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ISLAND WINDJAMMERS

Mar 8, 2021 | 0

ISLAND WINDJAMMERS

Island Windjammers

Remember Windjammer Barefoot Cruises? Enormously popular in the ‘80s and ‘90s for its ultra-casual, rum-fueled Caribbean sailing adventures, the line folded in 2008, leaving thousands of loyal passengers sad and landlocked. Enter Island Windjammers.

Launched in 2009 by and for Windjammer Barefoot regulars when they got together to buy the 101-foot brigantine schooner Diamant , the line is a more mature version of its barefoot predecessor, operating truly intimate sailing adventures that tootle around the quieter corners of the Caribbean, far from the megaship mega-crowds.

Sure, there’s still plenty of rum punch and Red Stripes consumed, but the volume of the party has been turned way down to just the perfect level. (Island Windjammers is not to be confused with Sail Windjammer, a now defunct one-ship line that used to operate the 72-pax Mandalay , formerly of the Windjammer Barefoot Cruises fleet.)

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Island Windjammers

Diamant in all her glory. * Photo: Island Windjammers

Diamant (built 1978 & 10 passengers) – Windward Islands, Caribbean

Vela (b. 1988 & 26 p) – British Virgin Islands, French West Indies & Leeward Islands, Caribbean

Note: the 24-passenger 1960-built Sagitta is no longer a part of the Island Windjammers fleet.

Island Windjammers has started offering yacht charters in Europe; they did Croatia in 2023 and in 2024, it’s the Greek Isles aboard the 8-pax Lyra doing 10-night itineraries. More info HERE.

Island Windjammers Passenger Profile

Young-at-heart mostly American couples, singles and groups of friends 45+ who crave a carefree Caribbean getaway with zero pretension.

Summers and holiday weeks see occasional families with children; though the minimum age is 8 and it’s probably better for kids to be at least 10 or 12+.

Note : Island Windjammer’s ships are not accessible for people with restricted mobility, as staircases are steep, doorways narrow and door sills high.

RELATED: Island Windjammers Reviews from Passengers.

Included Features

  • All on-board meals
  • Locally brewed beer, wine & rum punch*
  • Soft drinks & juice
  • Use of ship’s snorkel gear
  • Port taxes & government fees

*You’re also invited to bring along your own booze and the ships provide the mixers (there is no cash bar on board). Internet is not available, and some island locations will have to make do.

The fleet calls on great little places like Tobago Cays. * Photo: Island Windjammers

The fleet calls on great little places like Tobago Cays. * Photo: Island Windjammers

Island Windjammers Itineraries – Cruises Year-Round

  • 6- and 12-night Leeward Island cruises round-trip from St Martin or St. Lucia, calling on some combination of Anguilla, Antigua, Dominica (Portsmouth & Roseau), Guadeloupe, Iles des Saintes, Martinique, Montserrat, Nevis, St. Barths, St. Eustatius, St. Kitts, St. Lucia and Tintamarre
  • 6-, 9- and 12-night Windward Island cruises round-trip from Grenada or St. Lucia, calling on some combination of Bequia, Canouan, Carriacou (Tyrell Bay & Hillsborough), Grenada, Mayreau, Mustique, Petit St. Vincent, Sandy Island, St. Lucia, St Vincent, Tobago Cays, Union Island and Young Island
  • 6- and 12-night British Virgin Islands (BVIs) & Leeward Island cruises round-trip from St. Martin or Tortola, visiting some combination of Anguilla, Jost Van Dyke, Nevis, Norman Island, Salt Island, St. Barths, St. Kitts, St. Maarten, Tortola or Virgin Gorda
  • 6- and 12-night French West Indies cruises round-trip out of St. Lucia, visiting some combo of Dominica (Portsmouth & Roseau), Guadeloupe, Iles des Saintes, Martinique and St. Lucia

Sample Itinerary

In the British Virgin Islands, most 6-night cruises embark at Road Town on Tortola.

A typical round-trip itinerary will include calls at Cooper Island, Jost Van Dyke, Norman Islands and Virgin Gorda.

RELATED: A First Timer Falls in Love with Island Windjammers

Each day is more gorgeous than the last. * Photo: Island Windjammers

Each day is more gorgeous than the last. * Photo: Island Windjammers

To let your hair down, work on your tan and hang out with like-minded others who operate on island time.

When to Go?

All year around, though remember hurricane season in the Caribbean is officially June through November.

Activities & Entertainment

The day starts with the captain’s story time when he explains what’s happening for the day; the ships spend part of every day in port somewhere. The pace is easy going and free — while away the day swimming off the side of the ship (when conditions permit), take the ships’ kayaks for a spin nearby, try paddle boarding, or sip rum punch with new friends in an inflatable “floating island.”

