Virgin Islands Windjammer Cruises

Virgin Islands Info
Port St. Thomas, USVI
Schedule Sunday - Saturday
Season November - July
Age Requirement   18 and older
Max Passengers 6

Virgin Islands 01Join us aboard the LIBERTY STAR for a Virgin Islands Windjammer cruise where you'll discover secret parts of the US and British Virgin Islands from our sailing ship. Each day, we will set sail for a new destination and a new adventure. Join us for a week of island hopping from fantastic beaches to famous watering holes and historic ports that can only be found sailing in the Virgin Islands!


  Good afternoon from the Virgin Islands. Good afternoon is the proper way to greet locals in this region and if you hear it, the proper response is just to say, "Okay". The local culture is certainly always a highlight of these sailing adventures. We were able to surprise our guests this week with attending the Full Moon party at Trellis Bay, Beef Island.     (Full Moon Party)   Full of rich culture and local artwork, this place is a microcosm of the island culture. Being able to sail all around these islands on a traditional schooner brings us even closer to this feeling of being part of the local culture as tall ships in the days of yore called these islands, "the sto...
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Greetings from St Thomas on the Liberty Star! What a great week down in the islands to bring in the new year with some great wind, sailing, and passengers. With the wind filling the sails and the rail in the water we made our way up to Virgin Gorda. Then it was nothing but smooth sailing from there as we made our way to some of the best spots in the islands and were able to stop to cool down in the water during the amazing snorkeling adventures.   It's hard to beat a New years party at Trellis with the local art community throwing an extravagant event with a great touch of local traditions and culture including Moku Jumbies, local music, and fire dancing.       Matching...
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Captains Blog!  Greetings from St. Thomas, Red Hook aboard the Liberty Star! I'm going to try to keep a Captains Blog updated around once a week, so I hope you will tune in and join us for our adventures! This week we departed Red Hook on Monday morning at about 0700. Leaving the dock was uneventful (phew).  With a great wind direction, we decided to raise all of the Star's sails, and called on our guests to come help us out! She's a smaller schooner, so it doesn't take as much manpower as her larger friends, but it doesn't take away from the beauty of hauling on a halyard! With winds at about 15 knots and above, we enjoyed an awesome sail over to the BVI's, with the rub rail ...
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We just kicked off our season on the Liberty Star this past Sunday! We're having a blast so far and I can only imagine what treats that cook Sue has in store for us later today. We welcomed our guests aboard on Sunday evening at Red Hook and had a nice reception for them with some goodies from the galley and just one or two cold beverages... On Monday morning, we started the week sailing from St Thomas to Jost Van Dyke and were able to visit Bubbly Hole that morning before heading ashore to Foxy's for a fun filled Monday night...  On Tuesday, we sailed across to Virgin Gorda stopping a few times along the way and spent the night anchored in Gorda Sound. I loved swinging in a hammock fo...
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Where do we begin to tell you what a wonderful adventure you have given us? We set sail on December 2, Don's 60th birthday from St. Thomas on the Liberty Star. Perfect weather, a perfect start to the 7th decade. Thank you for introducing us to schooner life aboard the Liberty Star, to hoisting sails, coiling the sheets and halyards, knot tying; to your favorite snorkeling spots, beaches, bars, the glass blowing and Caldwell distillery in Cane Garden Bay, and the adventure of Captain Long Jon Anchor Gone Wrong, off of Sailor's Rest.         You have each in your own way, with your own unique talents, skills, and passions, enriched our experience. Together you form an integ...
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This was my first sailing trip aboard a windjammer in the Caribbean and it was fabulous. Kyle was a great sailing dinghy captain. Clint was a fantastic leader through the baths and the caves. Cory with his sailing paddle board. Sue, all the food was to die for. And Captain Jon, what a great ride we had with you. I think we'll spend some time in a boat somewhere. The week couldn't have been better. How quickly you all took in four strangers and let us become part of your family. Thank you all so much and remember; "Stay out of my swing!"   Signed Cathy & Tim S.   November 30, 2013  
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yes, our first mate Lee stood  out as someone who sincerely loved the boat and catered to our every wish...he had great stories to tell and was very knowledgeable  about all aspects of sailing,stellar navigation, pirate stories etc. etc. I would say his presence really made the trip more memorable.Sue was a wonderful cook and created some delicious meals and was also very gracious. Carlos was a great captain and took every measure to keep  us safe under his watch.....I would definitely say your fantastic crew is your biggest asset and would recommend this Virgin Island cruise to any of my friends. this trip outdid all my expectations!!!! [embed=videolink]{"video":"file://...
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For my first sailing experience on a tall ship in the BVI's it was incredible. The Liberty Star was just a good enough size for Josh and I to feel included if needed with the crew, or feel like we were on the boat all by ourselves. It helped that we were the only ones sailing this trip, but I am sure if the boat was full, it would still feel the same. The entire crew were phenomenal. The captain gave us tons of options for us to do each day and never pressured us into one thing or another. Carlos was very well informed in terms of sailing and was so calm and gentle with the crew that it made the sailing more enjoyable. Even the other crew mentioned that Carlos was one of the best Captai...
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Capt. Carlos, Mate Scott and Cook Tia were warm and welcoming. All shared stories from their life.  Everyone was focused on making sure we were comfortable and happy. The crew spoke highly of Carlos and everyone was working as a team.  Tia, Scott and Carlos balance each other well.  Scott offered great tips on snorkeling, had patience with rigging questions and made it enjoyable to join in hoisting sail on a tall ship!.  I have to say that your team far exceeded my expectations. Tia ROCKS!  The meals were delicious. She made sure we enjoyed the food and asked about our likes and dislikes. Again, she was fantastic - we basically had a personal chef! This was my f...
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We feel like we've made new friends as the crew was incredible!  I will highly recommend this Tall Ship Windjammer cruise to everyone I know! Tia was an amazing cook and so lovely, friendly and helpful.Lee and Scott were both amazing.  They were both very knowledgeable, funny and very hard working.  I couldn't imagine the trip without them.   Best,       Tricia M.     
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Three sailors loved tall ships and knew so much about such ships and about sailing. Even young Scott at only 19 years had lots of sailing experience and was a certified life guard. ALL FOUR went out of their way to be nice and friendly and helpful. Simply OUTSTANDING!! We were very lucky to have four other fun and pleasant co-passengers, especially two of them. So we all did all we could to contribute to the greatest atmosphere and we laughed a lot and got along beautifully all week while enjoying the laid back atmosphere of the BVI's.  The food was great! for instance, she prepared for me fried egg plant and fried, seasoned tofu instead of pork roast and other meat entrees. As in most ...
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25 years ago Jackie took a bareboat sailing cruise in the BVI and she has been talking about it since we met 15 years ago! To celebrate our years together, we came to the Bahamas to sail on the Schooner Liberty Clipper and live an adventure together. Little did we know how perfect it would be and how much fun we would have.  Thanks to everyone in the crew for making us part of the experience and helping us feel pampered too!  The depth of relaxation and contentment were profound and having no specific agenda was very freeing. We loved what we did, and what we didn't do!  Thanks for the excellent food, the safe harbor, the singing and dancing, ...
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bvi map2


