Best results for Sailing in Nantucket, MA

Set sail on a private classic sloop tailored to your group

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

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

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

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

Raise the sails or take the wheel aboard a historic schooner

Learn sailing fundamentals with private on-water instruction

A private evening sail with room for your own refreshments

Set sail privately with your group on Pleasant Bay

Take the helm of a forgiving catamaran for easy bay sailing

Build sailing skills with private coaching tailored to your goals

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

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

Build sailing confidence with instruction tailored to your experience

Refine your sailing technique and build confidence on the water

Explore JAWS movie history with shark-themed drinks and trivia