There are a handful of shore excursions offered on most itineraries, but many passengers are content to find a good beach or wander around on their own. Sometimes lunch is served on a quiet beach somewhere, otherwise meals on are on board.

Occasionally passengers will arrange their own diving trips, and spend part of a day deep down under looking at the colorful fishies.

RELATED: Combining an Island Windjammers Cruise with Some Scuba Diving. by Elysa Leonard

Happy hour is a big thing and drinks on deck are a favored pastime for many; you’re free to bring aboard your favorite spirits or mixers, though why bother when beer, wine, rum punch and soft drinks are on the house.

Evenings, the crew may start a bonfire on a nearby beach or organize a pub-crawl.

Theme cruises from time to time focus on rum (with a rum expert on board to educate and do tastings), solo cruisers (no kids or couples allowed!), pirates (with costume contests, pirate trivia and visits to spots where Pirates of the Caribbean was filmed), local food tasting, and yoga. Om shanti! 🙏🏼

Island Windjammers

Swing from the rigging, yipeee! * Photo: Island Windjammers

Meals are served at one very social open seating at a few tables, with local dishes to the tune of chicken roti, conch soup, pumpkin soup, callaloo and fresh fish as well as continental standards the likes of cheeseburgers and salads.

Fresh island fruits are part of the picture, from passion fruit to guava, star fruit, sour oranges and bananas.

Vegetarian and Gluten Free diets are catered for but not Kosher nor Vegan.

The whole point of an Island Windjammer cruise is to be outside on deck soaking up the sun and fresh Caribbean air, and enjoying the sailing ship experience and the quirkiness of the vessels — each has a very interesting background. — Heidi Sarna

The 10-passenger Diamant was built in 1978 in Taiwan and then later spent two decades sailing in the Galapagos Islands before Island Windjammers purchased her in 2009. She’s been the fleet favorite ever since.

She got a facelift in fall 2016 that reduced her capacity to 10 passengers in five cabins and created an overall spiffier look (“sophisticated not stuffy” the line’s website points out).

Of the two passenger decks, the top deck has both covered and open-air dining tables, plus a bar and deck chairs. The cabins are on the lower deck; there’s no elevator

Diamant sports four cabins with double beds below and single bunk above, and with full bathrooms with separate showers; and a fifth cabin is a suite with a queen bed, sitting area and a full bathroom.

Small as you’d expect on sailing ships, but charming, wood-paneled and the perfect cozy nests to catch up your beauty rest; otherwise, life is lived up on deck or on shore.

All cabins have 110v outlets, blow dryers, shampoo/soap, portholes and private bathrooms with separate shower stall.

A cozy and very nautical Diamant cabin. * Photo: Island Windjammers

A cozy and very nautical Diamant cabin. * Photo: Island Windjammers

The 26-passenger Vela was built in 1988 in Puget Sound, Washington, and deployed in the Marshall Islands as a floating medical clinic called Tole Mour , or “Gift of Life and Health.” Later she was used as an education vessel for students studying sailing, oceanography and marine biology.

In late 2014, Island Windjammers purchased the ship and rechristened her Vela , and a year later did major renovations, replacing the dormitory-style cabins with en suite single and double cabins; there’s also a new pilot house, large enclosed bar and dining saloon on the top deck.

Vela ’ s cabins include two tiny Cadet Cabins with raised small double beds (for one or two people) each with a private all-in-one bathroom (no separate shower stall).

There are a pair of Solo Cabins, one with a porthole and one without, that share one bathroom with a separate shower stall (each cabin can accommodate one or two people).

The two Standard Cabins are a bit larger with a double lower bed and a single bunk above, while six Deluxe Cabins have a larger double bed with single bunk above.

A pair of Compass Cabins at the aft of the ship has a queen size bed (and no upper bunk) and the one and only Topsail Cabin has a queen bed and larger bathroom.

Finally, the relatively spacious Owner’s Suite has a king size bed, mini-fridges, and a large bathroom — both cabin and bathroom have portholes.

All cabins have 110v outlets, blow dryers, shampoo/soap, portholes, and all but two solo rooms, cabins have private bathrooms with showers.

Island Windjammers

Vela’s Owner’s Suite, not too shabby! * Photo: Island Windjammers

Along the Same Lines

Star Clippers is in the ballpark, though its passengers are more international and its ships are much larger, and the overall experience is more high-end. The Maine Windjammers — one of which is reviewed on QuirkyCruise.com, the J&E Riggin — have a similar vibe, though the Island Windjammers’ ships offer more of a “cruise” experience with more amenities.

Island Windjammers Contact

Georgia-based Island Windjammers ; 1-877-772-4549,

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© This article is protected by copyright, no part may be reproduced by any process without written permission from the author. All Rights Reserved. QuirkyCruise.com.

