Sailing in Oak Bluffs, MA

Feel the power of sailing on Martha's Vineyard waters

Sail Vineyard Sound with lighthouse views and secluded swim options

Relax on deck as the sun sets over the water

Sail Martha's Vineyard aboard a historic 1926 schooner

Build sailing skills with a private youth lesson for up to 3 sailors

Set sail on a private classic sloop tailored to your group

Catch the bay breeze past New Bedford's working waterfront

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

Build sailing skills with private coaching tailored to your goals

Explore JAWS movie history with shark-themed drinks and trivia

Sail close to the water on an interactive harbor charter

Help your toddler build confidence on the water with an instructor-led sailing introduction

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

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

Build sailing confidence with instruction tailored to your experience

Refine your sailing technique and build confidence on the water