Island Water Sports: Where to Paddle, Sail, Flyboard, and more on Martha’s Vineyard

If your ferry ride is the only time you spend on the water while visiting Martha’s Vineyard, you’re missing out. Practically every water sport you can think of—from the traditional to the new and exotic—is available on these shores. We’ve rounded up our favorite island water sports below, with tips on where to rent gear and get your feet wet.

Island Water Sports Near Edgartown

For island water sports that take a bit of practice, like stand-up paddleboarding, the sheltered flat waters of Sengekontacket Pond and Majors Cove are a perfect place to play. Inland from the sparkling sands of Joseph Sylvia Beach (that’s State Beach to islanders), you can’t miss this area as you cross the Jaws Bridge halfway between Edgartown and Oak Bluffs. We recommend Island Spirit Kayak in Oak Bluffs for kayaks and paddleboards. They’re conveniently located right on an inlet between the beach and the pond, so you can choose to explore the coastline or take it easier inland.

Further up the road, on Oak Bluffs Harbor, Martha’s Vineyard Oceansports offers a full array of motorized island water sports at surprisingly reasonable rates. This is the spot to rent a jet ski or go parasailing. MV Oceansports is also one of very few shops in the northeastern US to offer flyboarding. If you haven’t heard of this sport, imagine wakeboarding 15 feet up in the air. It’s not as scary as it sounds and it’s surprisingly easy to get the hang of. Instructors Kevin and Gene became some of the first pros at this island water sport when it was invented in the early 2010s, so you’ll be in good hands if you give it a go.

Both of these island water sports shops are easily accessible by Vineyard Transit Authority bus during the warmer months.

Up-Island Water Sports

If you want to hang ten on the west coast—of Martha’s Vineyard, that is—take a day trip up-island and visit either Aloha Paddle in Aquinnah or Book-a-Boat in Menemsha. Though it’s a bit further away from Edgartown, you’ll share these waters with fewer fellow paddlers and take in views you can’t find anywhere else.

Aloha is 100% stand-up paddleboarding, with lessons, tours, and rentals available daily. Their kids’ programs make planning a family outing easy. Already got some experience? Challenge yourself with a SUP yoga class or paddle out on the open water to see the famous Gay Head cliffs from a totally new point-of-view.

Want to try your luck with the rod and reel without hiring a Martha’s Vineyard fishing charter? Book-a-Boat has a full selection of sailboats, sunfish, and motorized fishing boats, with kayaks and paddleboards available as well. Like their hometown of Menemsha, Book-a-Boat is a little old-fashioned—they prefer to make reservations over the phone to ensure you get exactly what you’re looking for.

Island Water Sports in Vineyard Haven

In the middle of the island’s north shore, where the Steamship Authority ferries come and go like clockwork, Vineyard Haven’s Wind’s Up natural watersports shop doubles as a great place to pick up forgotten essentials: they stock high-quality bathing suits, sunglasses, hats, and other supplies along with their rental fleet of kayaks, canoes, SUPs, and surfboards. This is an easy place to pick up rentals on your way to Edgartown from the ferry—just tell your taxi driver to take the scenic route (Beach Road, which is well worth the extra few minutes for its ocean views) and stop on the way.

After you explore Martha’s Vineyard by water, you’ll need a cozy place to stay on land—all of us at Vineyard Square, in the heart of downtown Edgartown, would love to welcome you and help plan your adventures.