Sailing in Mashpee, MA

A private evening sail with room for your own refreshments

Catch the bay breeze past New Bedford's working waterfront

Feel the power of sailing on Martha's Vineyard waters

Set sail privately with your group on Pleasant Bay

Sail New Bedford Harbor and Buzzards Bay on a private charter

Sail Vineyard Sound with lighthouse views and secluded swim options

Take the helm of a forgiving catamaran for easy bay sailing

Sail close to the water on an interactive harbor charter

Relax on deck as the sun sets over the water

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

Sail Martha's Vineyard aboard a historic 1926 schooner

Learn sailing fundamentals with private on-water instruction

Set sail on a private classic sloop tailored to your group

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

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

Explore JAWS movie history with shark-themed drinks and trivia

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