Sailing in South Dennis, MA

A private evening sail with room for your own refreshments

Set sail privately with your group on Pleasant Bay

Sail Martha's Vineyard aboard a historic 1926 schooner

Sail Cape Cod Bay on the historic Schooner Hindu

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

Learn sailing fundamentals with private on-water instruction

Set sail on a private classic sloop tailored to your group

Sail Provincetown at sunset on the historic Schooner Hindu

Take the helm of a forgiving catamaran for easy bay sailing

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

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

Build sailing skills with private coaching tailored to your goals

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Explore JAWS movie history with shark-themed drinks and trivia

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

Build sailing confidence with instruction tailored to your experience

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

Refine your sailing technique and build confidence on the water

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