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 itself.

The Chappy Charters mission is simple: to help you 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 to discover the island’s hidden gems, we offer a unique and personalized way to experience the Vineyard—from a whole new perspective.

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