Virgin Islands Windjammer Cruises

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

Virgin Islands 01Currently the LIBERTY STAR is resting up for the 2018 Boston sailing season, but please check back for future Virgin Islands Windjammer cruise options where you'll discover secret parts of the US and British Virgin Islands from our sailing ship.



In the mean time, we will leave this cruise description right here, so that you can day dream a bit:

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!



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


More information on Virgin Islands Sailing Vacations...

We invite you to explore our website for more information about our Virgin Islands sailing vacation cruises aboard the Liberty Star.

We Hope to sail the Virgin Islands with you soon!

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 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 Liberty Star 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!