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Windjammer Cruises | Schooner Liberty Star

Set sail for a windjammer cruise aboard the tall ship LIBERTY STAR.  The Windjammer Liberty Star is a 67-foot wooden schooner that features three comfortable cabins.  She offers Virgin Islands Sailing Vacations from November through May each year.  On our Virgin Islands Windjammer Cruises make yourself at home on our lovely sailing ship as we explore the US and British Virgin Islands.  We'll sail to a new island each day; you may enjoy a nap below decks as the water gently glides along our hull.

Where We Sail
On Deck
Vessel Specifications
Ships History

Cruising Grounds: The Virgin Islands

The Schooner Liberty Star offers crewed sailing charters in the Virgin Islands from our base at the East End of St. Thomas in the US Virgin Islands from Red Hook Harbor.  Each day we can sail to a new destination as we explore these enchanting islands from our tall ship.

Windjammer Liberty Star Sailing

Virgin Islands Windjammer Cruise Grounds

bvi map2
We offer week-long all-inclusive sailing cruises seasonally from November through May.  On your Virgin Islands Sailing charter, you'll have the opportunity to sail throughout both the US and British Virgin Islands.  We offer a very casual and relaxing sailing cruise; as such, we intentionally do not set up an itinerary for the week in advance.  This allows your sailing cruise to evolve so that we may sail with the best winds and see and the things you want each week!

Your Virgin Islands sail is likely to include visits to the following locations:

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!


  • St. Johns: 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


The Liberty Star: Accommodations

Liberty Star is a traditional gaff-rigged, two-masted wooden schooner, built by Maine craftsmen. The Liberty Star was lovingly refit for service in the British Virgin Islands in 2012 and features two upper and lower berth cabins, and a deluxe cabin with a full-sized double bed. All cabins offer opening skylights, and lots of varnished wood detailing. The below deck area is air conditioned.

Star Accommodations

The Cabins...

The cabins have been panelled in yellow-pine to provide a warm and rich feeling to our schooner. Each bunk is outfitted with comfortable pillows, linens, and blankets. We also provide both bath and beach towels.The cabins have 110-volt outlets to charge your camera and other electrical devices. Each bunk also has a reading light; just imagine reading yourself to sleep, after a wonderful home cooked meal, to the sound of the water lapping gently at the hull... You're sure to feel transported back to simpler days while on your sailing vacation cruise!

Cabins 1 and 2:

  • Our forward cabins offer top/bottom bunks with very comfortable beds. 
  • There is a "butterfly hatch" above each cabin to offer fresh air.
  • Each cabin has storage space in the custom-built storage lockers (please pack light, it is a tall ship!).
  • Each bunk has its own fan.

Cabin 1-2

Cabin 3:

  • Our deluxe cabin offers a full-sized bed.
  • This cabin also features an opening skylight for natural light and fresh air.
  • There is storage in the large cabin area and under bed storage.
  • This cabin features multiple fans.

Premium Cabin


There is one bathroom with a shower for our guests that is shared and we also have a fresh-water on-deck shower.

The Salon...

There is plenty of room at our table in the Salon or eat on deck under the warm caribbean sun.

Salon Breakfast

Liberty Star On Deck

The Tall Ship Liberty Star features a spacious open deck with lots of room to relax!  At 67-feet long, 76-feet tall and with a total beam (width) of 17-feet she's sized just right!  With just 6 guests and three crew aboard, you can always find a quiet place to yourself; even if that's out on the bowsprit...

Come discover the windjammer Liberty Star!


The Liberty Star: Specifications


Liberty Star was launched in 1982 by master shipbuilder George Emery after a ten-year construction period.  She was designed as a Gaff Topsail Schooner and can be fitted with a yardarm on her forward mast. The Liberty Star is a deep-water sailer that has completed a three-year circumnavigation.

Ship Registry

United States of America

Vessel Rig

Gaff Rigger Topsail Schooner


Boston, MA (Summer); Virgin Islands (Winter)

Length Overall


Length of Deck


Waterline Length






Mast Height




Sail Area

2,500 square feet

Gross Registered Tonnage


Vessel Displacement


Auxiliary Power

Cummins TurboDiesel 5.9L 210 H.P.


Oak and Mahogany


Douglass Fir and White Pine


Douglass Fir


Douglass Fir

Crew Compliment

3 Near-Coastal / 7 Offshore


George Emery

Year Built



United States Coast Guard Passenger Vessel


The Liberty Star: Safety

Liberty Star At Dock

Virgin Islands Sailing offers the only US-Flag and US-Crewed tall ship offering crewed sailing vacations in the Virgin Islands.  Your safety is always our number one priority, so rest assured that the Schooner Liberty Star exceeds all required United States Coast Guard Safety and Crew Training Requirements.  The Liberty Fleet is a company founded by professional sailors.  The Company's owner is himself a graduate of the Massachusetts Maritime Academy, holds an unlimited tonnage US Coast Guard license and understands and respects the unique demands of the sea upon both ships and crew.

