Sailing Trips in Massachusetts
Top 10 Best Massachusetts Sailing Trips
Found 9 Sailing Trips activities in Massachusetts. Sort by Popularity.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
Likely to Sell Out Boston Harbor Sunset Sail Tour
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Massachusetts
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Superb62 reviews4.7
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront ....
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
Likely to Sell Out Classic Tall Ship Sightseeing Cruise of Boston Harbor
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Massachusetts
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Superb454 reviews4.7
Come out for a day sail adventure in Boston Harbor aboard our classic schooner, the Liberty Star. Ge....
Sailing on Historic Schooner Yacht in Salem, MA
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X. Winner of the 1930 and 1932 Newport to Bermuda race and open... More
Likely to Sell Out Sailing on Historic Schooner Yacht in Salem, MA
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Massachusetts
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Superb124 reviews4.9
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience ....
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
Likely to Sell Out Sightseeing Day Sail around Boston Harbor
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Massachusetts
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Superb382 reviews4.7
Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner....
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
Likely to Sell Out Sunset Sailing Cruise on a Tall Ship in Boston Harbor
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Massachusetts
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Superb376 reviews4.6
If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise....
Schooner Fame Sailing Tour
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
Likely to Sell Out Schooner Fame Sailing Tour
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Massachusetts
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Superb524 reviews4.9
FAME is annually the #1-rated boat in Salem and the #1 outdoor activity in the entire town, per Trip....
Pastries and Prosecco 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
Likely to Sell Out Pastries and Prosecco 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....
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
Likely to Sell Out Spend the Day on Buzzards Bay - Sailing Trips
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Massachusetts
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Superb6 reviews5
Skip the Newport bridge traffic and toursit traps and come spend the day in picturesque Mattapoisett....
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
Likely to Sell Out 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