sailboat rental annapolis

Rainbow 24 Sailboat Rental

No trip to the sailing capital of America would be complete without getting out on a sailboat. Our fleet of Rainbow 24s provides a safe and fun experience for those looking to have a relaxing time on the water. Feel free to bring lunch and turn it into a picnic as you pass by the sights with the wind carrying you along.

Rentals are available during our sailing season, from the beginning of April to the end of October.

Weekdays – $158 (+taxes and fees) for a full day or any portion of a day between 9 am – 4 pm.

Weekends & Holidays – $225 (+taxes and fees) for a half-day between 9 am – 12:00 pm OR 1:00 pm – 4:00 pm

*If you are a new customer, you are required to complete a 30-minute sailing assessment. The assessment cost $30 in addition to the rental fee.

Reservations

A reservation is needed to ensure that a sailboat is available when you want to go out. At least two adults are required on a rental boat, one of whom must be a qualified sailor. Up to 6 people are permitted on a rental boat; no children under 5 years of age are allowed. No pets are permitted.

A late fee of $75 will be charged per every half-hour overdue.

To reserve a Rainbow Rental, please call 410.267.7205 or email   [email protected]

KeelBoat Club Members: Click the button below to jump to the KeelBoat Club Rainbow Rental’s page. You can also click on the “KeelBoat Club” tab and visit the drop-down labeled “KeelBoat Club Rentals”. Please have your membership ID ready.

KeelBoat Club Rainbow Rentals

Our Rainbow 24 sloops have proven to be nimble, fast, and forgiving. Designed by Sparkman and Stephens specifically for Annapolis Sailing School, the boats are ready to please both novice and experienced sailors. The substantial fixed keel (1100 lbs), cuddy cabin design, and large cockpit combine to produce a boat that is stable, dry, and comfortable.

Qualified Renters

At least one person in the rental party needs to have an ASA 101 certification or its equivalent. New customers must complete a sailing competency evaluation with us prior to their first rental. Renters are required to rig and de-rig their boat. The Rainbows do not have engines, so sailors must be able to depart and dock under sail.

If you need a refresher on rolling and flaking our sails, check out our how-to page here !

Sailing Area

Rentals are restricted to an area close enough to the school so that help can reach you quickly in an emergency situation. Boundaries, determined by management, are subject to change depending on weather and water conditions at the time of your rental. Please understand that going beyond these boundaries makes quick retrieval of the boats difficult in case of emergency. Late returns of boats due to venturing beyond the boundaries will result in late fees. If a renter goes outside the prescribed sailing area and needs to be retrieved, there will be a fee of $75 and the renter will be unable to rent with us in the future.

Sailing is entirely dependent upon wind and weather. We recommend that renters check marine.weather.gov three days before the rental date to see what the forecast is for that day. If small craft advisories or worse are in effect at the start of the rental, the rental may be postponed, canceled, or otherwise restricted at the discretion of the management. In that case, the rental can be re-booked at no additional cost. In low wind situations, you will need to plan your sail so that you can be back at the dock on time.

Cancellations

Rental reservations are charged at the time of booking. Rescheduling within three calendar days of the originally scheduled start of the reservation will result in a $50 rescheduling fee per occurrence. Cancellations made within two calendar days of the scheduled day of the reservation will receive no refund. Refunds are not available for lack of wind.

The boats are covered by insurance. Please inform management of any damage that occurred during the rental. The Lessee has no liability for repairs. However, Annapolis Sailing School is not responsible for personal injury or damage to other boats. You should check your own insurance coverage before sailing.

Other Restrictions

• Children on board must be at least 5 years old
• No alcohol allowed on boats
• No pets allowed on boats
• No swimming off the boats allowed
• No anchoring
• Boats are not permitted to dock at other marinas or facilities other than Annapolis Sailing School

Want to stay in the know about Annapolis Sailing School? Sign up for our new monthly newsletter here to receive information on classes, events, schedules and more!

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Find the best Annapolis, MD Boat Rentals and Yacht Charters Near You

• Boat Rentals
• Maryland Boat Rentals

Top Annapolis, MD Boat Rentals and Yacht Charters

Edgewater, MD

26’ Sea Fox w/ Restroom - Bachelor-ette Parties!!!

