On the Water

Island Spirit Kayak


9:00AM - 3:00PM

Specializing in providing kayak and SUP (Stand Up Paddle Board) tours. Their goal is to introduce the natural beauty of these islands through low impact observation while providing a fun and safe activity.

State Beach

(508) 693-9727


MV Ocean Sports


8:00AM - 8:00PM

Martha’s Vineyard’s premier oceansports company offering everything to make your watersports experience memorable.

Dockside Marina
(508) 693-8476


Oak Bluffs Marina


8:00AM - 8:00PM

As the largest marina on Martha's Vineyard, Oak Bluffs Marina not only has the most slips, but is situated right next to the historic Camp Meeting Association’s gingerbread cottages, and offers easy access to the rest of the Island.

At the Oak Bluffs Harbor
Circuit Ave. Extension.



Pirate Adventures


Various times

A custom-made 40-foot vessel is designed just for kids! The Sea Gypsy is it’s a stage at sea - a safe, magical place for imagination to take over and memories to be made. From beginning to end, the action is non-stop as they transform your kids into a hearty pirate crew. Every new mate gets a pirate name, face-paint, dresses up and learns how to talk like a pirate - all before they leave the shore!

Dockside Marina
(508) 687-2739

Sea Witch Sailing Charters


Various times

Set sail with Sea Witch Sailing Charters and see for yourself why life is better at sea.  Bask in the sea breezes and warm sun, unplug from the stress and rush of daily life, and live the dream for an afternoon, a day or a week.  With the wind in your hair and the warmth of the sun on your skin, you’ll get bewitched by the magic of the sea aboard our sailing yacht.

10 Circuit Ave Ext
(508) 650-0466

Vineyard Sound Charters


8:00AM - 5:00PM

Martha's Vineyard's most popular fishing boat, the Skipper, offers a unique ocean fishing experience on the protected and calm waters of the Vineyard Sound.


She is centrally located in the town of Oak Bluffs for easy access from all points of the island.

Oak Bluffs Harbor
(508) 326-8857

Winds Up!


9:00AM - 6:00PM

Wind's Up is Martha's Vineyard's headquarters for natural water sports: Stand Up Paddle boards, kayaks, sailboats, canoes, windsurfers, surf & beach clothing/gear, lessons and sales/rentals. Stop by our shop, located on 199 Beach Rd, Vineyard Haven, to get your beach gear, rent one of our kayaks or take a windsurfing or sailing lesson. Have fun this summer, stop by Wind's Up.

On the Lagoon in Tisbury
(508) 693-4252

The Oak Bluffs Association

Email: oakbluffsassociation@gmail.com

Christine Todd, Executive Director

PO Box 1521,

Oak Bluffs, MA 02557

Phone: 774-563-9197

Subscribe to Our Newsletter
Quick Links

© 2023 by The Oak Bluffs Association. Proudly created with Wix.comTerms of Use  |   Privacy Policy