About The Author

QuirkyCruise

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Ted & Heidi are long-time travel writers with a penchant for small ship cruising. Between them they've traveled all over the world aboard hundreds and hundreds of small cruise ships of all kinds, from river boats to expedition vessels and sailing ships.

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Go Barefoot

Life can be stressful., going on vacation doesn’t have to be..

At Barefoot Cowboy, our team will help you personalize every part of your dream Caribbean getaway, so you can spend less time worrying and more time unwinding.

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With Barefoot Cowboy, You Can:

Escape on a charter that fits you, your party, and your preferences to a T

Make your vacation as lowkey or action-packed as you want it

Enjoy an itinerary that revolves around what you want to do, not the other way around

Have peace of mind knowing the crew is going above and beyond to keep you safe

Relax in a family-type atmosphere that’s friendly and private

Stop worrying about the little things and start making memories

Why Pay for a Vacation That Isn’t Any Fun?

Many charters, yachts, and cruises offer one-size-fits-all packages that don’t actually fit everyone. As a result, you could find yourself bored, overwhelmed, or stressed out—instead of relaxed and having a blast. At Barefoot Cowboy, we understand how frustrating it is to spend time and money planning the perfect voyage, only for the real thing to not live up to your expectations. That’s why we let you and up to 9 friends customize every part of your vacation. As an owner-operated (not crew ran) charter, Barefoot Cowboy ensures every part of your trip is 100% you, from activities to meals to destinations and much more. We’ll help you plan your dream voyage or bring your vision for a once-in-a-lifetime vacation to life, so you can kick off your shoes and truly unwind. Don’t miss out on the memories of a lifetime. Reach out to Barefoot Cowboy today and embark on a voyage you won’t stop talking about for years to come.

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What Other Voyagers Say...

To say this is a once in a lifetime vacation sounds cliché but it's just amazing. The crew, the food, the islands. Everything is top-notch.

Can’t wait to set sail again. This is so much more than a ‘cruise’ could ever offer.

- Jennifer Homer

barefoot sailboat cruises

It was all we dreamed it would be…Food was delicious and beautifully served…The staff exceptional. We’ll go every chance we get!!!

- Barbara Beasley

Beautiful boat with an outstanding crew! They know all of the best spots to visit around the VI, and all of the tips and tricks to make sure you get the most out of your vacation. It’s like having your own local guides as your hosts

- Kyler Rucker

3 Steps to an Unforgettable,

Stress-free adventure.

o say this is a once in a lifetime vacation sounds cliche but it's just amazing. The crew, the food, the islands. Everything is top-notch.

- Kyle Rucker

1. Reach out to Barefoot Cowboy

Give us a call or send us an email, and we’ll get back to you right away to talk through your ideal getaway and book your trip

2. Build your perfect vacation

Use our personalization sheet to pick every part of your one-of-a-kind charter voyage, from the destination and activities to meals and drink selection

3. Experience the voyage of a lifetime

Unwind, kick up your feet, and lose yourself in memories you’ll treasure for a lifetime and a vacation you’ll never want to end.

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Build Your Dream Caribbean Escape

With our charter preference sheet.

Do you want to travel to gorgeous destinations? Sample the best local cuisine? Or just lounge on the deck, soaking in the sun? Download the Barefoot Cowboy Preference Sheet to personalize every aspect of your dream vacation, including:

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Food, drinks, and restaurants

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Fun activities based on your activity level

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How early you want to get up and how late you’ll stay up

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Special accomodations like diet restrictions or health conditions

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And much more

Download this sheet as a guide to plan any tropical charter getaway.

To get your copy, simply fill out the form on this page..

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GO BAREFOOT!

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Bareboat Sailing Charters

AVAILABLE CHARTERS

Now taking reservations for May, June, July, August, Sept. & Oct. 2024 charters.

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Early May, late-Sept. & Oct. weekend or mid-week special 2-day rate starting from $1,750. Additional days can be added at $500 per day during early May, late-Sept. & Oct.

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Island Windjammer Cruises

PLANNING and SAILING made easy!

Whether you’re in the planning stages or already booked your adventure, we want to make things as easy as possible. You have questions, we have answers:

Take a look at the PLANNING GUIDE for: Airport codes, Arrival and Departure info and how to book your cruise.

Your SAILING GUIDE answers questions about: What to pack, WIFI, local currency, and tipping.

If you have questions not covered here, give us a call at 877.772.4549. We’re always standing by to assist!

See you on deck!

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Pre-Cruise Planning Guide

We want to make it easy for you to plan your sailing adventure. You have questions, we have answers. Here, you’ll find everything you need to know before you book your cruise. From airport codes, to when you need to be there and when to disembark — not that you’re going to want to! Let’s get started!

AIRPORT CODES

When should i fly in.

Plan to arrive at least one day prior to boarding.

WHAT TIME DO WE BOARD?