"Equinox" - Center of the Sun - Lippincott 30'

Annapolis, MD

Go Fishing, Cruising or Explore the Waters!

Pasadena, MD

Still Crazy II - Cruise the Chesapeake in luxury! (Captained)

Sailing Vessel (S/V) DreamCatcher

New Yacht Charter

Grasonville, MD

Fun 27' Bow Rider. Great for Water Tubing!

Glen Burnie, MD

Tahoe T16: Your Ticket to Fun on the Water!

20' Regal Great for cruising & relaxing

36' Mainship Sedan Bridge

29' Sea Ray Sundancer

2017 Bennington 20SL Pontoon for Annapolis sightseeing in style!

Chester, MD

Bayliner VR6 at Kent Narrows!

Chaparral 256 SSX

Stevensville, MD

Fishing in Chesapeake Bay with Capt. Jason Seman!

Stable, comfortable & fast - sleeps 8 w/4 baths!

Sailing Charter - Sunset Cruises, Learn to Sail, and Family Fun Time!

Experience sailing in the heart of Annapolis md

How to rent a boat in annapolis, find the perfect boat.

Enter your desired location and date to explore our fleet of boat, Annapolis, MD, United Statess.

Select a captain

Choose to drive yourself or select a USCG licensed captain.

Book with ease

Connect with your boat owner and complete your booking online.

Enjoy your day on the water with friends and family!

Why Boatsetter?

As the global leader in peer-to-peer boat rentals, Boatsetter offers an easy, safe and accessible way to experience on-the-water adventure. With boat rentals in 600+ locations, finding a boat is easy and with the option to tap into the largest network of USCG licensed captains, boating experience is not required.

Get out on the water worry-free, knowing our insurance covers every boating trip

Choosing the right boat rental platform is essential to your peace of mind while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

Got questions?

Frequently asked questions

What makes Boatsetter different from other boat rental platforms?

What makes Boatsetter different is peace of mind. Boatsetter is the first and only boat rental marketplace to offer insurance on every peer-to-peer boat rental. We know choosing the right boat rental platform is essential to your experience while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

How to rent a boat on Boatsetter?

At Boatsetter, our mission is to make getting out on the water as easy as possible. With our intuitive booking system, you can rent a boat as soon as today. -First, you must determine your budget and the type of boat you want to rent. -Next, decide where you would like to boat and the kind of boat you would like to spend the day on. -Finally, determine if you will be needing a boat captain and reach out to the boat owner. That’s it! You’re officially on your way to a fantastic day out on the water.

How much does it cost to rent a boat?

The cost to rent a boat depends on whether you are renting for a half-day or a full day, the boat features and the boat size can impact your boat rental price. Rental prices can range from $200 to $1,000 plus depending on the boat rental itself and the length of time of the rental.

How many people can fit on the boat rental?

The number of people who can fit on boat rental largely depends on the boat’s size and how many life jackets are on board. Currently the coast guard allows a maximum of 10-12 people on a Boatsetter boat rental.

How much does it cost to rent a yacht?

The cost of renting a yacht depends on the boat’s size and the amount of time you’ll use the yacht. The onboard amenities and luxurious accommodations also dictate the price. You can contact our yacht specialists for a custom quote by visiting https://www.boatsetter.com/luxury-yacht-charters .

How old do you have to be to rent a boat?

You must be 18 years old to rent a captained boat and 25 years old if you would like to rent a bareboat charter.

Do I need a boating license to rent a boat?

Boating license requirements vary from state to state. As a renter, you are responsible for understanding local state requirements.

Can you rent a yacht for the day?

Boatsetter allows you to rent a yacht for the day. Single-day yacht rentals are available for a select number of yachts. To chat with a yacht specialist please visit https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the week?

Boatsetter allows its customers to rent a yacht for the week. Renting a yacht for a week gives you more access to the wide range of yachts available on our platform. You can either book a rental directly through the site or connect with one of our charter specialists to plan your trip here: https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the month?

Booking a month-long yacht rental is a detailed and hands-off process when working with our team of yacht charter specialists. We tailor each yacht charter to our client's specific wants and needs. Our luxury yacht charter specialists can be reached at (954) 715-4114 or by visiting https://www.boatsetter.com/luxury-yacht-charters .

