9 Boston Sailing Tours to Get on the Water

1.Classic Tall Ship Cruise in Boston Harbor

★★★★★★★★★★4.5 · 615 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $35Our pick

Board Liberty Fleet of Tall Ships at Marina Overlook for a 90-minute sail aboard the Liberty Star. Captain Fredo and crew may invite you to help raise the sails while sharing harbor commentary. Bring a bagged lunch, buy drinks onboard, and enjoy skyline and Constitution views from the water.

“I enjoyed it. even go to help pull up the main sail!! Would love to do it again, actually go to get involved and do some of the tasks.”

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2.Sightseeing Day Sail around Boston Harbor

★★★★★★★★★★5.0 · 541 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $66Top rated

Sail Boston Harbor aboard Schooner Adirondack III or IV for 1.5 or 2 hours. You’ll pass the Seaport District, Fan Pier, Castle Island, Fort Independence, Spectacle Island, and Long Island. The crew answers questions, drinks are sold by card, and the boat often sails under wind power rather than engine power.

“We learned some history and some local spots from the water. We also got some tips for restaurants and activities in the area. Good experience and beautiful views from the boat”

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

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

Board at Fan Pier Marina for a two-hour sunset sail aboard a classic Boston tall ship, often the Liberty Star. Expect skyline and harbor views, a relaxed crew, drinks and snacks for purchase, and possibly a chance to help with the sails. Capt. Fredo, Jess, and Max have worked some recent departures.

“The crew was fantastic. The views were amazing and drinks were good. Everyone onboard was having a great time. If you have never been on a tall ship this is a nice experience.”

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4.Harbor Champagne Sunset Sail from Rowes Wharf

★★★★★★★★★★4.8 · 299 reviews · 2 hours · from $82

Spend two hours sailing Boston Harbor aboard Schooner Adirondack III or IV from Rowes Wharf. You’ll see the Fish Pier, Castle Island, Charleston Navy Yard, and the skyline while crew members such as Steve or Therese may share local stories. Bring a picnic, buy drinks by credit card, and dress warmly for the cool water.

“The sailboat cruise was a lot of fun. The captain and staff were personable and engaged with the guests. Chocolate cookies are good! The weather was colder than expected, and souvenir blankets were available for purchase, which was great, too.”

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5.Tall Ship Harbor Sail

★★★★★★★★★★4.6 · 261 reviews · 1h 30m · from $35

Step aboard a classic Liberty Fleet schooner at Fan Pier Marina for a 90-minute Boston Harbor sail. You can help raise the sails, ask the captain about landmarks, and buy Boston-brewed beer, wine, or cocktails onboard. Expect a relaxed outing with skyline views, but no formal narration and possible motor use when the wind is light.

“Lots of fun for my family celebrating my husband's 75th birthday.”

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6.Downtown Harbor Sailing Cruise

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

Board the classic Adirondack III or IV for a 90-minute or two-hour sail around Boston Harbor. The crew points out the Aquarium, Moakley Courthouse, Castle Island, the Navy Yard, and harbor islands. Bring a picnic, buy a drink by card, and enjoy a close-to-the-water view of Boston.

“I’ve long seen pictures of the ships with big sails raised. Now I have had the experience of sailing on one! Loved feeling the wind in my hair and watching the wind fill the sails that carried us across the water!”

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7.Boston Harbor Sunset Sail Tour

★★★★★★★★★★5.0 · 132 reviews · 2 hours (approx.) · from $82

Spend about two hours sailing Boston Harbor aboard the schooner Adirondack II or III. You will pass the Seaport District, Fan Pier, harbor islands, Castle Island, and Fort Independence while the city lights come on. This is not a narrated cruise, but crew members such as Dante, Charlie, and Claire are on hand to answer questions and serve drinks.

“A beautiful night. The sail was wonderful, though it felt a little crowded for seating, but the staff were fun and engaging and we got beautiful photos of the sunset on the Boston Harbor.”

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8.Sunset Tall Ship Harbor Cruise

★★★★★★★★★★4.8 · 115 reviews · 2 hours · from $68

Join Liberty Fleet of Tall Ships for a two-hour sunset sail from Fan Pier Marina. Help raise the sails, ask the crew about Boston landmarks, and enjoy views from the water. Captains and crew, including Freido, Jess, Max, and Jonathan, are known for making the trip friendly and hands-on. Drinks are available for purchase, but bring your own snacks.

“We had a really great time! The staff were very friendly we enjoyed it very much.”

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9.Sunday Pastry & Prosecco Sail on Boston Harbor

★★★★★★★★★★5.0 · 8 reviews · 2 hours · from $75

Board the schooner Liberty Star at Fan Pier for a two-hour Sunday sail with fresh Flour Bakery pastries, coffee, and tea. The crew may invite you to help with the sails, and you can ask the captain about Boston landmarks. Mimosas and other drinks are available onboard, with no formal narration.

“This was a thoroughly enjoyable sail. The Captain and crew (especially Freddo) were fun and easy going. I got to help Freddo hoist the topsail. The many pastries that made up the brunch were all fresh. The mimosas were cheap, plentiful and made island strength! I highly recommend this cruise and bunch of people.”

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