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Virgin Islands Tall Ship Sailing

Sail aboard the tall ship LIBERTY STAR for a Caribbean Windjammer Cruise in the Virgin Islands. On each sailing cruise, we explore the islands of the BVI under sail.  Each trip BVI Windjammer Cruise is unique, so come see where the wind will take us.  On a Liberty Fleet windjammer cruise, you can relax and unplug or decide a more adventurous cruise and take a turn at the helm, help hoist the sails, and even navaigate with our captain! Come explore what a Virgin Islands Sailing Vacation has to offer on a Caribbean Windjammer Cruise.

Cruise Reviews
Virgin Islands Pace of Life
Things To Do
Weather and Climate

Virgin Islands Windjammer Cruise Reviews

Captains Blog: Sea Turtles, Dolphins and a week full of adventuring aboard the Liberty Star in the BVI's
Virgin Islands Sailing Vacation Cruises
Capt Jon Cook here sending out some good vibes from the Virgin Islands, aboard the Liberty Star. This week was full of fun and adventure starting out with an amazing sail into Great Harbor, Jost Van Dyke. We were able to sail right onto the anchor, always a treat. With an amazing group of passengers we explored some new spots including the beautiful beach resort at Nanny Cay, Tortola, where we all made some new friends and new memories.
The sailing all week was nothing short of amazing on our traditional schooner in the trade winds that have been sailed upon for centuries by these beautiful ships. As if the sailing wasn't enough, we were also able to do some hiking, swimming, and snorkeling to take in the beauty of all the on land and below the water inhabitants. The sea turtles were very active this week and were spotted several times a day and we were even treated to the company of a pod of dolphins guiding us to their favorite spots.
I will also have to take a second to mention all the wonderful food on board as our ship's cook, Sue,is able to prepare 5 star meals that are a real treat to your taste buds It's hard to beat enjoying her food while watching the the sunset over the mountains of the islands. 
Until next week
Capt Jon Cook
Schooner Liberty Star
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Captains Blog: Full moon party at Trellis Bay, and more great tall ship sailing throughout the week!
Virgin Islands Sailing Vacation Cruises


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 stop on the way to everywhere", as they were a pinnacle stopping point throughout all the trade routes for the Spanish, English, Dutch, and French.
This week was, as always, filled with great weather, beautiful sailing with great winds, and the necessary swim calls and snorkeling spots! 
See you next week,
Captain Jon Cook
Schooner Liberty Star
Liberty Fleet of Tallships 
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Captains Blog: Bringing in the New Year aboard the Schooner Liberty Star with Moku Jumbies, fire dancing and new friends
Virgin Islands Sailing Vacation Cruises
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 up a traditional touch of the islands with a traditional way of exploring them makes a memorable trip for all while even getting the passengers to help sail the boat down the Sir Francis Drake channel past all of the historic Virgin Islands. So make sure to come down and share the experience soon!


Capt Jon Cook
Schooner Liberty Star
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Captains Blog: Sailing with the rail in the water, great sunsets and new friends made aboard the Schooner Liberty Star in the BVI's!
Virgin Islands Sailing Vacation Cruises

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 in the water for part of it. 

It really doesn't get any better than the weather in the BVI's. It was sunny, warm and beautiful for the whole week (much nicer than our Boston counterparts!). Once we reached our first destination in Jost Van Dyke, we quickly went for a swim call off the boat, and started snorkeling. This became a ritual as every day was filled with flips of the bowsprite, cold beverages on deck, and of course myself blowing the conch shell to let the sun know its okay to go down! 


Highlights? I could mention Willy T's, or the baths at Virgin Gorda, but I'm gonna have to say its the 6 new friends I made. Everyone comes on as a guest here, and leaves almost as family. 

That's all for now. Until next time! 