How to rent a private yacht?

Renting a private yacht is a very detailed experience that caters to your exact needs while onboard one of our luxury yachts. To plan your private yacht rentals experience please visit https://www.boatsetter.com/luxury-yacht-charters .

How much does it cost to rent a pontoon boat?

The cost of renting a pontoon boat depends on the size, location, and rental time of the boat. Prices can range anywhere from $200 for a half-day rental or just under a $1,000 for longer rentals.

How much does it cost to charter a yacht?

The cost to charter a yacht varies depending on the boat size and the length of the charter. Prices typically range from less than $1,000 to $5,000 plus if you’re wanting to charter the yacht overnight.

How much does it cost to rent a boat for the day?

The cost of renting a boat for the day on average ranges from $200 to $1200. The cost to rent a boat varies depending on the size of the boat and the length of time that you will be using the boat.

How does the boat insurance work?

Boat insurance typically covers loss caused by things such as fire, sinking, storms, and collisions. The extent of the coverage varies depending on the policy.

Do I need my own insurance to rent a boat?

You do not need boat insurance when renting with Boatsetter. Coverage is provided under the Peer-to-Peer Boat Rental Policy, which is underwritten by GEICO Marine Insurance Company. The policy was written from the ground up as a stand-alone recreational boat rental insurance policy covering the period of time that the boat is being rented and is available for all non-commercially insured boats.

Does Boatsetter screen renters?

Yes. We use a system called Cognito to ensure that payment information matches the renter's identity. We also require renters taking out a captained boat to be at least 18 years old and on a bareboat to be at least 25 years old.

Is listing my boat on Boatsetter free?

Yes! Listing a boat is completely free. We only take a commission when your boat is rented. We only make money when you do!

What if I'm not comfortable having a renter drive my boat?

If you are not comfortable having a renter drive your boat, we have an expansive network of licensed and experienced captains. Once your boat is listed, you can filter through our network of captains and favorite captains in your area that you would like to operate your boat.

Top destinations for boat rentals, Annapolis, MD, United States

Browse by make

Annapolis’ Most Popular Experiences

Given its history, you will soon begin to understand why Annapolis is the perfect place to sail. Here are a few of the things you can get up to by the water. Join the fun at the Sailing Races In the summer months, all of the action can be found at the weekly Wednesday sailing race. You can either spectate from the side or follow the action from aboard your Annapolis boat rental. Get down to the Boat Shows In the spring and fall months, you can check out the U.S.’s oldest boat shows. Spectators flock in their tens of thousands to check out what’s been shown. Take a wander around and think about what type of Annapolis boat rental you’ll be taking out the next morning. Make Sure you Pack your Rod Fishing is a must when out on the water in Annapolis. You’re bound to fill your bags with the likes of Redfish, black drum, spotted seatrout, as well as both smallmouth and largemouth bass.

Annapolis’ Best Bodies of Water

Enjoy the Severn River

The Severn River is a quiet body of water that makes for the ultimate place to unwind on your Annapolis boat rental. It’s home to a restored oyster reef which gives it an abundance of marine life, so have your rod at the ready.

Loop Around Kent Island

You’ll see Kent Island directly opposite the shoreline at Annapolis. Take your Annapolis boat rental around for a casual loop of the island and take in its sights. Given its size, it’s likely to be the first destination on your mind.

Sail Down South River

South River offers a pleasant place to explore in Annapolis. Its tranquil waters create a relaxing and peaceful aura whereby you can only hear your boat skim across the water. Once you reach this body of water, all of your worries will pass away.

Top boat rental reviews in Annapolis, MD

Experience...

Boat was in excellent condition.

Still Crazy II -...

Such a great experience. The boat was perfect for our days on the water and the crew was very accommodating and...

"Equinox" -...

The boat is not large, but it is well-crafted and sails beautifully. Rodrigo was friendly, responsive, and detailed....

Rodrigo does a great job explaining everything and makes the whole transaction seamless. Boat is in good shape and...

Go Fishing,...

Trevor was great and easy to work with. He provided, a quick and complete run down of the boat and how to operate...

The boat was incredible and Will was graceful and helpful. Indie was an incredible dockmaster. We would absolutely...

Sailing Charter -...

