Sailing in Charlestown, MA

Sail Boston Harbor and enjoy freshly shucked oysters onboard

Sunset sailing aboard John Alden's racing yacht

Step ashore on quiet harbor islands while your captain waits

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

A private sunset outing aboard a historic schooner

Sail into the sunset with live Celtic tunes and sea shanties

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

Sail Boston Harbor at sunset on a classic schooner

A private classic-yacht sail along the North Shore

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

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

Raise the sails and sip mimosas aboard a classic yacht on Salem Sound

Sail in company with visiting schooners during Gloucester Schooner Festival Weekend

Sail Salem Sound with Sunday Bloody Mary specials and hands-on sailing options

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