West’s backcountry with ease on daily eco-tours exploring mangrove islands.

Experience a Key West bucket list experience on one of our historic Schooners. Choose from our award winning Key West Sunset Sail, Key West Windjammer Day Sail, Key West Eco-Tour or start your vacation with our Key West Bloody Mary Sail.

Discover These Great Key West

Wooden schooners.

Step aboard the Appledore II for a true sailing adventure. This two-masted hand-built wooden schooner calls both Camden, Maine and Key West, Florida home. During warm weather months enjoy a scenic sail along Maine’s magnificent rocky coast. When the weather turns cold, the Appledore II heads south and sails Key West’s tropical waters.

see the schooners

Welcome back! We are pleased to announce our official re-opening on June 5th with reduced capacities and additional safety protocols to ensure a safe and enjoyable experience for both passengers and crew. Advanced reservations (book Online or Call) are required. No walk ups are permitted per the City of Key West at this time.

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If you prefer, you can choose to have your computer warn you each time a cookie is being sent, or you can choose to turn off all cookies via your browser settings. Like most websites, if you turn your cookies off, some of our services may not function properly. However, you can still reserve a booking over the telephone by contacting the company’s customer service number directly. Your browser or device may include “Do Not Track” functionality. Sebago Watersports information collection and disclosure practices and the choices we provide, will continue to operate as described in this Privacy Policy, whether or not a Do Not Track signal is received.

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Sunset Cruises
Key West Sunset Cruises

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Beach Rentals
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Bahama Village
C.B. Harvey Memorial Rest Beach
Dolphin Playground
Fort Zachary Taylor State Park
Higgs Beach
Key West Cemetery
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The Southernmost Point
Spring Break in Key West
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Christmas in Key West
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Valentine’s Day Key West

Recommendations

Top 10 Key West Best
#1 Staff Picks
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Best For Culture & History
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Getting Around
Shopping & Gifts
Things To Do with Kids

Key West Wind & Wine Sunset Sail

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running.... Read More

Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location

Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location

Looking for the perfect way to end your day? Join us aboard a 45ft Corinthian powercat, and ride in comfort with this relaxing, catered cruise... Read More

Key West Sunset Champagne Cruise

Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy... Read More

Key West Sunset Dinner Cruise

Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar.... Read More

Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar

Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran... Read More

Key West Schooner Sunset Sail with Hors D’oeuvres and Full Bar

Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and... Read More

Key West Catamaran Dolphin Watch & Sunset Sail

Key West Catamaran Dolphin Watch & Sunset Sail

Set sail from Key West's Historic Seaport for a thrilling dolphin watch and famous Key West sunset sail aboard a luxury catamaran with premium wines... Read More

Key West Sunset Snorkel Sail

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and... Read More

Key West Dolphin Watch Sunset Snorkel Cruise

The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous... Read More

Sunset Sip & Sail

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •... Read More

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Key West Private Wind & Wine Charter (for up to 30 guests)

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running. See the sunset on... Read More

Key West Sunset Cruises Overview

A Key West sunset cruise is a vacation must-do that adds an unforgettable experience to any Key West visit. Choose a graceful sailing schooner, a sleek modern catamaran, or a roomy dinner cruise liner with live music and all the trimmings – this curated selection of the best Key West sunset cruises offers good times set against one of nature’s grandest spectacles.

Depart the harbor in the late afternoon to enjoy an evening on the water, or combine dolphin watching, snorkeling, or a glass-bottom boat tour with sunset and the perfect end to another day in paradise. Key West sunsets are famous for highlighting nature’s grandeur as the sun sinks below the broad ocean horizon and brings on dramatic color changes of a range and intensity not seen on land. The unobstructed fetch of the light, atmospheric moisture, and other refractory factors combine to produce awe-inspiring natural beauty.

Add a chilled beverage and a loved one to share the occasion and the result is sublime. Click on a selection below to learn more about the most popular Key West Sunset Cruises.

Frequently Asked Questions

The answers provided below are based on answers previously given to customers' questions.

Q: What type of boats are used for Key West Sunset Cruises?

A: The diversity of available sunset cruise vessels is one of the things that make Key West Sunset Cruises so special. Guests who enjoy sailing can choose a 65-foot skipjack schooner with authentic lines that replicate the sailboats used by 19th century Florida Keys fishermen and wreckers. Or a modern sailing catamaran with the stability, speed, and generous deck space these craft are known for. Power catamarans are fast and smooth, perfect watersports or dolphin-watching platforms. And of course, enjoying a buffet dinner and cocktails aboard a 65-foot custom party catamaran should be on everyone’s bucket list. For a wedding, anniversary, or other special occasion, try a private charter to have a sail or power yacht all to yourself.

All the boats used for these popular Key West Sunset Cruises are top-of-the-line designs built for safety, comfort, and fun on the waters around Key West. The United States Coast Guard regularly inspects every Key West Sunset Cruise boat, and all required safety equipment is aboard and properly updated at all times. This is luxury sunset cruising at its best, with expert local captains and crew members, high-tech navigation gear, and the latest in quiet, efficient, low-emission engines. Plus, there are those added touches to enjoy like room for cocktail and wine service, deck space for top local musicians to perform, and even a bit of space to dance on some cruises.

Q: What makes a Key West Sunset Cruise so special?

A: Something about sunset in a tropical island location inspires people to a greater appreciation for what is normally a simple daily event. The famous and elusive Waikiki sunset “green flash” draws hundreds of camera-toting tourists to the Kalakaua Avenue beach walk each evening. Maui has Mt. Haleakala, the “House of the Sun” with sunsets worth an hour drive up the mountain. Beach bar decks in Phuket Thailand get packed as early evening comes on. And sunset in Key West is definitely a big deal whether seen from land or water.

Mallory Square and the nearby anchorage waters have been a hub of activity in Key West for over two hundred years, and when hippies arrived in town during the late 1960’s, they discovered that Mallory Pier offered a perfect wide-open view to the west. The custom of celebrating the amazingly colorful ocean sunsets took hold, and now Mallory Square and the Key West sunsets are both world famous.

Visitors have been boarding boat tours out of the harbor near today’s Mallory Square since the mid-19th century. With quiet, unobstructed on-deck views, the blazing orange, red, and purple clouds along the horizon and the awesome disc of the sun visible as it slides out of sight captured attention very early on. Now, modern vessels are able to provide visitors with a nice range of specialized sunset-watching cruises to suit any taste, and the best way to find out why Key West Sunset Cruises are so special is to come aboard and try one (or more).

Q: Which Key West Sunset Cruise is best for me?

A: The only easy choice among the many popular Key West Sunset Cruises is deciding to go on one. After that, the variety of attractive options may easily lead a visitor to decide that the only solution is to enjoy more than one sunset on the water! But if a choice of just one (or two) must be made, the best strategy is to consider what you like best and who is joining you for what could easily be the highlight of any Key West visit.

Naturally, the idea of gliding smoothly over turquoise water under sail while toasting a perfect day with a cold beer, glass of wine, or cocktail is very tempting. A Sunset Sip & Sail or Premium Sunset Sail with Hors D’oeuvres and Full Bar will provide a perfect happy hour start for a couple planning an evening on the town.

For an active family, or anyone who enjoys the water, taking an afternoon snorkeling trip that winds down with a beautiful sunset (and beverages) offers the best of both worlds. A Key West Sunset Snorkel Sail is just the ticket. Nature lovers should try a Glass-Bottom Boat Tour Sunset Combo or take the Dolphin Watch Sunset Snorkel Cruise.

