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Top Boston Sailing Trips

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Boston to Martha's Vineyard Daytrip with optional Island Tour

Join Boston's only award winning, original, Martha's Vineyard Day Trip! Leave the trouble of driving to someone else and enjoy a day trip to Martha’s Vineyard from Boston. Rest and relax in a late model mini-coach on a 1.5-hour drive to the town of Falmouth, MA. Complimentary snacks, bottled water, island guidebooks and a discount card with island perks are provided during the drive.Then it’s on to the Island Queen ferry and a 35-minute mini-cruise across the waters of Vineyard Sound to Martha’s Vineyard. Upon arrival on the island, explore at leisure or upgrade to add a 3-hour island tour to the trip before returning.
  • Duration: 12 hours
  • Free Cancellation
  • Duration: 12 hours
  • Free Cancellation
From  
USD94.50
From  
USD94.50
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City Lights and Boston Skyline Harbor Sail

See Boston from a new perspective on an evening cruise through the harbor. As you take in rare views of the city skyline, your guide offers insight and stories about Boston’s history and historic landmarks, from Bunker Hill to the Tobin River Bridge. With drinks available for purchase and the option to bring your own food, the cruise is a popular choice for date nights, work events, and groups of visitors.
  • Duration: 1 hour 30 minutes
  • Duration: 1 hour 30 minutes
From  
USD42.00
From  
USD42.00
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Sightseeing Day Sail around Boston Harbor

Enjoy either a 1.5 or 2-hour sail around Boston Harbor aboard beautiful schooner Adirondack III, inspired by the pilot schooners of the 1890s. Sail past the seaport district, Castle Island, Fort Independence, Spectacle Island, and Long Island with Long Island Head Light. Great for families who want to sail and see the sights of Boston from the water!
  • Duration: 2 hours
  • Duration: 2 hours
From  
USD47.25
From  
USD47.25
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NEW TO VIATOR

Boston to Nantucket Daytrip with High-Speed Ferry

Enjoy a full day-trip excursion from Boston to Nantucket, a charming New England island deemed by National Geographic to be the "Best Island in the World." Start your day with an early morning pick-up aboard an air-conditioned Mini Coach Bus and sit back and relax during the hassle-free ride down to Hyannis. See panoramic ocean views during your 1-hour sail aboard the High-Speed ferry into Nantucket. With no traffic lights, no fast food restaurants and no highways, Nantucket's charm is evident upon arrival. You will have approximately 5 hours to explore the island at your leisure - from beaches to shopping and dining, there are options for everyone to enjoy. After a great day on Nantucket we will still have you back to Boston in time for a late dinner.
  • Duration: 12 hours
  • Free Cancellation
  • Duration: 12 hours
  • Free Cancellation
From  
USD159.00
From  
USD159.00
See Details


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(888) 651-9785
(888) 651-9785