Captain Audrey was fantastic as was Garrett. A wonderful trip where we were allowed to sit back and relax or help &...

Rodrigo has a wonderful boat, and ensures that everything you need (or need to know) has been taken care of. We...

Incredibly gracious host, charming boat

Bayliner VR6 at...

We had a fabulous time! We will definitely rent this boat again!!

We had a wonderful day on the Bay with Tyler as our guide. He knew the best spots to go to hang out, tube and...

Boat rentals in Annapolis, MD

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The Best Sailboat Rentals in Annapolis

Browse, book, and get out onto the water with local captains and boat owners., our favorite sailboat rentals in annapolis.

5 (333 reviews)

• Boat Rentals

the United States

Experience the Serenity of Sailing SV Magic

50ft Catamaran Charter with Water Toys - Annapolis, MD

38-ft Hunter 376 Sailing Adventure in Annapolis

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

Charter 44' Orana Cruising Catamaran In Deale, Maryland

Charter 42' Lagoon Catamaran in Annapolis, MD

50ft Catamaran Charter with Water Toys in St. Michaels, MD

Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

43foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

Suggested searches, types of boats popular in annapolis.

From mid-size to mega yachts, these luxury boats are great for groups and celebrations

$250-$2,075

Explore local waters with a boat rental dedicated to sightseeing and exploration

Perfect for casual cruising, sandbar stops, swimming, and parties

Fishing Boats

Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts

All the comforts of home out on the water, for multi-day boat trips

Who says you need a motor to have fun on the water?

• Fishing Charters

Let a captain do the driving while you do the fishing

Top Sailboat Rental Locations Near Annapolis

Washington , District of Columbia

94 listings

Baltimore , Maryland

41 listings

Most Popular Yacht Rentals in Annapolis

43ft Cruiser Express Yacht for Daily Charter

Private Yacht Charter: On 40ft Regal Commodore

Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland

45' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 32 Guests Capacity

Most popular boat tours in annapolis.

Pristine Hooligan Departs from a Private Pier with a Captain and Fuel INCLUDED

Chaparral SSX 27ft - Captained Private Charter - Watersports Included!!

Relaxing Excitement of the Chesapeake Bay and tributaries on our Ocean Yacht

Still Crazy II - Cruise the Chesapeake in luxury! (Captain Included)

Most popular pontoon rentals in annapolis.

Sea Doo Switch - Sea Cruiser Pontoon in Pasadena MD

Bentley 220 Cruise Pontoon for rent in Edgewater

30' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 6 Guests Capacity

Recent reviews in annapolis.

Our family of four, who are experienced sailors, appreciated the opportunity to sail with Alberto and his lovely wife, who shared lots of great stories and reflections of sailing on the Bay. The boat was perfect for a day of sailing, and exactly how described on the website. It was clean and comfortable and we felt completely welcomed, and were able to participate in sailing activities as we desired, while also relaxing and enjoying some downtime. Great time sailing!

HIGHLY recommend Capt Joe for a fantastic sailing experience out of Rock Hall. Joe worked with us to get a last-minute booking when another booking fell through. He and his crew are experts and you will not be disappointed. He let us take the helm and participate as much or as little as we wanted to. Sol Searcher is a beautiful, well-equipped boat - plenty of comfort and speed (wind dependent of course.)

Captain Alberto and Grace were amazing, and helped with a very romantic sunset sail. The were ver gracious, accommodating, and knowledgeable. If we get the chance we will definitely come back and hire them again!

We rented Josh’s boat to do our engagement pictures! He was helpful with timing to catch the best sunset and navigated the boat so our photographer could get the best shots. There was room below for outfit changes and speakers on board to enjoy our time!

Had a fantastic day sailing with Josh! He was great with communications and was ready to go when we got there. The boat is very comfortable and while we only did a 3 hour sail, the boat has a good galley and bathroom and would be great for a longer sail. The marina location is excellent and we were in the Chesapeake in 15 to 20 minutes. Josh was a great captain - we enjoyed chatting with him and he made us very comfortable. Highly recommended.

We had an awesome trip with Josh. He was very flexible with timing and knowledgeable about sailing. We were able to take our engagement photos on Josh’s boat with his help and input on lighting/backgrounds. It was a wonderful experience we will never forget!

