Sailing in Bourne, MA

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

Sail Martha's Vineyard aboard a historic 1926 schooner

Sail Cape Cod Bay on the historic Schooner Hindu

Set sail on a private classic sloop tailored to your group

Catch the bay breeze past New Bedford's working waterfront

Feel the power of sailing on Martha's Vineyard waters

Sail Provincetown at sunset on the historic Schooner Hindu

Share an evening harbor sail as the light shifts over the water

Raise the sails or take the wheel on Martha's Vineyard waters

Sail New Bedford Harbor and Buzzards Bay on a private charter

Sail Vineyard Sound with lighthouse views and secluded swim options

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Explore JAWS movie history with shark-themed drinks and trivia

Sail close to the water on an interactive harbor charter

Relax on deck as the sun sets over the water

Sail Vineyard Haven Harbor with brunch bites, mimosas, and live jazz

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

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