Under sail · BOSTON SAILING TOURS
Sunset runs, swim stops and full days at anchor. These 4 are the sails in Boston worth the booking, compared on the details that matter once you are aboard.
Board the Liberty Star at Marina Overlook for a 90-minute Boston Harbor sail. Captain Fredo and crew may invite you to help raise the sails, while you enjoy skyline views, fresh air, snacks, and drinks, including South Boston beer. Bring a bagged lunch, but do not expect a fully narrated harbor tour.
“Beautiful views of Boston. Such a different experience from the water. The crew was great. Loved it!”
Board the Adirondack III or IV at Rowes Wharf for a relaxed Boston Harbor sail. You’ll pass the Seaport District, Fan Pier, Fort Independence, Spectacle Island, and Long Island. This is not a fully narrated cruise, but the captain and crew answer questions. Bring a snack, dress warmly, and buy drinks by card.
“Fun and relaxing experience. We had a very good time. The captain was very friendly and courteous....”
Spend about two hours aboard a Liberty Fleet tall ship, sailing from Fan Pier Marina around Boston Harbor at sunset. Expect skyline and island views, a relaxed crew, drinks and snacks for purchase, and occasional chances to help with the sails. Captains and crew members may vary, with Captain Fredo, Jess, and Max among the crew praised for making the trip fun.
“We had a wonderful time on the sunset cruise! The crew was very knowledgeable and kind. They were very attentive with refilling drinks! We would definitely do this again the next time we are in the Boston area! Highly recommend!”
Spend two hours sailing Boston Harbor aboard Schooner Adirondack III or IV. From Rowes Wharf, you’ll pass the Fish Pier, Fan Pier, Castle Island, the Inner Harbor Islands, and Charlestown Navy Yard as the city turns gold. The crew, including hosts such as Steve or Therese on some sailings, shares local history while drinks are available to buy onboard.
“This sunset champagne cruise was lovely! The crew was attentive and professional and the sunset views of the city were incredible. I would definitely highly recommend this activity!”
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