Grenada:   12:30 PM Dominica | Greece | St. Kitts | St. Lucia | St. Maarten | St. Vincent | Tortola:   2:00 PM Turks and Caicos (Providenciales) - 3:00 PM

Those affected by changes to boarding information will be contacted via email.

HOW DO I GET TO THE SHIP ON BOARDING DAY?

It's a breeze to make your own way to the ship on boarding day! Taxis are readily available at hotels and guest houses. Check here for recommended transfer companies in some ports.

American, Caribbean Air, United

Air Canada, American Airlines, British Airways, Caribbean Airlines, Condor, Delta, LIAT, Virgin Atlantic

Sky Express, Aegean Air, and Olympic from Athens

American Airlines, Air Canada, Air France, British Airways, Caribbean Airlines, Delta, Jet Blue, Liat, Qantas Airways, Seaborne Airline, United Airways, WestJet, Windward Island Airways International

Air Caribe, Air Martinique, American Airlines, American Eagle, Air Canada, British Airways, Condor, Delta, JetBlue, LIAT, United, US Air, Virgin Atlantic, West Jet

Tip: The international airport in St. Lucia is 1.5 - 2 hours from our ship's anchorages.

ST. MAARTEN

Air France, American Airlines, Air Canada, Air Transat, Caribbean Airlines, Condor, Delta, KLM, LIAT, Jet Blue, Sky Service, Sun Country, Spirit, United, US Air, West Jet

ST. VINCENT

American Airlines, Air Canada, Caribbean Airlines

Tortola has a small airport on Beef Island. Most flights are through San Juan, Puerto Rico, or St. Thomas offered by Cape Air, Seaborne, and Air Sunshine with occasional service by other airlines and charter flights.

TURKS AND CAICOS (PROVIDENCIALES)

Air Canada, American, Bahamasair, British Airways, Delta, SouthWest, United

WHAT TIME DO WE LEAVE THE SHIP ON DISEMBARKATION DAY?

All cruises disembark by 10:00 AM.

WHAT’S THE EARLIEST FLIGHT I CAN TAKE WHEN I DISEMBARK?

DOMINICA  10:00 AM

GREECE  7:00 AM

GRENADA  10:00 AM

ST. KITTS  9:30 AM

ST. LUCIA  2:00 PM

ST. MAARTEN  1:00 PM

ST. VINCENT  11:00 AM

TURKS AND CAICOS (PROVIDENCIALES)  9:30 AM

TORTOLA  9:30 AM

CAN YOU RECOMMEND A HOTEL?

From bed and breakfasts to villas and resorts, you’ll find accommodations in a style and price to suit your needs. Take a look at our preferred partners on our hotels page .

SPECIAL DIETS

Vegetarian and gluten free diets are available on board; just speak with your chef when you arrive. Vegan, kosher, and other more restrictive diets cannot be accommodated. Anyone with life-threatening food allergies should not sail, as there is always the possibility of cross-contamination in our small galleys.

BOOKING YOUR CRUISE

I’m ready to book my cruise. what’s the next step.

Book online or give us a call at 877.772.4549. A non-refundable deposit of $750 pp is required on 6-night sailings, or $1500 pp on premium cabins. The non-refundable deposit on 10 and 12-night sailings is $1500 pp. Balance is due no later than 90 days prior to sailing. Full payment is required if reserving online or within 90 days of sailing.

PASSPORTS REQUIRED

Welcome aboard.

You’re about to embark on the best vacation of your life! We want to make sure that you feel comfortable every step of the way. Take a moment to read this short guide, with answers to the most commonly asked questions. If there is anything else you'd like to know, give us a call or email. We’re standing by to lend a hand!

WHERE IS THE SHIP DOCKED?

DOMINICA To be determined GREECE Kos Town, Kos Island or Lavrion in Athens, Greece GRENADA Port Louis Marina, St. George’s ST. KITTS Timothy Beach Resort, Frigate Bay ST. LUCIA Rodney Bay Marina, Rodney Bay ST. MAARTEN Great Bay, Philipsburg ST. VINCENT To be determined TURKS AND CAICOS (PROVIDENCIALES) South Bank Marina, Turks and Caicos (Providenciales) TORTOLA Village Cay Marina, Road Town

GETTING TO THE SHIP

It's a breeze to make your own way to the ship on boarding day! Taxis are readily available at hotels and guest houses.

HOW CAN I GET TO THE AIRPORT (OR MY POST-CRUISE HOTEL) AFTER MY CRUISE?

Your crew will assist you with arranging post-cruise airport or hotel transfers.

BOARDING TIME

Any changes in boarding information will be included with your final boarding instructions.

SUNSHINY DAYS

How’s the weather.

The weather is wonderful. Year round temperatures are typically in the mid 80’s, with fresh breezes during the day, and mid 70’s at night. Occasional rain showers are typical, but then the sun shines more brightly afterwards, as if to apologize!