Captain Jon Cook

Liberty Star


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Enjoying Thanksgiving Under Sail on the Liberty Star in the BVI
Virgin Islands Sailing Vacation Cruises

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 for the afternoon ashore at Leverick Bay. Yesterday, we spent the night at Trellis and went ashore to listen to a band - loved it!  Today we find ourselves sailing to Norman Island, we're going into the treasure caves and then to the Willie T's tonight for a little post turkey celebration.


Captain Jon Cook & the crew of the Liberty Star

PS: We can't wait to take you sailing too!

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What an INCREDIBLE way to celebrate a 60th birthday aboard a windjammer in the British Virgin Isles
Virgin Islands Sailing Vacation Cruises
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 integral team and have, this week, welcomed us into your sea faring family in the Caribbean. 
         We hope that our paths will cross again and, in the interior, encourage you to fulfill your dreams. 
         You are all awesome! Thank you for the wonderful memories.
Signed Carol B & Don P
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First timers aboard the Schooner Liberty Star in the BVI's
Virgin Islands Sailing Vacation Cruises
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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Great time in the Virgin Islands and Bubbly Hole on a Tall Ship!
Virgin Islands Sailing Vacation Cruises

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!!!!

Bubbly Hole at Jost van Dyke!


Bonnie F.



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First sailing vacation in the BVI's aboard a classic tall ship!
Virgin Islands Sailing Vacation Cruises

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 Captains that they have sailed under because of his demeanor.


          Tia, who cooked for us was awesome as well. Not only was her food amazing but talking to her and experiencing some of the excursions with her were just as awesome. She always had a smile  on her face and took extra care of us. She was willing to change up the meals to meet our varied palates and never complained about doing so either. She is an amazing woman and has done some extraordinary things. She supplies lots of laughs but also some down home comfort when needed!! She is a keeper.

          Scott the deckhand..or dinghy captain as I liked to call him had to be the most entertaining person on the ship. Granted he is a young kid, but his knowledge of sailing exceeded his age. He knew so much about it and was always willing to teach us about sailing ,that it made the trip so much more enjoyable. He was hilarious and was never afraid to laugh at himself. He was the one we spent the most time with, as he was in charge of taking us to shore all the time...and he made those trips exciting. He was a complete and utter gentleman, and would help us when ever we needed anything. A lot of nights, he was our main entertainment...and he never let us down. For being a 19 year old on a ship in the Caribbean, he never once let his professionalism slip. And that amazed me. He definitely made me smile...ALOT!

        The entire crew were amazing and I think that helped make the trip so much more enjoyable. They allowed Josh and I our space when we wanted it, and came and talked to us when we got tired of each other :). It was definitely worth every penny and I would do it again in a heartbeat!!! 


I can't say enough about Liberty Fleet. From the excellent and speedy customer service at the booking stages to the amazing service we got on the trip, it is a well run machine and company. I loved every minute of it and was relaxed the entire time!! I will be more than happy to do another trip and recommend to friends and family!!!

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Tall Ship Windjammer cruise on the Liberty Star in the British Virgin Islands
Virgin Islands Sailing Vacation Cruises

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 first time to the Virgin Islands. I felt like we received an intimate, personal tour of all of the best places including the well known and little known.  Carlos provided history of the area or ship wreck when he knew the history. Everyone had a wonderful personality and felt like family after just one day on board.  I can't say enough about the crew.  I will recommend d this to friends and family. In fact, I hope to get enough to join me to fill the Liberty Star next winter on another cruise in the BVI!


Josh G. 

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Fun, memorable cruise aboard the Tall Ship Liberty Star in the Virgin Islands
Virgin Islands Sailing Vacation Cruises

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.




   Tricia M.



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Great crew and food aboard Tall Ship Windjammer in the British Virgin Islands
Virgin Islands Sailing Vacation Cruises

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 other cases  in restaurants (and stores) in the US, whole grain, healthy choices were scarce. However, Tia's salads were great, including raw cabbage, lettuce, beans, etc. I am extremely impressed by what Tia succeeded to make and bake in that small galley. Her organizational talents were immense, I cannot even imagine how she managed to store and find the ingredients.


