Sailing in Winthrop, MA

Reserve a traditional schooner for your celebration on Gloucester Harbor

Sail Boston Harbor at sunset on a classic schooner

Private schooner sailing with captain and crew included

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

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

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

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

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 in company with visiting schooners during Gloucester Schooner Festival Weekend