Sailing Trips in Massachusetts
Top 10 Best Massachusetts Sailing Trips
Found 14 Sailing Trips activities in Massachusetts. Sort by Popularity.Sightseeing Day Sail around Boston Harbor
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... More
![Sightseeing Day Sail around Boston Harbor Sightseeing Day Sail around Boston Harbor](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/13/4a/17/26.jpg)
Sightseeing Day Sail around Boston Harbor
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Massachusetts
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Superb359 reviews4.7
Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....
Classic Tall Ship Sightseeing Cruise of Boston Harbor
Come out for a day sail adventure in Boston Harbor aboard our classic schooner, the Liberty Star. Get away from the hustle and bustle of the city streets and enjoy some quality time out on the water with unbeatable views of the ci... More
![Classic Tall Ship Sightseeing Cruise of Boston Harbor Classic Tall Ship Sightseeing Cruise of Boston Harbor](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/12/d7/14/78.jpg)
Classic Tall Ship Sightseeing Cruise of Boston Harbor
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Massachusetts
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Superb434 reviews4.7
Come out for a day sail adventure in Boston Harbor aboard our classic schooner, the Liberty Star. Ge....
Boston Harbor Sunset Sail Tour
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sailing experience will be aboard either Schooner Adirondack III or Adir... More
![Boston Harbor Sunset Sail Tour Boston Harbor Sunset Sail Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/10/74/8a/f3.jpg)
Boston Harbor Sunset Sail Tour
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Massachusetts
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Superb52 reviews4.6
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....
Sunset Sailing Cruise on a Tall Ship in Boston Harbor
If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic Boston tall ship! We depart Fan Pier Marina and raise the sails, then it’s time to just chill out and relax. Get a... More
![Sunset Sailing Cruise on a Tall Ship in Boston Harbor Sunset Sailing Cruise on a Tall Ship in Boston Harbor](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/12/d7/14/8d.jpg)
Sunset Sailing Cruise on a Tall Ship in Boston Harbor
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Massachusetts
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Superb363 reviews4.6
If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise....
Privateer Schooner Sailing Tour in Salem Sound
FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per TripAdvisor. Don't miss the very best of what Salem has to offer! There's more to our town than witches! FAME is a full-scale replica... More
![Privateer Schooner Sailing Tour in Salem Sound Privateer Schooner Sailing Tour in Salem Sound](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0b/2a/42/d2.jpg)
Privateer Schooner Sailing Tour in Salem Sound
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Massachusetts
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Superb491 reviews4.9
FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per Trip....
Sailing on Historic Schooner When And If in Salem, MA
Set Sail in beautiful Salem, Massachusetts on the schooner yacht When And If. The When And If was built in 1939 for the North Shore's own, General George Patton. Patton built the yacht with his famous quote as the intent "When the... More
![Sailing on Historic Schooner When And If in Salem, MA Sailing on Historic Schooner When And If in Salem, MA](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/06/74/83/96.jpg)
Sailing on Historic Schooner When And If in Salem, MA
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Massachusetts
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Superb108 reviews4.9
Set Sail in beautiful Salem, Massachusetts on the schooner yacht When And If. The When And If was bu....
2 Hour Sailing Tour of Vineyard Haven Harbor and Sound
Sailing is the best way to see and experience Vineyard Haven Harbor, Nantucket Sound and Vineyard Sound. Tandemeer is a big beautiful 1980 classic 60' ketch made famous in the 1982 hit movie "Trading Places" with Eddie Murphy, Dan... More
Private Tour
![2 Hour Sailing Tour of Vineyard Haven Harbor and Sound 2 Hour Sailing Tour of Vineyard Haven Harbor and Sound](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0c/06/1a/36.jpg)
2 Hour Sailing Tour of Vineyard Haven Harbor and Sound
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Massachusetts
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Superb7 reviews4.6
Sailing is the best way to see and experience Vineyard Haven Harbor, Nantucket Sound and Vineyard So....
Private Tour
Mimosas and Brunch in Boston Harbor
What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable views of the city. Your ticket includes complimentary coffee and fresh-baked pastries from the incomparable Flour Bakery + Cafe. F... More
Private Tour
![Mimosas and Brunch in Boston Harbor Mimosas and Brunch in Boston Harbor](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/12/d5/1c/8c.jpg)
Mimosas and Brunch in Boston Harbor
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Massachusetts
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Superb7 reviews5
What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable v....
