Best 170 things to do in Oak Bluffs, MA

Try four tow sports with professional instruction on the water

Take your group out on a 17-foot Boston Whaler

A fishing-ready center console with rod holders and a live well

Take the helm of a 19-foot center console with fishing-ready features

Explore Martha’s Vineyard waters with your group

Set sail on a private classic sloop tailored to your group

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

Explore JAWS movie history with shark-themed drinks and trivia

Sail Vineyard Haven Harbor with brunch bites, mimosas, and live jazz

Explore Sengekontacket Pond from State Beach with stable kayaks and a quick on-water intro

Learn stand-up paddleboarding with a guided, beginner-friendly tour

Build paddling skills at any level with a private lesson

Paddle open-ocean routes to remote spots with guides on Martha’s Vineyard

Paddle at sunrise with breakfast and coffee included

Start your day with a beginner-friendly paddle board fitness class

Tour an oyster farm by boat and enjoy freshly shucked oysters

Paddle a clear-bottom kayak at night with glow lights on State Beach

Enjoy a carefree day on the beach while we handle all setup, gear, and cleanup

Build kayak skills with guided games and exploration for kids

Savor sunset views around Cape Cod and Martha's Vineyard on an exclusive evening cruise for your group

Paddle Popponesset Bay at sunset and into the full moonlight

See Cape Cod Bay's low-tide sands by fat bike

Paddle Cape Cod’s quiet marshes with guidance for every experience level

Paddle Cape Cod waters with gear delivered to your launch area