Chappy Charters was founded from a lifelong love of Martha’s Vineyard and the unforgettable moments that happen on the water. Some of my most cherished memories — from sailing camp and tubing wipeouts to lobster bakes on Wasque — were made right here, and they’ve shaped how I see the island, nature, and life.

Chappy Charters’ mission is simple: to help create lasting memories from the moment you step on board. Whether you’re a group of friends looking for a laid-back cocktail cruise or a family eager for a new kind of island adventure, we offer a personalized way to experience the Vineyard — from a whole new perspective.

Join me, and let the water be the backdrop to your next great Vineyard story.