Looking to party with some reggae or just enjoy live music and a cocktail hour at sunset? Take a look at Rum n’ Reggae or the Sunset Party Cruise. The award-winning Key West Wind & Wine Sunset Sail is notable for its pairing of fine wines and craft beers with gourmet appetizers. Special occasions (and every Key West sunset is special) call for a Sunset Champagne Cruise or Dinner Cruise. And for the ultimate in luxury, gather family and friends or just one significant other on a 65-foot schooner and sail away on a Key West Wind & Wine Private Charter.

Q: What kind of wine is served on the Key West Wind & Wine Sunset Sail?

A: Looking for a sunset cruise with a focus on fine wine to go with the fine view? The Key West Wind & Wine Sunset Sail is a legend with locals and visitors alike. This elegant and awesome sunset cruise has pulled down top ratings on Trip Advisor for several consecutive years in addition to earning a Top Sunset Cruise designation (one of the top 2 in North America) from Coastal Living Magazine. The Wind & Wine is a cruise that stands above the rest because it is one of very few sailing excursions in the United States that offers a selection of “real” fine wines from America and around the world.

A small group will gather on deck beneath the billowing sails to enjoy an intimate atmosphere, tropical music, and the incredible Key West sunset along with 8 different wines from around the world and 5 types of domestic and imported beer. There are usually 4 red and 3 white wines plus a champagnoise open for the tasting. The charcuterie and cheese board goes far beyond simple sailors’ rations to deliver the perfect wine pairings with Dill Havarti, Smoked Gouda, fresh Mozzarella, and Brie cheeses. Caprese skewers, summer sausage, honey-drizzled green apple slices, fruit, water crackers and more make for the ultimate water-borne wine tasting session.

Q: Skipjack schooner or catamaran – which one is best for a sunset cruise?

A: Sailing schooners and sailing or powered catamarans are the two most popular Key West sunset cruise vessels. In fact, these are the most commonly used craft for all types of Key West water tours from Backcountry snorkeling and kayak tours to glass-bottom boat rides. The reason for this is simple – skipjack-style schooners and catamarans are both shallow-draft boats that are well-suited to navigating the sandbar- and reef-filled waters around Key West.

Skipjack schooners were originally designed for harvesting oysters in shallow Chesapeake Bay. Adopted for use by 19th-century Florida Keys wreckers, sailors who would race out to salvage cargo from ill-fated ships caught on the reefs around the Keys, skipjacks became very common in local waters as general working and fishing boats. Modern catamarans are adaptations of ancient Polynesian boat designs used by sea-going peoples who lived on tropical islands ringed by shallow coral reefs and lagoons. The ability to skim through the shallows and land directly on the beach was critical. Known for their stability and versatility, today’s catamarans are the fastest and shallowest-running boats on the water.

Both types of vessel provide a safe, comfortable ride and can take guests to the best places to sightsee and play in Key West waters. Do you enjoy a touch of history and the romance of a tall ship under sail? Then a schooner would be a good choice. These classic ships have been sailing out of Key West for over 200 years, and guests who come aboard a Key West schooner today are in for an award-winning luxury sunset cruise.

Catamarans also move very gracefully under sail, but a key difference is that the cat’s deck remains level at all times because the vessel does not heel (lean over under the wind power) like a single-hull sailboat. A catamaran can also offer more wide-open deck space between the two hulls. This allows for seating at tables, live music and dancing, and ease of movement around deck for enjoying the view and taking pictures. The broad, flat deck also makes the catamaran a great play boat for an afternoon of watersports and sunbathing.

Schooners and catamarans are both a lot of fun on the water, so the choice between them is mainly about a guest’s personal preference. Planned activities for the sailing trip as well as any physical limitations and the need for ease of movement should also be considered. Of course, many Key West visitors end up going out on both types of vessel to enjoy not only beautiful sunset cruises but the many other opportunities for fun on and in the water that have made Key West a world-famous tropical vacation destination.

Q: What are the best options for Key West Sunset Cruises?

A: According to verified reviews on Cool Key West and TripAdvisor, the best Key West Sunset Cruises are:

Q: What are the best kid-friendly options for Key West Sunset Cruises Activities?

A: According to verified reviews on Cool Key West and TripAdvisor, the best kid-friendly Key West Sunset Cruises are:

View all kid-friendly Activities →

Q: Which Key West Sunset Cruises have Instant Confirmation?

A: Key West Sunset Cruises with Instant Confirmation include:

View all Activities with Instant Confirmation →

Q: Which Key West Sunset Cruises have Free Cancellation?

A: Key West Sunset Cruises with Free Cancellation (in most cases up to 24 hours in advance of your activity date, check the specific activity page) include:

View all Activities with Free Cancellation →

Q: I need a ride! Which Key West Sunset Cruises include Hotel Pickup?

A: No problem. These Key West Sunset Cruises include Hotel Pickup:

View all Activities with Hotel Pickup →

Things To Do in Key West

Key West Beach Rentals
Key West Bus Tours from Miami
Key West City Tours
Key West Day Trips
Key West Dinner Cruises
Key West Do It All Tours
Key West Dolphin Tours
Key West Private Boat Charters
Key West Eco Tours
Key West Extreme Sports
Key West Fishing
Key West Large Group (7+) Fishing Charters
Key West Deep Sea Fishing
Key West Flats Fishing
Key West Light Tackle Fishing
Key West Ghost Tours
Key West Glass Bottom Boat
Key West Inshore fishing
Key West Jet Ski Tours
Key West Kayaking Tours
Key West Museums
Key West Parasailing
Key West Sailing Tours
Key West Scuba Diving
Key West Scuba Instruction
Key West Shore Excursions
Key West Sightseeing Tours
Key West Snorkeling Tours
Key West Trolley Tours
Key West Vehicle Rentals
Key West Electric Car Rentals
Key West Golf Cart Rentals
Key West Scooter Rentals
Key West Walking Tours
Key West Water Sports
Key West Water Tours
View all Things To Do in Key West

Key West Attractions

Bahama Village Tours & Tickets
C.B. Harvey Memorial Rest Beach Tours & Tickets
Coral Reef Tours & Tickets
Dog Beach Tours & Tickets
Dolphin Playground Tours & Tickets
Fort Zachary Taylor State Park Tours & Tickets
Higgs Beach Tours & Tickets
Key West Cemetery Tours & Tickets
Key West Marine Park Tours & Tickets
Smathers Beach Tours & Tickets
South Beach Tours & Tickets
The Southernmost Point Tours & Tickets
View all Key West Attractions

Key West Calendar

New Year's Eve in Key West
Celebrate Valentine's Day in beautiful Key West!
View all Key West Calendar

Key West Recommendations

Best For Culture & History
Cool Key West #1 Staff Picks — What would a local do for fun in Key West?
Getting Around Key West
Key West Shopping & Gifts
The Best Key West Tours & Activities For Relaxation
Things To Do in Key West with Kids
Top 10 Key West
View all Key West Recommendations

Sorting, ranking, and search results

Cool Key West wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Cool Key West over a 12-month period.

Accessibility

Accessibility modes, online dictionary, readable experience, visually pleasing experience, easy orientation, accessibility statement.

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March 22, 2024

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305-304-4800
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Marriott Beachside 3841 N. Roosevelt Blvd

Private Key West Boat Tours

Memories to last a lifetime, explore key west like never before.

