8 Sailing Trips in Boston Worth Booking

1.Schooner Fame Sailing Tour

★★★★★★★★★★5.0 · 571 reviews · 1 hour 40 minutes (approx.) · from $50.65Our pick

Sail Salem Sound on the replica schooner Fame. Hoist sails, steer a bit, hear privateer stories, and enjoy views from Pickering Wharf.

“It was awesome! Beautiful day and smooth sailing! Captain was great and his mates were as well! Truly a wonderful experience !”

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2.Harbor Sunset Yacht Cruise

★★★★★★★★★★4.6 · 570 reviews · 2 hours · from $54

A 2-hour Boston Harbor sunset cruise on the Northern Lights yacht, with music, light commentary, and cannon fire off USS Constitution.

“Fantastic boat, friendly crew and wonderful trip - all round, would definitely recommend.”

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3.Sunset Sailing Cruise on a Tall Ship in Boston Harbor

★★★★★★★★★★4.5 · 414 reviews · 2 hours (approx.) · from $68

Cruise Boston Harbor at sunset on a classic tall ship. Enjoy skyline views, friendly crew, and purchase drinks and snacks onboard.

“There was no narrator and no music. The captain said that he did not know any of the surrounding sites.”

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4.Downtown Harbor Sailing Cruise

★★★★★★★★★★4.8 · 227 reviews · 90 minutes - 2 hours · from $66

Sail past Boston’s waterfront on a classic schooner, feel the wind, learn the landmarks from a friendly crew, and buy drinks onboard.

“It's hard to pick one thing. The crew were super nice, the boat was in beautiful shape, clean etc. The overall experience of being in such a big sail boat, seeing the crew raise the sails in an orderly fashion, feeling the angle of the ship as we were sailing into the wind, looking up at those beautiful sails on those tall masts against the blue sky, the very different feel on the way back with wind behind us, then finally lowering the sails and expertly steering this beast into its spot, for me it was just a wonderful experience. The crew were a big part of the reason for…”

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5.Sailing on Historic Schooner Yacht in Salem, MA

★★★★★★★★★★5.0 · 172 reviews · 2 hours (approx.)

2-hour Salem Sound sunset sail on a restored schooner, help hoist sails, pass Marblehead, and sip drinks on board.

“The crew is extremely knowledgeable and answers all your questions and is excited to tell you about the history of the beautiful vessel. This is an absolutely must do when in Salem”

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6.Historic Schooner Sailing Cruise

★★★★★★★★★★4.9 · 84 reviews · from $39Best value

Sail the historic schooner Fame from downtown Salem for 100 minutes of hands-on sailing, scenery, and drinks on board.

“Perfect, great day for sailing. Our guides were wonderful and included everyone in the journey and experience. It was a lot of fun and knowledge was shared”

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7.Boston Harbor Private Sunset & Foliage Cruise, on Yacht Trinacria

★★★★★★★★★★5.0 · 1 reviews · 2 hours (approx.) · from $1,200

Private Boston Harbor sunset cruise on Yacht Trinacria for up to 6 people, with skyline and bridge views plus free soft drinks in English.

“The sunset cruise was incredible and serene. Boat was clean and comfortable, and Captain Riccardo was knowledgeable and accommodating!”

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8.Cruise – Sightsee – Foliage in Boston, on Private Yacht Trinacria

★★★★★★★★★★5.0 · 1 reviews · 3 to 5 hours (approx.) · from $2,000

Private yacht cruise around Boston’s waterfront with photo stops at USS Constitution, Bunker Hill, Boston Light, plus fishing gear included.

“Captain Riccardo is a true professional in every sense of the word. From the history of Boston to knowing right where the best spots were to fish. We had an amazing day and will be back. I highly recommend. Captain Riccardo will not disappoint.”

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