If you're sailing the Greek Isles, prepare for cooler temperatures in May and October. A jacket and slacks are recommended.

WILL I GET SEASICK?

If you've experienced motion sickness in the past, or aren't sure how you'll adjust, please bring your preferred remedy with you. Most motion sickness medications aren't effective if taken after you start feeling sick. Play it safe if you're not sure, and take your medication before you set sail!

MONEY MATTERS

Do i need local currency.

NO CASH is accepted on board the ship.

The US dollar is accepted in most Caribbean ports. The Euro is accepted in the Greek Isles and most French Caribbean ports. Small denominations are best.

Visa and MasterCard may be used in most shops and restaurants. Avoid fraud alerts and pesky holds on your credit card by notifying the issuing bank of your intended foreign travel.

TIPS ABOUT TIPPING

Suggested amounts:

DIAMANT + VELA  Six-night sailings: $250 per person   |   Twelve-night sailings: $500 per person

LYRA  Six-night sailings: $450 per person   |   Ten-night sailings $750 per person

Gratuities are payable ONLY by credit card at the end of your cruise. No cash is accepted onboard.

STAYING CONNECTED… OR NOT

Will i get cell phone coverage.

Most cell phone carriers provide international roaming service on Caribbean networks. Call your provider to ensure you have coverage, and ask about cost-saving international service plans.

DO THE SHIPS HAVE WIFI?

WIFI is available on board Lyra. There are Internet cafés on some of the islands.

SIPS ON THE SHIP

Is there a bar on board.

You may help yourself to the included beverages at any time. You're welcome to bring your own spirits on board to mix your favorite drinks. Pick it up at the duty free on your way down, or at a local market before you board.

DO YOU PROVIDE MIXERS?

Depending upon availability, we provide Cola, Diet Cola, Sprite, Ginger Ale and Tonic Water.

MUSIC TO YOUR EARS… AND OURS TOO

Can you play the kazoo? Have you mastered the art of strumming the guitar on your front porch swing? If you’re wildly entertaining, or mildly talented, bring your instrument along for the ride. Some guests enjoy center stage, while others just like to watch.

While we’re on the subject, bring your playlist, and take your turn at the dock. See what we did there? He-he.

DO YOU OFFER TOURS?

Greek Isles Your crew will explain the wonders of each island prior to your arrival, and may be able to assist if you wish to plan a special activity.

Windwards and Turks & Caicos These islands are small, beautiful, and far from the crowds. Island tours in some ports of call can be arranged with local taxi drivers, or your crew. The main activities are swimming, snorkeling, strolling around local villages, and....relaxing!

The British Virgins | Leewards | French West Indies These Islands are larger, more populated, and have a wide variety of activities and things to do. The Operations Manager will review things to do on your own, as well as a variety of optional extra excursions (not included in your cruise fare).

OF BEACH DAYS AND BEACH SIPS Please do not bring beverages ashore from the ship, as local vendors earn their livelihood selling drinks and renting chairs in some ports of call. When permissible, the crew will bring a beverage cooler to the beach for your enjoyment.

HOW ABOUT SNORKELING AND SCUBA? Snorkel gear is available onboard at no cost. If you are interested in scuba diving, research diving opportunities prior to sailing, and make arrangements while on board.

LOOK SUNSATIONAL The sun can be your best friend and give you a big dose of vitamin D — or your worst enemy. We strongly suggest using a high SPF sunscreen, and applying it often. We want you to look like you’ve been frolicking in paradise, not bathing in a cauldron of hot water. While we’re on the subject of encouraging… avoid insect bites by using insect repellent anytime you are outside. Apply after sunscreen.

THE ESSENTIALS

Island style.

Dress on board is casual. Ladies and gents planning to dine ashore may want to pack a sundress or a pair of trousers. Bath towels are provided, as are hair dryers, shampoo, and body wash.

Cabins have A/C and 110V electric outlets. There are 220V electric outlets aboard Lyra. CPAP machines are okay to bring if you require one. Pack light. Cabin storage space is limited. Did we say pack light? Why yes, yes we did.

SAMPLE PACKING LIST

  • Swimsuit (2)
  • T-Shirts & Shorts
  • Sundress/Trousers
  • Light Jacket/Sweatshirt
  • Sunglasses / Reading Glasses
  • Comfortable Walking Shoes
  • Beach Towel
  • Re-usable water bottle
  • Personal Toiletries
  • Personal Medication (pack in carry-on)
  • Suntan Lotion / Sunscreen
  • Insect Repellent / Towelettes
  • Mask & Snorkel if you prefer your own
  • Water Shoes

Island Windjammers Trading Co. Check out our limited-edition ship logo shirts, hibiscus ball caps, and beach towels.  Click here to shop.