Amazing Destinations

World-class Key West destinations just a short boat ride away

Experienced Captains

Trust our experienced captains so you can focus on total relaxation

Super Fast Booking

Real time availability and instant confirmation for your upcoming trip

Affordable rates

We’ll make the most of your Key West vacation without breaking the bank.

Private boat tours in the heart of paradise

Key West Boat Trips offers the perfect launch pad for your next Key West vacation. Leave the crowds behind and enjoy a day out on one of our tour boats or spend an evening kayaking the mangroves. Choose from snorkeling, swimming, sandbar hopping, or even a sunset dinner cruise! We’ll take you to exciting destinations like Mud Keys and Boca Grande – where you may see one of Florida’s most famous resident animals: dolphins!

keywestboattrips

Our guided key west tour packages, let's go to your happy place, hopping sandbars in key west, 1 hour boat ride each way 1 hour on sandbars, 1 hour boat ride each way 2 hours on sandbars.

On this Key West boat tour, you get to see not one, but several different sandbars. We’ll take only 25 minutes to go there on our epic excursion–but we’ll stop for as long as you want at those that interest you the most. All-in-all, it’s an experience unlike anything else offered here!

See the mangrove trails of Mud Keys and go mingle with locals at Snipe Point sandbar after. You will not want this day to be over.

Starting From

for up to 6 people

Key West E-foil Rides

30 minute boat ride each way 2 hours e-foil session.

Now you can experience surfing’s newest frontier, the electric hydrofoil surfboard on one of our Key West boat tours. Take a 30 minute boat ride to the protected area with calm and deep water. Enjoy a 2 hour session on Lift foil model 3 electric powered hydrofoil surfboard while being coached by one of our experienced captains.

for up to 2 riders 6ppl total on the boat

Sandbar Trips for Large Groups

If your group is larger than 6 and you have a hard time finding a boat ride to the sandbars because of the 6 passengers limit, we are here to help. You can book our 2 identical Hurricane 27 foot deck boats and our captains will drive them side by side so you can take cool photos and they will raft up the boats on the sandbars so you can enjoy and share this amazing time together.

for up to 12 people

Key west Sunset Cruise

Sunset Cruise in Key West! We are headed to the sandbar and beyond, our skipper will take us out for a private boat tour into the backcountry waters. Watch as we anchor over the sandbar, reaching deep enough for you to jump from just above waist high water and get some awesome pics with the sun setting behind you – it’s really something special.

Key West Dinner Cruise

This Key West Dinner Cruise is the perfect way to enjoy beautiful scenery and a fresh seafood dinner with wonderful friends or family. The whole cruise experience includes an experienced captain taking you to the best location in Key West, with him cooking while you play in shallow turquoise water. You will thoroughly enjoy this unique adventure that people never forget.

Key West Lunch Cruise

This Key West Lunch Cruise starts off by getting on a boat ride that will drift through the beautiful backcountry waters. The boat will dock at its very own sandbar location where you are free to walk around or have an enjoyable swim in clear, shallow water. After snorkeling or simply staying on the boat, we will serve you freshly made lunch!

Mud key Mangrove Safari

Mud Keys Mangrove Safari will have you feeling like a world explorer in our own backyard. After getting onto the boat, we’ll take you for a 30-minute cruise of backcountry waters to Mud Key Sanctuary! Upon arriving there, enjoy nature surrounding you and take pictures while soaking up the sun. You can walk around on the sandbar and swim if you’d like or just soak in all the gorgeous sights the area has to offer.

Boca Grande Island Time & Snorkeling

If you are looking for some beach time on a remote island far far away – this boat trip is for you. Stop on the way for sponge garden snorkeling in just 5 feet of water. At the Boca Grande destination, you’ll take a break from your phone as you will not have any service there. Walk down the beach and enjoy looking at the beautiful turquoise colors of the water surrounding you. If you will feel like exploring further – we will take you near the neighboring islands Woman Key and Ballast Key for some more breathtaking sights.

Key West Private Boat Charters

30-45 minute boat ride each way, 1.5-2 hours anchored on the sandbar.

Let us bring your family to that magical Key West beach that seems to only exist in calendars and magazines. Sit back, relax, and let the professional captains at Key West Boat Trips take you on backcountry excursion that you’ll never forget. With dozens of world-class destinations, just a short boat ride away, you’ll see why it’s one of the best things to do in Key West.

Key West Dolphin Swimming

Key west glass bottom boat, availability : year round, what our clients say.

Key West Boat Trip Destinations

This destination is only a short boat ride away. After just 30 minutes boat riding, we arrive at a mangrove maze made out of series of islands approximately 11 miles northeast of Key West. We will park our boat somewhere knee deep shallow, over a nice sandy bottom – so you can walk around and take pictures, swim or snorkel in turquoise water and sandbars.

Boca Grande

Do you want to see some of Florida’s most beautiful beaches? If so, then the Key West National Wildlife Refuge Island is one stop that should not be missed. It has a gorgeous natural beach and is 15 miles west of Key West. On your way there, you may spot dolphins playing in the water! We can also stop at the sponge garden off one of the islands for some snorkeling. The water here is only 5 feet deep, perfect for families who are looking for an adventure without getting too deep!

Snipe Point

The sandbar at Snipe Point is a popular destination for locals who spend their weekends boating. This island, often called “Snipes” – is extremely hard to find so boat rentals are unlikely to invade your space. You will be surrounded by locals and their families looking to get away from the hustle and bustle of city life on this gorgeous beach area.

Boat Rental Vs Key West Boat Trips

Private boat tours are a great way to see the Florida Keys! The shallow waters can be dangerous for first timers, so it’s best if you let us do the driving! 🙂

Basic Boat Rental

Half day $450 plus fuel average cost of deck boat rental
Boating experience necessary
Very plain and basic boat with low HP motor
High risk of running aground in very shallow waters therefore possibility of extra cost to cover damages
Credit card hold for $1000+ to cover potential damages
Not likely to get to pretty locations as it takes knowledge of local waterways
You'll need to fill up the cooler with beverages

Key West Boat Trips

Half day $600 with fuel included
No previous boating experience needed
High end premium boat with 300HP motor
With the experienced captain driving no risk of running aground
No additional security deposits or credit card holds
Guaranteed to go to the prettiest destinations around
Cooler full of bottled waters and sodas topped with ice included

FREQUENTLY ASKED QUESTIONS

Most frequent questions and answers.

It has a flushable marine toilet for liquids only. The boat also has fresh water rinse so you can rinse yourself from salt water.

To some extent – yes. Sometimes we will have to because the weather isn’t always ideal and we want to stay in shallow, calm waters to keep the trip enjoyable.

No. All our trips are private. Just you, your loved ones and our captain.

Absolutely. Our boat has a premium amplified 9 speaker audio system and you can play music from your phone via Bluetooth.

We have an iced cooler with bottled waters and sodas. You’re welcome to bring your own drinks, beers and snacks.

Unfortunately not. We are limited to 6 passengers per our license and each child counts as one just like adults.

Yes. We can subcontract another boat for you with another captain from a trusted vendor. We would run side by side and raft up on the sandbar so you can spend that time together.

There is always a chance for that and we often do, however we can’t promise that you’ll see them because they swim around freely and do not hang out in the same place.

We do not. We are not a fishing charter and we think that our boat is just too pretty to have smelly fish guts all over it.

