Sailing in Kingston, MA

Sail New Bedford Harbor and Buzzards Bay on a private charter

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

Take in Boston's waterfront from a sailboat reserved for your group

Sail close to the water on an interactive harbor charter

Take the helm and discover sailing aboard a traditional cutter ketch

Tailor a hands-on sail to the skills you want to sharpen

Step ashore on quiet harbor islands while your captain waits

Sail Cape Cod Bay on the historic Schooner Hindu

Learn to design, build, and repair sails in a hands-on two-day class

Catch the bay breeze past New Bedford's working waterfront

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

Sail Provincetown at sunset on the historic Schooner Hindu

Sail Boston Harbor at sunset on a classic schooner

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

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

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

Sail Cape Cod Bay on a family-friendly cruise where you can help raise sails and bring a picnic aboard

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

Watch Provincetown’s shoreline glow from a classic Victorian yacht

Charter a private sail in Provincetown for up to 34 guests

Sail Boston during Sail Boston 2026 on the restored Schooner Hindu

Private classic schooner sail with lighthouse and cove views