DON’T FORGET YOUR BOARDING INSTRUCTIONS, RETURN FLIGHT INFORMATION, AND PASSPORTS. KEEP THEM IN YOUR HAND LUGGAGE, ALONG WITH YOUR MEDICATION.

Travel delays and emergency contact:

877.772.4549

SEE YOU ON DECK!

Shore leave, even sailors need a little shore time.

Our home ports offer accommodations in styles and prices to suit your needs, from bed and breakfasts to villas and resorts. Browse online, or check out some of our guest favorites, featured here.

Albergo Gelsomino Hotel, Kos Town

barefoot sailboat cruises

Kos Aktis Art Hotel, Kos Town

barefoot sailboat cruises

Kosta Palace Hotel, Kos Town

barefoot sailboat cruises

Sea Glass Place, St. Georges

barefoot sailboat cruises

Allamanda Beach Resort, St. Georges

barefoot sailboat cruises

Radisson Grenada Beach Resort, St. Georges

barefoot sailboat cruises

True Blue Bay Boutique Resort, St. Georges

barefoot sailboat cruises

Bay Gardens Beach Resort and Spa, Rodney Bay

barefoot sailboat cruises

Timothy Beach Resort, Frigate Bay

barefoot sailboat cruises

Marriott’s St. Kitts Beach Club, Frigate Bay

barefoot sailboat cruises

Holland House, Philipsburg

barefoot sailboat cruises

Pasanggrahan Boutique Hotel, Philipsburg

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Seaview Beach Hotel, Philipsburg

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Maria’s by the Sea Hotel, Road Town

barefoot sailboat cruises

Sebastian’s on the Beach, Apple Bay

barefoot sailboat cruises

TURKS & CAICOS

Ports of call resort, grace bay.

barefoot sailboat cruises

The Sands at Grace Bay, Providenciales, Turks and Caicos

barefoot sailboat cruises

Sibonne Beach Hotel, Grace Bay

barefoot sailboat cruises

Pre and Post Cruise Transfers

Getting around the islands is a breeze. Taxis are readily available at airports and hotels in all of our ports of call.

You may prearrange arrival airport-to-hotel transfers, and hotel-to-ship transfers on boarding day, in Greece, Grenada or St. Lucia using our known drivers.

Your crew can assist with arranging post-cruise airport or hotel transfers in all ports.

Vangelis Dimitriadis

Email: [email protected] Phone: 30 697 425 6739

Kerry Cyrus, aka Foxy

Airport Transfers, hotel to ship transfers, and island tours Email: [email protected] Cell/WhatsApp: 473.409.4473

The Other Tour St Lucia

Airport transfers, hotel to ship transfers, and boutique island tours Website: theothertourstlucia.com Email: [email protected] 758.716.2267 Use promo code IWJ10 when booking your transfer online, and receive a 10% discount

Island Windjammers Boarding Instructions

Passport and flight documents.

Please carry your cruise confirmation, your passport, and proof of return flight. Your passport must be valid for at least six months beyond the dates of your trip. Some airlines will not allow you to board if this requirement is not met.

Your passport serves as your boarding pass.

BOARDING INSTRUCTIONS

Early boarding is not permitted.

GREECE, KOS TOWN Boarding time 2 PM. Lyra will be docked in the main harbor of Kos Town, along the main promenade, directly across from City Hall (Address: Akti Kountouriotou 7, Kos). You may drop your luggage at the yacht any time after 12 noon. There are numerous cafes, restaurants, and shops along the harbor front to keep you busy until boarding time!

GRENADA Your meeting place is the Knife and Fork Cafe in Port Louis Marina. Please leave your luggage outside the cafe, as space is limited. You’ll be met by a crew member at 12:30PM, and accompanied to the ship.

ST. KITTS Your meeting place is the outside deck of Sunset Cafe, located at Timothy's Beach Resort. You’ll be met there by a crew member at 2PM, and accompanied to the ship.

ST. LUCIA Your meeting place is Café Ole /Boardwalk Bar located at Rodney Bay Marina. You'll be met there by a crew member at 2PM, and accompanied to the ship.

ST. MAARTEN Your meeting place is the Greenhouse Restaurant located in Philipsburg (not Simpson Bay). You'll be met there by a crew member at 2PM, and accompanied to the ship.

ST. VINCENT To be determined.

TURKS AND CAICOS (PROVIDENCIALES) Your meeting place is South Bank Marina located at 1 Long Bay Highway at 3 PM. The marina restaurant is closed on Sunday. For your comfort, we suggest arriving as close to boarding time as possible.

TORTOLA Your meeting place is the restaurant at Village Cay Marina in Road Town. You'll be met there by a crew member at 2PM, and accompanied to the ship.