48hrs before the scheduled boat trip to get a full refund if you happen to change your plans. All our trips are weather permitting so we reserve the right to cancel your trip if we don’t think that conditions are safe – in this case you would get full refund also.

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Book your next trip

Trust the premier water sports operator in key west to take you for the trip of a lifetime.

At Key West Boat Trips we take your dream Florida Keys vacation and make it a reality. Let us bring your family to that magical Key West beach that seems to only exist in calendars and magazines.

Important Links

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Sandbar Trips Site

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(305) 304-4800

Free Trips For Kids • 5 & Under • 305-296-2554

Sunset Cruises & Boat Tours

In key west, sunset cruises in key west.

Sunset Watersports is your one stop shop for Key West sunset celebrations. We have the island’s only sunset dinner cruise, an incredible sunset sailing experience or even an action packed sunset snorkeling trip.

Key West’s Best Sunset Sail:

Set sail and explore the beautiful waters of Key West! Enjoy a romantic sail with your loved one, experience the world-famous Key West sunset with a live tropical musician, open well bar & a great selection of appetizers.

Key West’s World Famous Sunset Dinner Cruise:

Climb about the world famous Party Cat catamaran for a night you won’t forget. Guests enjoy a delicious tropical food buffet made fresh in our on-board kitchen. Enjoy an unlimited open well bar & on of the island’s best live musicians as they set a true island vibe as you discover Key West’s legendary sunset.

Snorkel The Reef At Sunset:

Looking for a little more adventurous sunset experience? Look no further than this sunset snorkeling combo. We will take you to the best snorkeling location then open the bar and guests get unlimited draft beer & wine as we cruise around to enjoy the sunset cruise. Book your cruise online below ↓

Key West Sunset Dinner Cruise

Clock 2 hours
Users All Ages

Enjoy a beautiful Key West sunset with a tropical food buffet, live music, and an open well bar! Take in the unbeatable views as you groove into the sunset.

Kids go free!

Sunset Sip & Sail

Grab a tropical mixed drink and dance to a live performance while enjoying a legendary Key West sunset. Includes delicious appetizers!

Sunset Snorkel Combo

Clock 5:00PM or 5:30PM
Clock 3 hours

Join us for a beautiful late afternoon cruise out to the barrier reef for a refreshing dip in the crystal clear waters, then top it all off with a gorgeous sunset cruise through the harbor. This trip includes draft beer & wine.

Seasonal Cruises:

Fourth of july fireworks sail.

Clock 1.25 hours

Celebrate the Fourth of July from the water! Grab a tropical mixed drink and dance to a live performance from one of Key West’s best entertainers while enjoying a legendary Key West sunset.

Key West & Stock Island Lighted Boat Parades

Join us for one of the most memorable nights on the water, Key West’s Lighted Boat Parade. This is your chance to ride in the parade. Includes draft beer, wine, champagne, appetizers & live DJ.

This was a great sunset cruise experience. The boat was clean and accommodating. The view of the Key West sunset was spectacular. The drinks were delicious and plentiful. I would highly recommend this trip!

It was so much fun!! Highly recommend doing this with your friends and family. We had a blast. Honestly well worth it. Jake even took photos for us and sent them to each group!

Our family had an amazing time on the sunset sip & sail and would definitely recommend Sunset Watersports to others. All staff were fun, informative, and my daughters had a great time. Overall, an amazing company to choose for some fun on the water!

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Schooner America 2.0

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Sightseeing Cruise

Book Now Call to order 305-293-7245

Step aboard our classically designed yacht and enjoy a boat ride out into the emerald green waters of Key West. Take in the magic that Key West has to offer with a glass of Champagne in hand, the wind blowing in your hair and dolphins surfing off the bow of our boat. Kick back and feel this beautiful schooner as it dances through the water.

Jump aboard a Key West day sail for an afternoon. Learn the hidden secrets and wonders of this famous little Island. Whether you join us for a Key West sunset cruise or a day sail you are sure to feel as if you are at home. Our crew will dazzle you with their hospitality give you a lasting memory on your Key West sightseeing boat tour.

Key West Brunch Sail aboard the Schooner America 2.0 with guests in the cockpit enjoying food

-->Christmas Day Brunch Sail aboard Schooner America 2.0 -->

Are you dreaming of a crystal clear, blue Christmas? Then, spend your Christmas morning aboard the Schooner America 2.0 for a brunch sail that you and your loved ones will never forget! Start your day with complimentary mimosas, bloody mary’s, or champagne as you sail into the Christmas spirit. This two-hour sail includes a fully-catered brunch that will be sure to help you start Christmas day the right way! On this peaceful holiday sail, you can relax to the natural sounds of the wind and waves, and appreciate the beauty of Key West during the holiday season. (Call us directly to save 6% online processing fee)

Schooner America 2.0 sailing in the morning sunlight for a Key West Mimosa Sail

-->Private Morning Sail on Schooner America 2.0 -->

Step aboard the stunning America 2.0 for a Key West Morning Charter. This 1.5 hour sail is available to book privately with your close friends and family. Start your day off right and take the helm and experience the power of this sailing machine or sit back and relax as you sail smoothly through the crystal clear waters of Key West. Either way and above all, it doesn’t get much better for a morning sail in Key West. Options to extend your trip are available. Charter includes soda, juice, and water. Bar and food packages are available upon request. (Call us directly to save 6% online processing fee)

-->Classic Day Sail aboard Schooner America 2.0 -->

It is true! When in Key West you must soak in the sun while you do some classic Key West day sailing. We think the best way to spend an afternoon is to take to the water on the Schooner America 2.0 for a Key West Day Sail! Named after the first boat to win the America’s Cup in 1851. Our stunning 105-foot sailboat features teak decks, mahogany trimmings, and ample seating. There is over 3,600 square feet of sail that will propel you smoothly through the crystal green waters of Key West. We boast a full bar on board which is available for credit card purchase. Soda and water are complimentary. Guests are encouraged to bring aboard their own picnic lunch! (Call us directly to save 6% online processing fee)

A large schooner sailing in Key West with the sun peaking through the sails for a Key West Sunset Sail

-->Key West Sunset Sail on Schooner America 2.0 -->

Enjoy the best sunset sail in Key West on the Schooner America 2.0! Take in the vibrant colors of Key West’s famous sunset as you sip complimentary champagne. On this Key West Sunset Cruise, you will magically glide through the crystal clear surrounding waters whilst being taken care of by our professional and friendly crew.

This two-hour Key West sunset cruise features complimentary champagne, wine, beer, soft drinks, and water and passed hors d’oeurves- veggie crudite, cheese and crackers, and shrimp cocktail. There is a cocktail bar on board for purchase. Sit back and relax while Schooner America 2.0 plies effortlessly through the turquoise green Key West sailing waters and off towards the horizon for the quintessential Key West Sunset experience! (Call us directly to save 6% online processing fee)

Stern of the schooner America 2.0 with the sails raised and the Captain Turned around waving while sailing for a Key West Wreckers Race

-->Wreckers Race aboard Schooner America 2.0 -->

All hands on deck! If you enjoy a good sailboat race, it is an absolute must for you to sail on board the Schooner America 2.0 for the Key West Schooner Wharf Bar Wrecker’s Cup Race!

A little history…back in the days of old Key West, ships from afar often ran aground on Sand Key Reef. When all the scallywags in Key West heard there was booty to be had, they jumped in their boats and raced to the reef. The first one there could claim the ship’s cargo! Arrggh!

