Best results for
Sailing in Medford, MA
Showing 25-41 of 41 results
Boston Harbor Sail With Freshly Shucked Oysters
Sail Boston Harbor and enjoy freshly shucked oysters onboard
4.8 • 693 reviews
Sail Boston Harbor at Sunset on a Tall Ship
Watch the Boston skyline at twilight on a 2-hour tall ship sail
4.6 • 438 reviews
Historic Schooner Sunset Sail in Salem
Sunset sailing aboard John Alden's racing yacht
5.0 • 180 reviews
Celtic Music Sunset Schooner Sail on Gloucester Harbor
Sail into the sunset with live Celtic tunes and sea shanties
5.0 • 107 reviews
Sail Boston Harbor on a Tall Ship Day Cruise
Sail Boston Harbor on the Liberty Star tall ship in 1.5 hours
4.6 • 438 reviews
Private Sunset Sail in Salem
Charter a classic yacht for a relaxed Salem sunset sail
5.0 • 180 reviews
Heritage Day Schooner Sail in Gloucester Harbor
See visiting schooners up close during Gloucester's Heritage Day celebration
5.0 • 107 reviews
Greet the Fleet Sail at Gloucester Schooner Festival
Photograph visiting schooners as they arrive for Gloucester’s festival weekend
5.0 • 107 reviews
Gloucester Schooner Festival Private Sailing Charter
Sail in company with visiting schooners during Gloucester Schooner Festival Weekend
5.0 • 107 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
Salem 2-Hour Morning Mimosa Sail
Raise the sails and sip mimosas aboard a classic yacht on Salem Sound
5.0 • 180 reviews
Salem Sunday Bloody Mary Sail
Sail Salem Sound with Sunday Bloody Mary specials and hands-on sailing options
5.0 • 180 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