Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle Island, Fort Independence, Spectacle Island, and Long Island with Long Island Head Light. Great for families and friends who want to sail and see the sights of Boston from the water!
Within minutes of leaving the dock, guests will forget the distractions of life on land and experience the joy of a leisurely sail. Sit back and relax as the crew raises sail and provides beverage service. Drinks are available for purchase by credit card only. Guests are welcome to bring a picnic onboard.
The knowledgeable captain and crew are always ready to answer questions about the sights and history of Boston Harbor and its surrounding areas. From interesting facts to old-time legends, the maritime world of Boston has many great stories to offer.
Posted By : Yuri_K
It was a wonderful sail, well organized, everything was as advertised. I loved the trip, and I would do it again.
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Posted On : 2024-07-05 19:58:47 
Posted By : Beth_D
It was great to see Boston from the water with a knowledgeable and experienced crew! My 3 teens loved the experience. Everyone involved was great. It was definitely worth the money!
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Posted On : 2024-07-05 16:01:46
Posted By : AnnRuth_L
I loved the boat ride. The captain and his mates were very welcoming and it was a
great time!! The weather was perfect and I can’t say enough about it.
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Posted On : 2024-07-05 12:47:33
Posted By : Ellen_M
Lovely sailing on the 4th. Wonderful boat, crew, and captain. Highly recommended for those who don't want to go on a booze cruise.
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Posted On : 2024-07-05 09:35:47
Posted By : Leapclw
This was a lovely, smaller tour. Crew was professional, attentive, and pleasant. It was a really nice day on the water…We all enjoyed it!
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Posted On : 2024-07-05 09:13:29 
Posted By : Odyssey33230210500
The crew was very knowledgeable, beautiful cruise around the islands and great staff, captain, and excellent service! Don't miss the Sunset cruise!
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Posted On : 2024-07-04 20:23:00
Posted By : Anonymous
It was a very busy harbor. Did not go very far in distance. Stayed in the inner harbor. Very friendly crew.
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Posted On : 2024-07-04 11:17:49
Posted By : Christine_B
This was a very good sail boat ride, I wished as they were sailing that they would have told us about the area. I understand that it says we are supposed to ask they, just saying it would be nice I will have to tell everyone that is thinking about going sailing with this company, go ahead it was great!
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Posted On : 2024-07-03 19:07:34
Posted By : Amy_B
The crew was friendly, knowledgeable, and attentive. We liked the laidback feel of the trip. We had an excellent time!
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Posted On : 2024-06-29 12:08:20
Posted By : Sandro_L
All good, professional and capable crew.
Nice breeze in the bay.
I would have loved to help in maneuvering but I was not allowed ☹️
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Posted On : 2024-06-26 14:38:57
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