Best results for Sailing in Boston, MA

Cruise Boston Harbor on a 1.5- or 2-hour schooner day sail

Sail Boston Harbor at sunset on an 80-foot schooner

Weekend brunch sail on Boston Harbor with pastries, coffee, and tea

Watch the Boston skyline at twilight on a 2-hour tall ship sail

Sail Boston Harbor on the Liberty Star tall ship in 1.5 hours

Sail Boston Harbor at sunset on a classic schooner

Private sail for up to 6 guests beyond Marblehead Harbor

Private 4-hour sail from Marblehead Harbor for up to 6 guests

Private sailing with coastal views along Boston's North Shore

Sail a 1930 schooner past Salem Sound lighthouses

Make Salem Sound your private escape aboard a classic schooner

Sunset sailing aboard John Alden's racing yacht

A private sunset outing aboard a historic schooner

Take the helm or relax aboard a historic wooden schooner

Sail Salem’s North Shore aboard a storied 1939 wooden schooner

Sail historic harbor waters with maritime insights and optional hands-on sailing

See visiting schooners up close during Gloucester's Heritage Day celebration

Photograph visiting schooners as they arrive for Gloucester’s festival weekend

Sail Boston Harbor and enjoy freshly shucked oysters onboard

Sail Boston Harbor with stories, skyline views, and complimentary pastries

Cruise Boston Harbor for views of the tall ships on a classic schooner

Sail Boston Harbor at sunset for views of the tall ships and skyline lights

Watch Salem Sound glow at day’s end while you help raise the sails and toast the sunset with a relaxed drink.

Hands-on 1812-style sail with engaging crew and scenic Salem Sound views