Come aboard and island-hop through the US and British Virgin Islands where some of the most famous beaches (and beach bars) will call to you each day. By design, our Windjammer Cruises do not have a set itinerary so that each trip is truly unique. Our captain will customize the schedule of each week to the unique needs and desires of our guests. Each day is a new adventure!

Check out some of the places we may visit on your trip below!



bvi beautiful beach

US Virgin Islands Locations

St. Thomas: All of our cruises board and disembark from Red Hook in Vessup Bay on the east end of St. Thomas.

  • Charlotte Amalie: A large and protected harbor on St. Thomas.
  • Red Hook Bay: All conveniences and grocery shopping, along with many dining options. Ferry service to St. John and the British Virgin Islands is also available from Red Hook. Several fun dining spots are within walking distance of our dock at American Yacht Harbor if you get into town early! There are also a dozen gorgeous nearby beaches - Coki Beach is especially beautiful.

St. John: St. John is considered the natural gem of the US Virgin Islands and hosts a large national park. On many of our Virgin Islands sailing cruises we will visit St. Johns the first night!

  • Cruz Bay: The "big town" of St. Johns has lots of great entertainment options. Step ashore for a cold-one...
  • Trunk Bay Beach: Located on the north side of St. John, this beach has been selected as a Top 10 Beach by Conde Nast Traveler Magazine.
  • Cinnamon Bay Beach: Located just east of Trunk Bay, this is another beautiful Caribbean beach.


British Virgin Islands Locations

VirginIslands 18Jost van Dyke:

The westernmost of the British Virgin Islands, Jost van Dyke is home to White Bay beach, the Soggy Dollar Bar, and Foxy's. Named after a 17th century Dutch pirate, Jost Van Dyke has a sleepy Caribbean atmosphere and is less developed than other islands in the British Virgins. It is a favorite of sailors who stop for music, dancing and tropical drinks.

  • Bubbly Hole: Get "washed" in this little gem. It's a short hike to get to it and our crew will show you the way.
  • Foxy's: No trip to the BVI is complete without a visit to this world famous watering hole!


Sandy Cay - We may anchor just south of Sandy Cay – the whole island is basically all beach; we love it and think you will too!


