Best results for Sailing in Gloucester, MA
Showing 25-31 of 31 results
Salem Harbor Sunset Sail on 1812 Schooner
Watch Salem Sound glow at day’s end while you help raise the sails and toast the sunset with a relaxed drink.
5.0 • 534 reviews
Salem Sound Sail Aboard the Schooner Fame
Hands-on 1812-style sail with engaging crew and scenic Salem Sound views
5.0 • 534 reviews
2-Hour Historic Boston Harbor Sailing Cruise
Sail Boston Harbor with stories, skyline views, and complimentary pastries
4.6 • 438 reviews
2-Hour Boston Harbor Tall Ships Cruise
Cruise Boston Harbor for views of the tall ships on a classic schooner
4.6 • 438 reviews
Boston Harbor Sunset Tall Ships Sail
Sail Boston Harbor at sunset for views of the tall ships and skyline lights
4.6 • 438 reviews
Boston Harbor Sail With Freshly Shucked Oysters
Sail Boston Harbor and enjoy freshly shucked oysters onboard
4.8 • 693 reviews