Today, we celebrate this Key West tradition annually with a set of monthly races from January to April. It all starts with the firing of the cannon at 1:00 PM. Enjoy the excitement aboard Schooner America 2.0 as we race to defend our title of fastest schooner in Key West!

One round of beer, wine, champagne, and a boxed lunch are complimentary with your ticket purchase. Purchase a Beverage Package during the booking process, or additional drinks for credit card purchase while on board. (Call us directly to save 6% online processing fee)

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See our calendar of events, private yacht charters.

Sail out into the emerald green waters of Key West and impress your guests. Step aboard the legendary Schooner America 2.0 for a private charter. This yacht is perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

PUBLIC EVENTS

Sail out into NY Harbor and impress your guests. Step aboard one of our classic vessels for a private charter. These yachts are perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

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Key West Sailing Tours

If you’ve spent any time down here in Key West , you’ve probably taken note of the impressive selection of yachts, schooners and stunning sailboats moored in the harbor. Key West has been a sailing destination for hundreds of years, so it’s no wonder that key west sailing tours are some of the most sought after tours on the island. You may have spent some time out there on the high seas during a snorkeling or dolphin excursion , but key west sailing tours are dedicated to showing would be sailing enthusiasts what it’s really like to feel the wind at your back. You could spend any number of Key West’s beautiful sunny days lounging around on a beach, but why when the alternative is climbing aboard a spectacular vessel like the Schooner Appledore II. Spend the day out on the Appledore, a 19t century replicate providing a premium sailing experience. An experienced crew will whisk you off into the horizon, and while you enjoy the gentle rocking of the schooner, you will be treated to unlimited beers, wine, homemade sangria and soft drinks, all free of charge. Key west sailing is the perfect activity for families, groups, families, and if you want to make new friends, come single!

Best on Key West's Island Ting allows you to explore the most-viewed coral reef in the world and then kayak through the mangroves of the Key West National Wildlife Refuge. We'll provide breakfast, lunch and all the equipment you need for a relaxing day of exploration and animal watching. From the exotic reef coral and fish to the endangered species found in the mangroves, there's never a dull moment on the Island Ting tour.

Enjoy a day of snorkeling and kayaking the way only Best on Key West can provide. You get to see it all on the Island Ting tour ━ the spectacular coral reef and the canopied mangroves in Key West’s backcountry. For a relaxing and amazing adventure, you can’t go wrong with our Island Ting tour.

Best on Key West knows how to start the day right. We’ll depart for the Great Florida Reef on the Flyer, a 60-foot sailing catamaran. Passengers will enjoy a wonderfully homemade continental breakfast, which includes cinnamon rolls, cheese toast, yogurt parfaits, and assorted juices. During the 7-mile sail to the reef, our crew will provide you with the necessary snorkeling gear including a mask, snorkel, and buoyancy compensator. The crew will also demonstrate the proper way to use the equipment and give instructions on snorkeling safety. All of our gear is sanitized and safe to use.

Explore Under the Sea

Then the real adventure begins. For an hour, you can swim among the amazingly colorful fish and marine life in this exotic habitat that is unparalleled in the United States. The reef is home to hundreds of different species of fish, turtles, coral, sponges and mollusks, ensuring you never know what you’ll see next! This area is visited by millions of people every year, and we know that you’ll want to return every year to catch another glimpse.

When the snorkeling has concluded, our next stop is the Key West National Wildlife Refuge for lunch and kayaking. Our buffet, prepared and served by our island-famous catering company, includes peel-and-eat shrimp, fried chicken, roast beef slider with sauce on the side, pasta salad, and cookies. Once you’ve digested the tasty meal, we’ll lead you on a guided tour of the backcountry mangroves.

Glide on Sparkling Water

Hop into a kayak and get ready for a look at the local wonder and beauty the Key West mangroves offer. You’ll see a plethora of fauna and flora as many different species live in this Wildlife Refuge. Great White herons, Green herons, Great Blue herons, Osprey and Reddish Egrets make their homes and nests in the mangroves. Keep your eyes open for endangered species like Brown pelicans, Key deer, American crocodiles, Hawksbill sea turtles, Atlantic Ridley sea turtles, Peregrine falcons, West Indian manatees and so much more.

As the tour comes to an end and we set sail for Key West, we offer complimentary beer, wine and our homemade sangria to help you relax and reflect on all the wonder and splendor you experienced during the tour.

Child (11 and Under) $ 89 95
Adult $ 119 95

Head into the beautiful back country area to the north of Key West where you will find the most beautiful nature reserve in the keys. Kayak through the mangroves and wildlife, or jump into the water to explore the fascinating world underneath the water's surface.

This trip departs aboard one of our beautiful and awesome Skipjack sailing vessels, the Danger. Skipjack boats like the Danger are perfect for sailing as they come equipped with a large sail area and are designed in a shallow way to allow for optimal sailing. This is one of the best ways to sail through the beautiful clear waters of Key West. And this boat does more than just sail! Guests can enjoy snorkeling, kayaking, a guided tour, and complimentary snacks, soft drinks, and beers.

The snorkeling part of this trip takes you to one of the best spots on the coral reef. The Danger can take guests to places other larger boats cannot. Snorkeling locations on the reef are chosen on the day of your trip depending on factors like weather conditions and the tides. This will ensure that you and your party are able to go on the safest and best snorkeling trip possible for you on any given day, with the ability to enjoy full visibility and a smooth ride free of seasickness.

The kayaking bit of the tour takes you to the beautiful and exotic Mangrove Islands, home to many mangroves (which are the only trees that can grow in salt water). A tour guide will lead the way through the islands explaining biological and historical facts and answering any of your questions.

Kayaking is both easy and fun and allows you to explore the environments of Key West's backcountry in a very unique way. The guides will also help you learn how to properly maneuver your kayak. While kayaking through the Mangrove Islands, you will learn and see for yourself this truly unique island ecosystem. You will be able to explore the tropical environment on your own and come close to a variety of wildlife in their natural habitats. Some common animals that are seen include all sorts of birds, rays and sport fish.

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Explore the shallows of the Key West National Wildlife refuge aboard a beautiful sailing vessel. This boat features a combination of snorkeling, a fabulous lunch, kayaking the remote islands of the keys, and relaxing on remote private sandbars.

An American sailing vessel, The Dangers Prize, will be the craft that sails you off into the wild, blue, beauty of the sea. The Dangers Prize is what's known as a Skipjack boat. Originally designed to comb oyster beds during the 19th century around the Chesapeake Bay, these boats would sail down to the Florida Keys to double as fishing boats.

Skipjacks are designed in a shallow manner that offers a large sail area. providing the perfect environment for backcountry sailing. You will experience a unique pleasure as you discover the unseen natural beauty of the Florida Keys under a billowing sail. Despite the wind or the calm weather, you will find yourself fully protected from the waters in your shallow vessel as it guides you through one of nature's most picturesque areas.

On your backcountry tour, you will only be visiting the very best snorkeling sites available. We have access to sites that are often inaccessible to others. Sticking to the areas that are only known by the locals, you will have the chance to view the best areas based on the day of your tour.

Depending on exactly when you go on your tour, the location will be chosen according to the conditions of the tide and the wind. You will be free from hazardous or overly rough waters during your backwater country snorkeling expedition. Allowing you to visit calm waters ensures visibility and removes the possibility of any form of seasickness for you and your group.