Claus & Wenche B. 

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Virgin Islands Destinations...


bvi map2

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.  Learn about some of the places we may visit on your Virgin Islands sailing cruise.


We do not have a set itinerary on any of our Virgin Islands Sailing Cruises so that each trip is truely unique.  Our captain will customize each trip to the unique needs and desires of our guests.



Some of the places that you may visit...


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. And there are several fun dining spots that are all 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.

coki beach

    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:

sunset at beach bar

    Jost van Dyke:

    This island, the westernmost of the British Virgins, is home of White Bay beach, the Soggy Dollar Bar, and Foxy's. Named after a 17th century Dutch pirate, Jost Van Dyke has a sleepy Caribbean air 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 spot!

    • Sandy Cay:
             We may anchor just south of Sandy Cay; it's literally a beach island, we love it and think you will too!
      • Tortola:
              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 The Baths - one of the Caribbean's natural wonders, a spectacular formation of gigantic boulders, creating 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. 
    The Baths  Virgin Gorda Island  British Virgin Islands  West Indies


    • 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.  And 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.
    Willy T Bar Restaurant





    Virgin Islands Pace of Life

    Liberty Windjammer Cruises in the Virgin Islands on our Tall Ship Liberty Star offer a very laid back beach and boating vacation.  We will sail throughout the British VIrgin Islands on our weekly all-inclusive Virgin Islands sailing vacations.  The Virgin Islands are not as remote as the Bahamas, we will share our anchorage each night with a flotilla of other smaller sailing boats.  These trips are generally described as:

    • Fun - In the Virgin Islands, the next stop is never far away and with unlimited warm water, lots of activities and an abundance of great beach bars, you're sure to have a blast!
    • Laid back - take off your watch, turn off your phone and unplug!
    • Great Sailing - The Trade Winds keep the sailing fresh and fun and keep the temperature just right!
    • Water Focused - Liberty Star offers a lot of water activities: snorkelling, beach trips, paddleboarding, and swimming.  The BVI also host some great wrecks that you can snorkel on your sail.
    • Intimate - With just six guests per cruise, Liberty Star offers a wonderul intimate experience on a ship large enough so that you'll have plenty of space for yourself.

    The 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 sailors 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.

    Cruising Grounds: Things To Do

    Visit a different spectacular beach every day.

    beach to ship with beer cropped           DSC03448


    Relax on the beach or on the ship. 

    sunbathing on deck                     Andy and Stefan


    Snorkelling in the Virgin Islands is fantastic. 

    Yellow fish


    Relax listening to live music at a beach bar, test out the signature rum drink at each beach bar you find (bring a buddy for this one!)


    Quito           rumpunch


    Dive a wreck.  Hike a trail. 

    Enjoy the food. Enjoy the sailing.




    Virgin Islands Weather and Climate information...

     calm clipper panorama

    The British Virgin Islands enjoy a gorgeous tropical climate, moderated by trade winds. Temperatures vary little throughout the year. In the capital, Road Town, typical daily high tempertures are around 90°F in the summer and 85°F in the winter. Typical daily low temperatures are 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. The Liberty Star's schedule is structured to avoid hurricane season.


    Climate data for Virgin Gorda, British Virgin Islands















    Average high °F














    Average low °F














    Precipitation inches














    Source: Intellicast


    palm tree beach






    On Virgin Islands Sailing Vacations are week-long all-inclusive windjammer cruises where you'll discover secret parts of the BVI from our sailing ship. Each day, we will set sail for a new destination and a new adventure. Be design, we don't have a set itinerary so that our Captain may plot your course for the best wind and weather to make each trip unique and fun. You'll love sailing the Caribbean on our Tall Ship and hope you'll join us this winter for a different type of cruise, a tall ship cruise!

    For more information, you may explore our website:

    We look forward to sailing with you soon!