VirginIslands 23Tortola

  • Cane Garden Bay: It's not just famous for the song lyrics, it is also home to the Caribbean's oldest continually operated rum distillery. Head ashore and try a sample!
  • Soper's Hole: Tortola's West-End is a fantastic anchorage, come "swing on the hook" and find out why.

Virgin Gorda: When you think of Virgin Gorda, you think of The Baths - one of the Caribbean's natural wonders. A spectacular formation of gigantic boulders creates grottoes and caves that you can explore on foot. The island is home for the famous resort of Little Dix Bay, as well as the Bitter End Yacht Club.

Norman Island: This island is reputed to have inspired Robert Louis Stevenson's Treasure Island! Legend has it that pirate treasure is buried at a natural formation called the Indians, which are half-submerged rocks forming an underwater labyrinth for divers and snorkelers. The island is deserted but for a few seabirds, several footpaths, and the Pirate's Bight Bar. One trail leads to Spy Glass Hill, a challenging half-hour hike rewarding you with fantastic views. Pirates once used this lookout to spot Spanish Galleons returning home with gold and treasure. No visit to the Virgin Islands is complete without a visit to Willy T's Floating Boat Bar, if not for the spectacle at least for the rum!

Looking for more Virgin Islands destinations? Check out our Blog!


Things to Do

bvi onthebeachThe appeal of the Virgin Islands lies in the amazing combination of wonderful sailing, warm and beautiful waters and an abundance of shoreside activities and bars that are never far apart. Unplug in the Virgin Islands and leave the worries of your world behind in this sailor's paradise. When you leave this vacation, you'll have the right mix of activities, fun and relaxation so that you can go back to life refreshed and recharged and not needing a "vacation from vacation."

Besides goats and hermit crabs there are also beach bars on every island. There will be plenty of opportunity to go a shore and enjoy live music, beach BBQ's, and a different rum drink at every watering hole.

From sailing the ship to exploring pink sand beaches to napping on deck, you’ll never be bored during your trip. Since we take each day as it comes, we are open to your suggestions. If there is a place or activity that you are especially looking forward to, you can always feel free to let our captain and crew know!

In the meantime, check out some of the great activities available at your fingertips while sailing on your Virgin Islands Windjammer Cruise:


Water Activities

bvi snorkelLike the LIBERTY CLIPPER, the LIBERTY STAR carries several water toys with her wherever she goes, and you are more than welcome to help yourself!

  • Kayaking
  • - get out on your own and explore beautiful coves and beaches at your own pace.
  • Snorkeling
  • - the Virgin Islands are home to exquisite coral reefs and amazing shipwrecks. Get up close and personal and discover a whole new world!


Relax on a BVI Sailing Cruise


Rest & Relaxation

Just looking for ultimate relaxation? The LIBERTY STAR has you covered.

  • Relax on deck and unwind with a book
  • Lay out on deck in the sunshine
  • Visit the ships bar and enjoy a libation
  • Aft deck seating - great for enjoying a drink as the sun sets!


Island Time

bvi island timeOne of the biggest draws of the Virgin Islands is its plethora of vibrant ports and seaside towns. You'll have the chance to experience a new place each day, along with some world-famous watering holes!

  • Walk along pink-sand beaches, or just relax in the sun on shore
  • Try a new rum drink at different beach bars
  • Hike ruins and explore historical landmarks
  • Nature walks

Weather & Climate

The British Virgin Islands enjoy a gorgeous tropical climate, moderated by trade winds. Temperatures vary little throughout the year. In the capital of Road Town, typical daily high temperatures are around 90°F in the summer and 85°F in the winter. Daily low temperatures tend to be around 75°F in the summer and 70°F in the winter. Rainfall averages about 45.3 in per year, higher in the hills and lower on the coast. Rainfall can be quite variable, but the wettest months on average are September to November and the driest months on average are February and March. Hurricanes occasionally hit the islands, with the hurricane season running from June to November. Our sailing schedule is structured to avoid the majority of hurricane season.

Month Jan Feb Mar Apr May Jun Jul Aug Sep Oct Nov Dec Year
Avg Hi °F 79 80 82 84 85 86 87 87 86 85 82 80 83.6
Avg Low °F 68 67 68 69 71 73 73 73 73 72 71 69 71
Precipitation inches 2.9 2.5 2.2 3.3 4.6 2.8 3.3 4.4 6.1 5.2 7 4.4 48.8

Virgin Islands Sailing Schedule

All Virgin Islands sailing cruises board at 5:00 PM on the start date and disembark at 10:00 AM on the end date. On the boarding night, you'll be responsible for dinner ashore in St. Thomas. Prices below reflect the starting rate of per-person fare based on double occupancy and do not include tax or gratuity.  All cruises are subject to 5% port fee on the total price of the cruise.  Click here to see what is included in the cost of a cruise and for more information about upgrades and add-ons.  Call our office at 617-742-0333 with any questions or concerns.