Disembarkation in all Ports of Call:

Disembarkation is no later than 10 AM

FLIGHTS HOME

The following is the earliest recommended departure flight time for each port:

GREECE  12:00 PM

Island Windjammers

ALWAYS ON ISLAND TIME

phantom catamaran greece

phantom catamaran greece

Sailing Virgins

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9 Things You Need For Great Barefoot Cruises

Get this right and you'll have the best. vacation. everrrr....

Barefoot Cruises are some of the best vacations you'll ever have. No shoes = barefoot = warm weather = ohh yeah. Gather a few of your loved ones. Go to a place with plenty of water and blue sky. Create your own [authentic] adventure. There are a few things to consider to get into Barefoot Cruises. None of them are too difficult. Here are some tips on what you need:

1. You need a boat.

True that.  Catamaran or monohull? While sailors could debate this one for hours, one thing they would all agree on: a catamaran has a more square geometry (=more like an apartment) and has its main space looking out over the water. These two things mean that for a family or bunch of friends wanting to do barefoot cruises, a catamaran is the way to go.

barefoot cruising sailing virgins

2. You need to know about boat length

Boats are volumetric. Their quoted dimension is linear. This can be deceiving. Let me explain: The difference between a 40' boat and a 44' boat is only 4 feet isn't it, or 10%, right? Well, wrong. Let's oversimplify and say that 40' boat is 10' wide and 10' deep. This means its volume is therefore 4,000 cubic feet. Now let's look at the 44-foot boat.  This 44-foot boat has increased *all* three of its dimensions by 10%, so it is 44' long, 11' wide and 11' deep. This equals 5,324 cubic feet. That's 33% larger by volume. Even though length only increased by 10%.  See what I mean? If you want help with sizing your boat, feel free to email me .

WhatsApp Image 2022-06-21 at 02.22.55

3. You need a skipper

There are a few ways to move your boat around on barefoot cruises:

  • Hire a skipper : through your charter company or a great new Airbnb-like service called  Antlos .  A charter company just tends to give you whoever they have available.  This can be quite a gamble as the skipper/instructor sets the tone on the vacation. Antlos gives you more transparency when choosing your boat/skipper;
  • Do it yourself : if you have the skills/experience you can skipper yourself (see this post  to see if you have the necessary skills), or;
  • Hire an instructor : you can rent an instructor who will not only be your skipper but also teach you the skills necessary to skipper all future vacations yourself. Full disclosure: the instruction part is what Sailing Virgins does. It's awesome.

WhatsApp Image 2022-06-21 at 02.22.55 (1)

4. You need Navionics

Your charter boat should [by law] come equipped with charts. You can also get some great apps to help you. There are a few out there but my favourite is called Navionics . It works on iPhone or Android (I have tried both, iPhone works best). It sells app by regions.  A region will cost around $20. This will get you all charts on the entire coast of the region you have chosen. Amazing really. Make sure you download not just the app but the individual areas you want. This is a two step process. Do this before you leave good wifi. You've been warned!

5. You need to know your weather

There are some great weather services out there.  Get more than one so you have a second and third opinion.  Check out Fastseas.com for an awesome route planner (and our blog post about this here ).  Put these apps on your iPhone: WeatherTrack , PocketGRIB and Windfinder .  If you have Android get Meteo Marine ,  NOAA Weather  and any GRIB apps such as  SailGrib .

6. You need to get there

You may have your favourite travel app. If you don't try Skyscanner and Google Flights . Tripadvisor provides crowd-sourced advice but like any guide, paying too much attention to this may take the discovery out of your holiday.  Use sparingly!

7. You need list of books to read

Needed an excuse to buy a Kindle? Well, this is it. One thing a sailing vacation is good for is reading. No television on board (if there is one just pretend there isn't). If you have wifi make sure you limit it to an hour or two each day. Then you can live a little! Just sailing, swimming, listening to music, reading, eating, exploring, and relaxing. This is what life is about. One thing sailors tend to do a lot of is read.  If you're looking for books, email me . I love giving reading recommendations.  If you have any recommendations yourself, put them in the comments below.

8. You need cooking tips

Ask whoever is providing your boat if they have measuring cups and spoons. If not, take some with you. And a knife sharpener. Being on a boat is great for getting experimental and creative with cooking (if that's your thing). You are limited by a pretty small oven. But it's surprising what you can do (and how much fun it is) when you feel free.  Bake bread, make pancakes, gourmet fish dinners.  It's all possible.  Get weird.  Stay tuned to this blog for boat-specific sailing recipes.

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9. You need to travel light

I could go on and on about traveling light. This should suffice: no matter how light you pack, there is something in your bag you will not wear during your vacation. If you're on a boat for a week you need almost no gear. For guys, I recommend two swimsuits, three t-shirts, two shorts, one polo, underwear, flip-flops, hat. For girls, if you like remove the polo/shorts and add a dress or two.  That's it. Honest. When you walk on a boat with hardly any luggage in a collapsable bag, don't be surprised if the skipper/instructor hugs you.  Rather than say to yourself "I may need that" go out on a limb and say "what do I absolutely need?".  You'll feel so much better when you do this.