Liberty Star Staffing:

A strong crew is always the most important aspect of any vessels safety program.  The Liberty Star's professional crew is fully licensed by the United States Coast Guard and led by our captains who are all highly qualified professional mariners with a minimum of 720-days of sea-going experience on similarly sized vessels; this typically reflects 4-5 years of industry experience.  Our Mate and Cook are also seasoned professionals that are there to provide for both your safety and comfort.

Safety Equipment:

Liberty Star is equipped with modern emergency communications equipment, emergency medical equipment and American Citizen crew-members who are trained in emergency response techniques.  Further, we have USCG inspected TYPE-1 Life Preservers, life-rings, a fully Coast Guard inspected fire-fighting system, and most importantly the training to effectively use this equipment.

What is the US Difference?

While all countries vessel registries have safety and inspection requirements, they are not all created equal.  Typically, European nations have a strong maritime tradition and maintain competitive safety standards with the United States.  Most non-US flag vessels, however, are registered under a “Flag of Convenience.”  Simply stated, this applies to those vessels under Panamanian, Monrovian, and other similar flags.  There are many reasons to register a ship under a foreign flag including: avoidance of taxes, avoidance of liability for injury, lower labor costs, and lack of inspection and safety oversight to save money.  Most developed nations maintain a watch-list for “flag of convenience vessels” visiting their territorial waters.

Other "yachts" available for charter are typically not inspected vessels and only carry whatever safety equipment their owners deem appropriate.  Further, those yachts are not subject to annual testing and inspections by any safety organization.  Aboard Liberty Star, you can sleep soundly knowing that the United States Coast Guard has fully inspected all aspects of our vessel.

Below is a list of some basic safety requirements and inspection requirements, see how things compare.

Safety Requirement

United States

Flag of Convenience Testing

Safety Inspection

USCG Annually

Typically “owner performed”

Hull Inspection

USCG Bi-Annually

Typically “owner performed”

Rig Inspection

USCG Bi-Annually

Never or “owner performed”

Crew Licensing

Strict: Experience & Testing

Pay for a License

Training Requirements

USCG Monthly Training

Typically “owner performed”

Liberty Star proudly flies a US Flag at her mast-head.  We take great pride in maintaining our ship to the highest safety standards and invite you to come sailing with us.



Our guests are serious about safety, too!

Safety At Bar



The Liberty Star: Vessel History

Liberty Star Heeled over

Liberty Star (Ex Rachel B. Jackson) was commissioned in 1972 in Harrington, Maine to be built as a private sailing yacht.  From 1972 to 1982, the vessel had three owners who each completed a portion of her construction.  In the early 1980s, a Maine shipwright named George Emery purchased the hull and completed the vessel in 1982.  She was originally christened the Rachel B. Jackson in honor of George Emery's grandmother, who had lent him the money necessary to purchase and complete construction on the schooner.
The vessel was built as a a working replica of an 1890s coastal schooner. Her sturdily built mahogany planking, oak frames, traditional pine and fir decking, shining brass fittings and exotic wood cabinetry recall the workmanship of days gone by.  The ship was originally put into service as a training vessel at Mystic Seaport in Mystic, CT.  In the mid 1980s, the Seaport sold the vessel to a private family who fitted her out and spent three years sailing her around the world on a circumnavigation voyage!  After completing her Round the World Voyage, the Schooner was sold to a family in Maine that operated her as a day-sail vessel and also showed her at Tall Ship Events.  She represented the State of Maine in the Tall Ships 2000 race from Bermuda to Boston then on to Halifax, NS. At one point, the vessel was chartered by the National Geographic Society to do whale research off the coast of the Dominican Republic.
In the spring of 2012, the Liberty Fleet found the Rachel B. Jackson "well-used" in Belfast, Maine and decided to save the ship.  On April 2, 2012, the Liberty purchased the vessel and on April 3, 2012 had a dumpster delivered to the shipyard and spent the next four months and 6,000 man-hours rebuiding the ship.  A partial list of work includes: new decking, re-caulking of the hull, replacing garboard strakes, partial refastening of the hull, installation of a new main-mast, repair of the fore mast, replacement of the main engine, drive shaft and propellor, new sails, new electronics and navigation equipment, installation of a new small boat, upgrades to wiring and plumbing systems and repainting of the entire hull.  Further, her interior was refit to include three staterooms for overnight accommodations and sailing in style!  The Liberty would like to recognize the three master shiprights that completed the refit: Mike Rogers, Geno Scalzo and Andros Kypragoras.
The Liberty felt that the original RBJ had given her all in life and decided to re-christen her Liberty Star.  Led by Captain Beau, the crew had an official renaming ceremony complete with a bottle of rum and a tot for Poseidon himself!
We now invite you to join us in sailing this beautiful vessel in the Caribbean on week-long Virgin Islands Sailing charters!
Welcome aboard!