Virgin Islands Windjammer Cruise!



Virgin Islands 2015-2016 Schedule

Cruise Start Cruise End Embark/Disembark Ship Pricing* Notes Book?
Nov 22, 2015 Nov 28, 2015 St Thomas, USVI Liberty Star $ 1,899 Thanksgiving Cruise BOOK NOW
Nov 29, 2015 Dec 5, 2015 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Dec 6, 2015 Dec 12, 2015 St Thomas, USVI Liberty Star $ 1,799   SOLD OUT
Dec 13, 2015 Dec 19, 2015 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Dec 20, 2015 Dec 26, 2015 St Thomas, USVI Liberty Star $ 1,899 Christmas Cruise BOOK NOW
Dec 27, 2015 Jan 2, 2016 St Thomas, USVI Liberty Star $ 1,899 New Year's Cruise BOOK NOW
Jan 3, 2016 Jan 9, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Jan 10, 2016 Jan 16, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Jan 17, 2016 Jan 23, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Jan 24, 2016 Jan 30, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Jan 31, 2016 Feb 6, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Feb 7, 2016 Feb 13, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Feb 14, 2016 Feb 20, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Feb 21, 2016 Feb 27, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Feb 28, 2016 Mar 5, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Mar 6, 2016 Mar 12, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Mar 13, 2016 Mar 19, 2016 St Thomas, USVI Liberty Star $ 1,799   SOLD OUT
Mar 20, 2016 Mar 26, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Mar 27, 2016 Apr 2, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Apr 3, 2016 Apr 9, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Apr 10, 2016 Apr 16, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Apr 17, 2016 Apr 23, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
Apr 24, 2016 Apr 30, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
May 1, 2016 May 7, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW
May 8, 2016 May 14, 2016 St Thomas, USVI Liberty Star $ 1,799   BOOK NOW

*Per-person price for private double cabin. Single shared cabin subject to 25% supplement fee (125% of above price). Private single cabins subject to 75% supplement fee (175% of above price). Prices do not include 5% port fee, upgrades, or crew gratuity.


Virgin Islands Travel Information

bvi ayhmap

Cruise Boarding / Disembarking

All cruises depart and return to ST THOMAS, USVI.

The LIBERTY STAR is docked at American Yacht Harbor in Red Hook.
(see map).






Cruise Itinerary

Sunday: Boarding begins at 5:00 PM.

 - Board for your cruise on Sunday evening for the Captain's welcome and safety talk.  We depart late that evening or early Monday morning with the tide.
 - Dinner is not provided this evening, so you will need to go ashore.
 - If you arrive early: you may drop off your bags at the ship AFTER 2:00 PM on Sunday.  The ship will be at a mooring until then and you will not be able to leave your things with the marina.
 - If you arrive late: please call the ship's cell phone if you will be arriving after 8:00 PM.  This phone number will be provided to you in your pre-boarding email.  You may also call our stateside office in Boston at 617-742-0333 (we are open until 6 PM EST).

Monday - Friday:   Sailing in the beautiful Virgin Islands!  We have no set itinerary of places to visit and leave it up to the captain's discretion for the best weather and opportunities.  You can of course give suggestions of where you would like to explore!

Saturday: Return to and disembark in St. Thomas by approximately 10:00 AM.

 - We suggest that you schedule your return flight for after 2:00 PM at the earliest.  This will help account for any possible weather delays returning to St. Thomas and give you time to get to the airport and through secruity.


Meeting the Talofa in St. Thomas

Fly to St. Thomas (STT) Cyril E. King International Airport, served by most major airlines.

- Guests traveling from areas with the potential for winter weather delays are strongly advised to consider flying to St. Thomas a day or two before Sunday's departure to ensure you do not miss the boat due to canceled or delayed flights.  Recommended hotels are below!

Take a taxi to the American Yacht Harbor Marina.

- Travel time from the airport to Nassau Yacht Haven is approximately 30 minutes, depending on traffic.
- The marina is in RED HOOK at the eastern end of the island:


Passports & Currency

A VALID PASSPORT IS REQUIRED for this sailing experience as we will be sailing in both US and British Virgin Islands waters.  The Virgin Islands do not require VISAs for United States, Canadian and European travelers.  If you have any questions, please refer to the State Department in your country.  

NOTE: For US Passengers with a Passport Card, you CAN use the card to enter the British Virgin Islands by boat.  If you are flying into or out of a BVI location before or after your cruise with us, you WILL need your passport book.

Currency in the Virgin Islands is the U.S. Dollar.  Guests traveling from the US do not need to exchange currency beforehand.


Recommended Hotels


Things to do in St. Thomas

If you are arriving early or would like to extend your stay, check out some of these attractions on the island of St. Thomas!