Private Tour
3 Hour Sailing Tour of Vineyard Haven Harbor and Sound
Sailing is the best way to see and experience Vineyard Haven Harbor, Nantucket Sound and Vineyard Sound. Tandemeer is a big beautiful 1980 classic 60' ketch made famous in the 1982 hit movie "Trading Places" with Eddie Murphy, Dan... More
Private Tour
![3 Hour Sailing Tour of Vineyard Haven Harbor and Sound 3 Hour Sailing Tour of Vineyard Haven Harbor and Sound](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0b/22/7c/ee.jpg)
3 Hour Sailing Tour of Vineyard Haven Harbor and Sound
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Massachusetts
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Very Good4 reviews3.8
Sailing is the best way to see and experience Vineyard Haven Harbor, Nantucket Sound and Vineyard So....
Private Tour
4 Hour Sailing Tour of Vineyard Haven Harbor and Sound
Sailing is the best way to see and experience Vineyard Haven Harbor, Nantucket Sound and Vineyard Sound. Tandemeer is a big beautiful 1980 classic 60' ketch made famous in the 1982 hit movie "Trading Places" with Eddie Murphy, Dan... More
Private Tour
![4 Hour Sailing Tour of Vineyard Haven Harbor and Sound 4 Hour Sailing Tour of Vineyard Haven Harbor and Sound](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0b/cc/f6/ea.jpg)
4 Hour Sailing Tour of Vineyard Haven Harbor and Sound
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Massachusetts
Sailing is the best way to see and experience Vineyard Haven Harbor, Nantucket Sound and Vineyard So....
Private Tour
Spend the Day on Buzzards Bay - Sailing Trips
Skip the Newport bridge traffic and toursit traps and come spend the day in picturesque Mattapoisett Harbor, a quaint New England coastal village. Whether you want to go for a sail or cruise the shoreline, we're happy to make sug... More
Private Tour
![Spend the Day on Buzzards Bay - Sailing Trips Spend the Day on Buzzards Bay - Sailing Trips](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/12/e3/6c/80.jpg)
Spend the Day on Buzzards Bay - Sailing Trips
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Massachusetts
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Superb4 reviews5
Skip the Newport bridge traffic and toursit traps and come spend the day in picturesque Mattapoisett....
Private Tour
6 Hour Sailing Tour of Vineyard Haven Harbor and Sound
Sailing is the best way to see and experience Vineyard Haven Harbor, Nantucket Sound and Vineyard Sound. Tandemeer is a big beautiful 1980 classic 60' ketch made famous in the 1982 hit movie "Trading Places" with Eddie Murphy, Dan... More
Private Tour
![6 Hour Sailing Tour of Vineyard Haven Harbor and Sound 6 Hour Sailing Tour of Vineyard Haven Harbor and Sound](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0a/61/ec/e4.jpg)
6 Hour Sailing Tour of Vineyard Haven Harbor and Sound
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Massachusetts
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Superb2 reviews5
Sailing is the best way to see and experience Vineyard Haven Harbor, Nantucket Sound and Vineyard So....
Private Tour
Private Charter Day Sail For up to 6 People
Set sail in Beautiful Salem sound on your very own private sailing charter! When purchasing, you will get a private sailing trip for up to 6 people on the beautiful classic sailboat Wenonah. An hour and a half harbor day sail is t... More
Private Tour
![Private Charter Day Sail For up to 6 People Private Charter Day Sail For up to 6 People](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/06/74/83/98.jpg)
Private Charter Day Sail For up to 6 People
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Massachusetts
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Superb7 reviews5
Set sail in Beautiful Salem sound on your very own private sailing charter! When purchasing, you wil....
Private Tour
Spend the Day on Buzzards Bay - Powerboat Cruises
Embark on an unforgettable journey aboard our private powerboat "Petrel" Pricing is just $375 per hour for a two-hour trip. Up to 6 passengers are welcome aboard. Whether you crave adventure, relaxation, or both, our charters prom... More
Private Tour
![Spend the Day on Buzzards Bay - Powerboat Cruises Spend the Day on Buzzards Bay - Powerboat Cruises](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/13/46/e1/07.jpg)
Spend the Day on Buzzards Bay - Powerboat Cruises
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Massachusetts
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Superb1 review5
Embark on an unforgettable journey aboard our private powerboat "Petrel" Pricing is just $375 per ho....
Private Tour