Best results for
Sailing in Chestnut Hill, MA
Showing 25-34 of 34 results
Historic Schooner Sunset Sail in Salem
Sunset sailing aboard John Alden's racing yacht
5.0 • 180 reviews
Full-Day Private Sailing Charter & Island Tour in Boston
Step ashore on quiet harbor islands while your captain waits
4.8 • 23 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
Salem 2-Hour Morning Mimosa Sail
Raise the sails and sip mimosas aboard a classic yacht on Salem Sound
5.0 • 180 reviews
2-Hour Historic Boston Harbor Sailing Cruise
Sail Boston Harbor with stories, skyline views, and complimentary pastries
4.6 • 438 reviews
Salem Sunday Bloody Mary Sail
Sail Salem Sound with Sunday Bloody Mary specials and hands-on sailing options
5.0 • 180 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