In the colder, winter months, wet suits are offered to our guests free of charge. Additionally, prescription strength masks will be offered during these months. In an effort to run a family-oriented business, we go the extra mile to treat you as we would a family member or a close friend. It is our goal to protect you and see that you have an enjoyable trip, which means you will be exposed to only the calmest, crystal blue waters of the sea.

The Mangrove Islands await you in this backcountry kayaking expedition. You will have chance to travel with a knowledgeable and friendly guide that will help you explore the vast and wondrous islands. As you explore the area you will experience all there is to see in this sensitive yet beautiful ecosystem on Mangrove Island. Canopied canals serve as your stream, as you paddle through the beautiful ecological wonder and view tropical birds, sharks, sport fish, and other plants and animals.

Do not give it a second thought if you have never been in a kayak previously. We offer the top of the line sea kayaks. These stable vessels will suit anyone no matter their age or experience level and with the help of your trusty companion guide, you will be sure to be paddling with the best of them in no time!

Adult $ 134 00
Child (4 - 12) $ 109 00

Price Match Guarantee

Found a better price online ? We'll Price Match It.

WE WON'T BE BEAT ON PRICE!

In fact, our prices are up to 56% Cheaper*

Best On Key West is the #1 Tour and Activity Concierge in Key West

To prove it we are matching all online pricing on the tours we offer.

For price matching call

*Current Parasailing price on Carnival of $89.99 vs $39.95 with us

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Catamaran Champagne Sunset Sail

Sunset Sails
Parasailing
Key West Private Charters

Sunset in style. Join us for our exceptional Catamaran Champagne Sunset Sail

Key West is known for its world famous sunsets. The local way to experience one is with Sebago. Let us make your Key West vacation complete with a sunset sail on Sebago Flyer or Sebago Cubed, our 60′ sailing catamarans with plenty of room to stretch out and enjoy the breathtaking view.

Enjoy drinks throughout the tour with complimentary champagne, wine, sangria chilled beers and soft drinks.

After leaving Key West’s Historic Seaport, sails are raised to provide you with a brisk, true sailing experience. During your Key West catamaran cruise, feel the wind in your hair and the ocean breeze caress your skin. Take in Key West landmarks like the Mallory Square Sunset celebration, Sunset Key and historic Fort Zachary Taylor.

As the sun starts its descent, your experienced Sebago captain carefully positions the boat for the best view of Key West’s spectacular sunset. As the sun slides beneath the western horizon, steal a kiss from your loved one. Gather your friends and family around you as the painted sky fades to dark and the starlit sky puts on its own show. What a perfect ending to your day in paradise!

Catamaran Champagne Sunset Sail 2.5 – Hour Sail Summer: 6:00pm – 8:30pm (boarding starts 1/2 hour prior) Winter: 4:30pm – 7:00pm (boarding starts 1/2 hour prior)

YOU WILL BE SAILING ON ONE OF SEBAGO'S 60' CATAMARANS INCLUDED SEBAGO FLYER OR SEBAGO CUBED CATAMARAN FEATURING:

Plenty of seating, both in the sun and shade

Limited number of passengers below capacity so you have room to spread out

Spacious heads (bathrooms)

WHAT TO BRING

Grab your hat, sunglasses, camera and love of adventure. We will do the rest! Please bring a valid, government issued photo ID. Some activities and enjoying alcoholic beverages require that we verify your age.

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Parasailing – Key West

$69.95 Regularly $89.95

Every Hour on the Hour

9:00AM to 5:00PM

Key West Reef Snorkel – Morning

$49.95 Regularly $59.95

SUMMER: 6:00PM WINTER: 4:30PM

Boarding starts 1/2 hour before. Spring and Fall times vary by the sunset – please check your booking confirmation for exact departure times. Please bring a valid, government issued photo ID. Some activities and enjoying alcoholic beverages require that we verify your age. All prices do not include Florida sales tax.

Tour Includes:

Sail Past Local Landmarks as you Enjoy a Famous Key West Sunset
Champagne, Sangria, Wine, Beer, Soft Drinks and Filtered Water
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The 13 Best Key West Tours

Explore everything from busy streets to tranquil waters on one of these guided adventures.

Courtesy of Fury Water Adventures

Hop on Fury Water Adventures' boat to see local wildlife both from the boat and in the water.

When you imagine a vacation to Key West, Florida , you'll likely think of days spent on white beaches surrounded by turquoise waters and swaying palm trees. While lounging on the sand is an excellent option, there are also plenty of outdoor activities, attractions and culinary delights to keep you entertained while visiting the southernmost point in the country. U.S. News consulted both traveler reviews and expert opinion to compile this list of the best Key West tours.

Note: Some tour providers on this list may be running more limited operations due to COVID-19 or may impose testing or vaccine requirements. Check with your tour operator about availability before you book.

Fury Water Adventures Key West – Key West Dolphin Watch and Snorkel Tour

Fury Water Adventures' three-hour tour combines two popular Florida activities. First, watch Atlantic bottlenose dolphins as they playfully swim near the catamaran. Then, snorkel in the clear, turquoise waters of Key West, keeping your eyes peeled for stingrays, tropical fish and a variety of coral. Reviews are mostly positive for the dolphin watching portion of the trip, but travelers are less impressed with the snorkeling. Some tourgoers say the reefs aren't colorful and report seeing few fish.

Departures are at 10 a.m. and 2 p.m. from September through March. From March through August, trips leave at 9 a.m. as well as 12:30 and 5 p.m. Tickets cost approximately $70 for participants ages 11 and older and $55 for children ages 4 to 10. Children 3 and younger can participate for free, but do need a ticket. Tickets include beverages; beer and wine will be served after snorkeling. Fury Water Adventures also operates sunset cruises and parasailing adventures, among other options.

[ View & Book Tickets .]

Key West Eco Tours – Backcountry Kayak & Paddleboard Tour

Paddle through mangroves as you learn about the marine life and tropical ecosystem of the Florida Keys on this guided kayak or paddleboard tour, which begins just a short drive from downtown Key West in Geiger Key. Opportunities for wildlife viewing include turtles, dolphins, iguanas and rays, as well as birds and fish. Tourgoers remark that the experience provides a nice break from the city and offers a different perspective of Key West. They also say the guides are very knowledgeable about local marine life.

Two-hour tours operate at 9 a.m., noon and 3 p.m. every day. Paddleboards are an option for participants ages 13 and older. Prices start at $65 for adults and $50 for children 12 and younger. The company also provides a complimentary shuttle to and from Key West hotels . Half-day tours and sunset sails are also available.

Key Lime Bike Tours

Take in the colorful sights and sounds of Old Town with this approximately three-hour bicycle tour. You'll ride around town on a bright green bike (complete with a basket for personal items) and receive a complimentary piece of Key lime pie at the end of the tour. Reviewers applaud the entertaining and informative guides, who they say pack a lot of history into a relatively short ride. They also describe the cycling pace as leisurely and manageable for most fitness levels.

Tours are offered daily at 10 a.m. year-round. Prices start at $45 per person and include a helmet and bottled water.

Key West Ghost & Mysteries Tour

As one of Florida's oldest cities, it's not surprising that ghosts could be lurking in Key West's streets. This spooky 90-minute walking tour departs nightly at 9 p.m. and explores the haunted parts of town that most visitors don't see. Among the stops featured are Key West's oldest graveyard and Hemingway's first home, Casa Antigua. Tourgoers say that overall the stories are entertaining, though not particularly spine-chilling.

Prices start at $23 for adults and $15 for children ages 6 to 12; discounts are available for members of the military.

