Sailing in East Boston, MA

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

A private sunset outing aboard a historic schooner

Sail into the sunset with live Celtic tunes and sea shanties

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

Take the helm or relax aboard a historic wooden schooner

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

Charter a classic yacht for a relaxed Salem sunset sail

Sail Boston Harbor at sunset on a classic schooner

A private classic-yacht sail along the North Shore

Sail in company with visiting schooners during Gloucester Schooner Festival Weekend

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

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

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

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