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How To Book on Getmyboat

Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.

Inquire & Book

Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.

Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!

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21 boat rentals in Annapolis, MD

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Rent a Boat Charter in Annapolis, Maryland with Sailo!

Looking for a boat rental Annapolis, MD? Let's start choosing the right private yacht rental in Annapolis, MD - the charming capital of Maryland — is quintessentially maritime. Home of the US Naval Academy, this amazing town preserves the authentic Colonial atmosphere: cobblestone streets, original lamp posts and brick row houses. Sailing is ingrained in Annapolis — a boat rental comes naturally if you choose to spend a few days around here.

How to rent a boat in Annapolis, Maryland?

Check out our extensive inventory and pick the yacht rental in Annapolis, MD that suits your plans for having fun on the water. Whether you are into watersports, looking for a relaxed cruise, or to go for a fishing trip, this famous boating destination has something for every taste. If you’re around for the 4th of July, you’ll get the chance to enjoy the amazing fireworks right from your boat!

A boat rental to Chesapeake bay is the perfect choice for a romantic sunset cruise to enjoy the scenic skyline, or a visit to the historic Kent island. There are many things to do by boat in “America’s Sailing Capital”. Browse, pick your Annapolis, MD boat rental and get ready for a memorable nautical adventure! We also invite you to check our top boat selections in other locations in Maryland: Pasadena boat charters and Solomons Island boat rentals .

Sailo concierge team is here to help you rent the perfect private boat charter in Annapolis to go sailing in Maryland. To ask for more details or request special arrangements on your private yacht rental in Annapolis, MD, please send a direct message to the boat representative, or reach out to us on live chat.

Annapolis, MD could be the ideal yachting playground for you

Boating in Annapolis is a thrilling experience and one best savoured with your own private yacht charter. Choose your perfect boat rental in Annapolis and step aboard with your family or friends for a spectacular day on the water. Escape the crowds and enjoy some of the most beautiful scenery in Maryland from the deck of your own yacht charter.

Top private boat rentals in Annapolis, MD

Want to rent a boat in Annapolis, MD? You’ll find 9 boats waiting for you to take them on an adventure here on Sailo. Choose from our sailboat rentals in Annapolis, MD . Another great choice is a catamaran rental in Annapolis, MD . Fans of luxury motor yachts will be spoiled for choice with our multiple motor yacht charters in Annapolis . Maryland is an excellent place to enjoy a party, so discover our party boat rentals in Annapolis, MD for 13+ guests in Annapolis and see for yourself.

How to find a boat charter in Annapolis, Maryland?

Choosing the perfect Sailo boat for you in Annapolis, MD is easy and quick thanks to our advanced filters! First we recommend filtering by date and trip duration. Whether you look for a 2, 4 hrs or a full day boat rental in Annapolis, MD, the group size is very important, as well as the type of boat you want for your adventure in the waters of Maryland. Use the price filter to see only options according to your budget and click on the 'Crew' button to choose if you want a Annapolis boat charter with a captain or you want to drive it yourself (option Bareboat). Once a Annapolis yacht charter catches your eye, click on it to see the boat page with more photos and a detailed description. Check the reviews and send a direct message to the boat owner to ask more details!

How much does it cost to rent a yacht charter in Annapolis, MD for a day?

Annapolis boat rentals prices vary significantly. You can find great budget friendly private yacht rentals in Annapolis, MD starting from $250 for a daily trip. Luxury or party yacht rentals for the day can cost up to $6500 where service fees and mandatory extras are not included. Your budget per day will vary depending on whether you are renting the boat in Annapolis with captain and/or crew, fuel cost, special requests for pick-up and drop-off or other special arrangements you may want to make with the owner.

Can I pay in installments for my Sailo Annapolis boat rental?

A lot of our boat owners allow payment in installments, particularly for the weekly yacht charters in Annapolis, MD. First installment is always charged at the time the booking is confirmed. To find out if a boat has an installment plan, reach out to the boat representative and ask details via 'Message Owner' before you submit the booking or check out the Payment Schedule at top of the booking page.

Responsible boating guidelines

• Take your rubbish home
• Use eco-friendly sunblock
• Avoid single use plastic

Popular locations to rent a boat in Maryland

• boat rental St Michaels, MD
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