Key West Food Tours – Southernmost Food Tasting & Cultural Walking Tour

Visitors say the food sampled on this excursion is delicious and that the trip is the perfect introduction to Key West's culinary scene. The three-hour tour spotlights the Cuban and Caribbean influence on the city's food and culture. Samples could include fish tacos, Cuban roast pork, conch fritters, and of course, a rum drink and Key lime pie. The tour narrative also includes local history and fun facts about Key West, which tourists appreciate. The walking tour covers almost 1 1/2 miles with stops at five different venues.

Prices start at $75 for adults and $49 for children ages 5 to 12; kids younger than 5 can join for free. Tours operate daily at 11 a.m. and 3:30 p.m., though additional tour times may be added. In addition to food tours, the company hosts a Key West bar crawl for cocktail enthusiasts.

[View & Book Tickets: Option 1 | Option 2 | Option 3 .]

Danger Charters – Wind & Wine Sunset Sail

Climb aboard Danger Charters' 65-foot schooner for the company's nightly Wind & Wine Sunset Sail. The two-hour cruise features tropical music, a selection of hors d'oeuvres, and a variety of wines and beers to choose from. Plus, tours are capped at 25 participants – a highlight for reviewers, who appreciate the small-group feel. Visitors enjoy the sunset views, beverages and bites. They also suggest bringing a jacket as it gets cool once the sun goes down.

Tours depart daily at 4:30, 6 or 6:30 p.m., depending on the time of year. Prices start at approximately $110 for participants ages 13 and older. The company also offers a full-day sail, kayak and snorkel tour.

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Visiting the Southernmost Point is a highlight for many travelers' trips to Key West.

Old Town Trolley Tours – 1-Day Key West Tour

Ditch the car and hop on this narrated trolley tour, which features 13 stops at popular Key West attractions. At any stop, visitors are welcome to get off the trolley to explore and hop back on at a later time to continue the tour. Highlights include Mallory Square , Duval Street, the Southernmost Point buoy and the Harry S. Truman Little White House . Travelers enjoy the informative drivers and say the tour is a good value. They also appreciate the convenience of the trolley and say this is a great activity for your first day in Key West. Others note there are long wait times for trolleys and crowded vehicles. Without hopping off, tours last approximately 90 minutes.

Tours operate daily from 10 a.m. to 4:30 p.m. Tickets cost approximately $60 for adults and $25 for children ages 4 to 12 for one-day, unlimited hop-on, hop-off rides. Tickets also include complimentary admission to the Sails to Rails Museum. Two-day tickets are also available, along with a nighttime Ghosts & Gravestones Tour.

Lazy Dog Adventures – Key West Kayak Eco-Tour

Lazy Dog Adventures' guided mangrove tour begins 4 miles from downtown Key West on Stock Island. The slow-paced excursion is ideal for beginners and paddlers of all ages, and you can even bring your pup. During the two-hour tour, guides share information about the geology and animal inhabitants of the Florida Keys. Marine life sightings may include jellyfish, crabs, sea stars and tropical fish, as well as aquatic birds. Tourgoers appreciate the casual pace of the tour and find it both educational and fascinating to see the wildlife up-close. Some reviewers call it the highlight of their trip.

Tours begin at 10 a.m. and 2 p.m. daily. Prices start at $55 for adults and $30 for children 11 and younger; discounts are available for locals and members of the military. Lazy Dog Adventures also offers paddleboard and eco-boating excursions.

Conch Tour Train

A staple in Key West since 1958, the open-air Conch Tour Train makes three stops along a narrated, 75-minute route. The first stop lets patrons off at Truval Village near the Key West Lighthouse and the Key West Butterfly & Nature Conservatory . The second stop is the Historic Key West Seaport and the final stop is the Sails to Rails Museum, where train passengers can take advantage of complimentary admission. Along the way, passengers can disembark and explore Key West attractions before catching the next train. Visitors give mostly positive reviews of the conductors' knowledge and remark that the train ride offers a great way to get an overview of Key West in a short amount of time.

Ticket prices for single-day passes cost approximately $50 for adults and $25 for kids ages 4 to 12; children 3 and younger ride free. Discounted tickets are available if purchased online. Two-day passes are also available. The train operates daily from 10:15 a.m. to 4:15 p.m.

Sebago Watersports – Key West Reef Snorkel - Morning

This morning snorkel begins with a 7-mile sail to the Florida Reef, the only living coral barrier reef in the U.S. Enjoy the warm ocean breezes as you cruise on the company's 69-foot catamaran. Then, view tropical fish, turtles and lobsters as you snorkel in the crystal-clear Caribbean waters. Visitors commend the crew's professionalism and the enjoyable catamaran ride. They also report seeing a variety of fish and marine life.

The three-hour tour begins at 9 a.m. daily and includes snorkel gear and instruction. Complimentary soft drinks, water, and wine and beer (available after snorkeling) are also included. Tickets start at $40 for adults and $35 for children ages 4 to 11. Sebago Watersports also operates catamaran sunset sails, among other tours.

Key West Extreme Adventures – Shark and Wildlife Tour

If you're hoping to see sharks in the wild, consider this two-hour catamaran tour with Key West Extreme Adventures. You'll cruise a few miles off the coast keeping your eyes peeled for dolphins, stingrays, turtles and birds before the captain drops bait into the waters to attract lemon and nurse sharks to the boat. Tourgoers praise the knowledgeable captain and crew and report seeing a plethora of sharks.

Tours generally depart Thursday through Tuesday at 10 a.m., though they may be available daily, depending on the month. Tickets cost approximately $90 for adults and around $50 for kids ages 6 to 16. Children 5 and younger can ride for free.

Catamaran Echo – Adults only Champagne Celebration Sunset Cruise from Key West

Reviewers regularly call this two-hour sunset cruise relaxing and lovely. This adults-only tour includes unlimited Champagne, as well as red and white wine, beer, soft drinks, water and a cheese buffet. Though the catamaran can accommodate up to 28 passengers, capacity is capped at 14 people to create an intimate atmosphere – another highlight for tourgoers.

Cruises are available daily; departure times vary by season. In the summer months, the tour departs at 6:30 p.m. In the winter, the boat departs at 4 p.m. Tickets cost approximately $75 per person and include all beverages and food. All ages are welcome on private sunset charters, as well as the company's dolphin and snorkeling tour.

Honest Eco – Dolphin Watch & Snorkel

Eco-conscious travelers may want to book this four-hour tour, which takes places on a custom-built electric catamaran. Along with the hybrid boat, the tour is led by marine biologists. Reviewers praise the guides for their vast knowledge of the animals and ecosystem and also appreciate that the electric boat doesn't scare off dolphins thanks to its quiet motor. During the four-hour excursion, you'll watch dolphins swim alongside the boat, and then get a chance to snorkel with a member of the crew as your guide. According to the company, this tour is suitable for novice and beginner snorkelers.

Tours are available daily at 9 a.m. and 2 p.m. Tickets cost approximately $110 for adults and around $90 for children ages 2 to 11. Honest Eco also runs a sunset sail, among other options.

