Scratching That Schooner Sailing Itch

If you were lucky enough to make it to Baltimore, Annapolis, Portsmouth, VA, or somewhere in between during the Great Chesapeake Bay Schooner Race (October 12-16), you may have spotted the 125-foot, gaff-rigged Schooner Liberty Clipper. You may have seen her port of call of Boston, MA, or have looked her up online to learn her captain’s name: Andy Huntoon.

Surely a few Virginia sailors noted that she did not head for Boston after the Sunday awards brunch; she headed south to find some palm trees and sandy beaches. If you wished you could hop onboard for a ride, your wish could come true.

The Liberty Clipper is one of two ships in the Liberty Fleet of Tall Ships, a 23-year-old, family-owned, Boston-based company that runs charters out of Boston, offshore passages, and windjammer cruises in the Bahamas and Virgin Islands. The Clipper’s 12 cabins can accommodate 24 passengers, whereas its sister ship, the 60-foot, gaff-rigged Schooner Liberty Star, accommodates six.

If you seek a bluewater adventure, at print time, there were spots for the December 4-10 Jacksonville, FL, to Nassau trip. Come spring, there will be two northbound passage opportunities, all spelled out on the Liberty Fleet website ( 

If the Bahamas sound appealing to you, that’s where you can book a three- to six-day cruise starting in Nassau and exploring the Bahamas, weekly from December through May. 

“Each trip is somewhat customized according to weather and local events,” says cruise coordinator Dennis LaKomski. “We might start at Eleuthera and then go down to the Exumas. Then the next week, it will probably be a bit different… Because we’re small, we are able to build off what people liked each trip.” 

LaKomski enjoys the wide variety of people who sign on for such an adventure, ranging from young couples in search of interesting honeymoons, families traveling with teenagers (the age limit is 10 years old), or a group of friends having reunions or celebrating big birthdays. The boat accommodates 24, including paid deckhands, cooks, the captain, and a first mate. For those traveling as singles, there are gender-specific single bunks available. The per-person cost is $1299 with upgrades available.

Anyone who knows the Bahamas knows the joys of playing in small boats at anchorages, and the Liberty Clipper crew is prepared with water toys: snorkel and fishing gear, kayaks, paddleboards, and a sailing dinghy. 

If you have a group of three couples or six friends, perhaps the Liberty Star cruise in the U.S. and British Virgin Islands is for you. The cost is $1450, with upgrades available. Trips depart from St. John and as with the Bahamian trips, go where weather and local events best suit the guests. As with the other trips, you may also book as a single (open spots are clearly marked on the website).

According to LaKomski, about a third of the Liberty Clipper and Star guests return for tropical and New England adventures alike. 

“We like to create an atmosphere of our guests feeling like a part of the family.”

To learn more, visit If you book a trip, make sure to let the crew know that you read about it in SpinSheet!