Barefoot sailing cruises (otherwise known as bareboat cruises) are a fabulous way to spend a week with your loved ones (be it family or friends or both).  They are much easier to do than many people realise.  Even if you have never sailed before.  This post provides nine tips to those who are seeking information on how to do their first cruise.  We hope you enjoy this!

Sailing Virgins provides qualified sailing instructors and runs fast-track courses in the Virgin Islands. Leave a comment below to be sent a one-page pdf summary of this article. If you have any questions please  email me to arrange a time for a free sailing vacation consultation.

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The founders of Sailing Virgins started things as a result of having some incredible sailing seasons in the Mediterranean and Caribbean working for sailing company The Yacht Week. James then worked for and for a while managed Tortola Sailing School. In 2016 he branched off and started Sailing Virgins. We LOVE how sailing is changing. Top speeds in the America’s Cup were thirteen knots not so long ago. Now they’re 45 knots. If you’re excited by that, we’re with you. Giddy up!

  • Wickhams Cay 2 Road Town, Tortola VG1110, British Virgin Islands
  • +1 (272) 999-1920
  • [email protected]

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barefoot sailboat cruises

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  3. Windjammer Barefoot Cruise (alas, the ship we were on is now at the

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  4. Windjammers Barefoot Cruises, Fantome!

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  5. BAREFOOT SAILING CRUISES (Nassau)

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VIDEO

  1. Getting The HARDTOP UP! Boat Work (Barefoot Travels S4 E56)

  2. Eclipse of 1998 on the S/V Mandalay from Windjammer

  3. Abandoned Sailboat

  4. Windjammer Barefoot Cruises

  5. 7-Night Northern Lau Highlight Reel

  6. Birmingham Canal Boating 2024🇬🇧//Spring Vibes//Birmingham Blogs

COMMENTS

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  2. Island Windjammers Barefoot Cruises

    About Island Windjammers. Island Windjammers offers 6, 10, and 12 night Caribbean and Mediterranean sailing cruises out of Grenada and St. Maarten. Our sought-after 12 night Explorations cruises, extended Wanderer Cruises, and other featured trips such as our annual Rum Cruise are also offered periodically throughout the year.

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  8. Vela Cruise: Expert Review (2023)

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    Improve this listing. Similar Experiences. Luxury Catamaran Cruise: Sip, Sail, Snorkel, and Swim with Pigs! 19. Catamaran Cruises. from. $225.00. per adult. Bahamas Sunset Sail and Dine with Spectacular Views.

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    louisbM5805UHJune 7, 2022. We (2 couples) booked a 7 day private charter with Barefoot, incl. an instructor/captain and a chef. We did our ASA 101 to 104 certificates and sailed for a week ... read more in perfect (very windy, 20 to 30 knots) conditions. Brian, the captain/instructor was very patient and a great teacher.

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    No shoes = barefoot = warm weather = yessss. Gather a few of your loved ones. Go to a place with plenty of water and blue sky. Create your own [authentic] adventure. There are a few things you need to get into Barefoot Cruises. None of them are too difficult. Here are some tips on what you need: 1. You need a boat.

  15. St. Vincent & The Grenadines Bareboat Charter Fleet

    Racing Fleet. Embark on a sailing adventure of a lifetime with Barefoot Yachts' race charters in the Caribbean! Picture yourself on the tiller of a professionally maintained, high-performance sailboat, cutting through the azure waters of the Caribbean. Experience the exhilaration of competitive racing and join the ranks of international ...

  16. Barefoot Cowboy Custom Caribbean Adventures

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  17. Bareboat Sailing Charters

    About Our Charter Boats. We specialize in new and near-new Beneteau and Jeanneau sailboats ranging from 42 - 45 feet. Start your Newport, RI sailing charter adventure in the most famous harbor in America …Newport, Rhode Island. Also, we are the largest bareboat yacht charter company in New England! Our Fleet.

  18. Plan Your Cruise: Island Windjammers

    Book online or give us a call at 877.772.4549. A non-refundable deposit of $750 pp is required on 6-night sailings, or $1500 pp on premium cabins. The non-refundable deposit on 10 and 12-night sailings is $1500 pp. Balance is due no later than 90 days prior to sailing.

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    A variety of cruises are offered aboard the Genesee Belle Paddlewheel riverboat throughout the summer. Reservations are required for all meal cruises. Lunch cruise tickets must be purchased in advance. Reservations for the lunch cruise are accepted until the preceding Wednesday (based on availability). Specialty cruise tickets may be purchased in advance or on the boat based on availability....

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