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Key West Catamaran Sail and Snorkel
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Luxury Sailboat Rental Key West, FL
10 Best Boat Tours In Key West, Florida
Sunset Sail Key West
Luxury Sailboat Rental Key West, FL

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THE TOP 10 Key West Sailing Tours (w/Prices)
Key West Small-Group Sunset Sail with Wine. 994. Escape to the still waters off the coast of Key West on this small-group, sunset wine-tasting cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a 65-foot schooner. Sample up to eight different wines and/or five different beers.
Key West Sunset Cruise, Sunset Sail, Day Sailing & Private Yacht Charters
Key West Sunset Cruise, Day Sail, Sunset Sail, Sightseeing Sailing Boat Tours, Private Yacht Charters on Schooner America 2.0 | Classic Harbor Line. Toggle navigation. Classic Harbor Line. Home 305-293-7245 Key West, FL ... Afternoon Key West day sail, Full Moon, Star-Gazer Sails; ...
THE 10 BEST Key West Boat Tours (Updated 2024)
Filters • 1. Sort. Mallory Square. Key West Historic Seaport. Fort Zachary Taylor Historic State Park. Sebago Key West. Top Key West Boat Tours: See reviews and photos of Boat Tours in Key West, Florida on Tripadvisor.
Sunset Sail Key West
Welcome to Sunset Sail Key West, Key West's most versatile custom charter experience. With three beautiful vintage boats, great local captains and crew, and the pristine waters of the Florida Keys at our disposal, we're confident that we'll have everything you need to make your dream sail come true. (305) 587-4488.
THE TOP 10 Key West Boat Cruises, Sailing & Water Tours (w/Prices)
Key West Mangrove Kayak Eco Tour. 1,577. Paddle a kayak through mangrove creeks and shallow water on a Key West kayaking tour that offers an up-close look that this unique coastal environment. This guided tour is the perfect way to spot Florida wildlife in a natural habitat.
Key West Sailing Adventure and Sunset Sails
A Key West sailing adventure aboard the Schooner Jolly II Rover takes you back in time on a classic 80' tall ship to an era of pirates, rum runners and privateers seeking freedom and solitude. Their spirit of independence lives on daily on the Jolly II Rover. Roling Thunder Happy Hour from James Papagno on Vimeo.
Key West Sunset Sail Aboard Schooner America 2.0 2024
Overview. Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand Key Light Tower and more. Enjoy complimentary beverages throughout your sail along with individually plated ...
Danger Charters
Locally owned and operated for more than 30 years, Danger Charters is all about the Key West sailing experience - wind in the sails, sun on our face, the sound of the waves lapping against the hull. Our shallow-draft schooners allow us to go where others can't … and we choose to go where others don't. We seek calm, crystal-clear water ...
Key West Sailing Adventure
Sailing and snorkeling is the best fun Key West has to offer. Choose a sailboat to truly enjoy the Key West experience. Our captains will sail you to the barrier reef to snorkel, take in a sunset, dive a wreck, fishing is an option, visit the dolphin playground. See the beauty this paradise has to offer. One of the favorite charters is the 24 ...
Key West Sailing Charters with Argo Navis
Hindu Charters is a family-owned, local business sailing out of both Key West, Florida and Provincetown, Massachusetts. Schooner Hindu, one of the oldest, most historic wooden schooners in the Florida Keys, has been sailing out of P-Town since 1946. Built in 1925, Hindu is undergoing a top to bottom historic restoration just in time for her 100 ...
Key West Sailing Charters
Our Key West sailing charter destination is located minutes from all the downtown Key West attractions and Duval Street night life, yet a short sail away from pristine reefs, underwater nature preserves, and uninhabited island locations such as the stunning and secluded Marquesas. Kayak, paddle board, and snorkeling excursions will open to you ...
Key West Award Winning Schooner Sailing Cruises
Choose from our award winning Key West Sunset Sail, Key West Windjammer Day Sail, Key West Eco-Tour or start your vacation with our Key West Bloody Mary Sail. Learn More. Discover These Great Key West Wooden Schooners. Step aboard the Appledore II for a true sailing adventure. This two-masted hand-built wooden schooner calls both Camden, Maine ...
THE TOP 10 Key West Sunset Cruises (UPDATED 2024)
Key West Small-Group Sunset Sail with Wine. 992. Escape to the still waters off the coast of Key West on this small-group, sunset wine-tasting cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a 65-foot schooner. Sample up to eight different wines and/or five different beers.
The Best Key West Sunset Cruises (w/Prices & Reviews)
A Key West sunset cruise is a vacation must-do that adds an unforgettable experience to any Key West visit. Choose a graceful sailing schooner, a sleek modern catamaran, or a roomy dinner cruise liner with live music and all the trimmings - this curated selection of the best Key West sunset cruises offers good times set against one of nature's grandest spectacles.
7 Incredible Key West Boat Tours
Private boat tours in the heart of paradise. Key West Boat Trips offers the perfect launch pad for your next Key West vacation. Leave the crowds behind and enjoy a day out on one of our tour boats or spend an evening kayaking the mangroves. Choose from snorkeling, swimming, sandbar hopping, or even a sunset dinner cruise!
Key West Sunset, Snorkeling & Dinner Cruises
This is your chance to ride in the parade. Includes draft beer, wine, champagne, appetizers & live DJ. Learn More. From $89.95. Check Availability. Spend a day on the water with a Key West boat tour! Enjoy a sail with your loved ones, experience a world-famous sunset & groove to live music! Book now.
Key West Sunset Cruises & Sunset Sails
202 Williams Street Key West FL 33040. 3055874488 Email Website. Sit back, relax and toast the sunset on your own private charter on the "High Tide" or step back in time aboard the historic schooner "When And If" built for General George Patton to sail around the world in 1939. Allow us make your ideal sail come true!
Key West Sightseeing Boat Tour aboard Schooner America 2.0
Sit back and relax while Schooner America 2.0 plies effortlessly through the turquoise green Key West sailing waters and off towards the horizon for the quintessential Key West Sunset experience! (Call us directly to save 6% online processing fee) Duration: 2 hrs Boat: America 2.0 Cost: Adult $104 | Child $36. BUY TICKETS NOW.
Sebago Watersports
Sebago Watersports is Key West's favorite choice for watersports. Amazing catamaran and schooner sunset and daytime sailing tours. Choose from sunset sails, parasailing, jet skis, snorkeling, eco tours and more. Book 7+ days in advance and receive an additional 5% off your online booking. Enter promo code EARLY at checkout.
Key West Sailing Tours
Explore the shallows of the Key West National Wildlife refuge aboard a beautiful sailing vessel. This boat features a combination of snorkeling, a fabulous lunch, kayaking the remote islands of the keys, and relaxing on remote private sandbars. Adult $ 134 00. Child (4 - 12) $ 109 00.
Catamaran Champagne Sunset Sail
3 Hours. DEPARTS DAILY: 9am. Book Now LEARN MORE. Sail Past Local Landmarks as you Enjoy a Famous Key West Sunset. Champagne, Sangria, Wine, Beer, Soft Drinks and Filtered Water. Experience Key West's famous sunset from the deck of Sebago's spacious sail cat. Key West's best sunset cruise is an amazing value that includes complimentary drinks.
The 13 Best Key West Tours
June 8, 2022, at 9:00 a.m. The 13 Best Key West Tours. Courtesy of Fury Water Adventures. Hop on Fury Water Adventures' boat to see local wildlife both from the boat and in the water. When you ...
Key West: Sunset Sail On The Schooner 'when And If'
Sail away on this magnificent ship with other guests on a shared experience: A Key West must-do - a 2 hour sunset sail. Book your spots early to avoid disappointment! - With room for up to 28 people to enjoy the gorgeous Key West sunset, the antique schooner yacht provides smooth sailing and a cool ocean breeze.