things to do in Oak Bluffs, MA

Cruise comfortably with a bike built for relaxed riding

Explore Martha’s Vineyard waters aboard a private 38-foot Fountain charter

Bring your favorite food and drinks for an evening on Nantucket Harbor

Paddle into a Cape Cod sunset with an ACA-certified guide

A relaxed guided paddle with a midway ice cream boat stop

Paddle through a clue-filled pirate quest with a water cannon showdown

Paddle from State Beach with a quick lesson and gear included

Rent a kayak or paddle board and explore Oak Bluffs from the water

Build kiteboarding skills with tailored instruction and boat support

A tailored on-water session for families and groups

Ride Martha’s Vineyard trails on a Trek hardtail mountain bike

Build sailing skills with private coaching tailored to your goals

Paddle Scorton Creek with an ACA-certified guide, with routes picked for the tides

Rent a carbon fiber hybrid bike for smooth rides and fitness-focused comfort

See Nantucket's whaling-era landmarks from the water before the day gets busy

Ride from Oak Bluffs to Edgartown with island views and a beach stop

Learn paddleboarding basics with an ACA certified guide

Gather your group for music, drinks, and water views around Nantucket

Schedule island-wide kayak delivery and pick up

Build kayaking and paddleboard skills on a 4-day kids series at Sengekontacket Pond

Help your toddler build confidence on the water with an instructor-led sailing introduction

Ride a banana boat along State Beach with daily half-hour departures

Pick up at Scorton Creek and paddle Cape Cod at your own pace

Build paddling skills at any level with a private lesson