things to do in Oak Bluffs, MA

Cover more of Martha's Vineyard with pedal-assist power

Rent a stand-up paddleboard for 24 hours to 1 month

A family-friendly private harbor outing with ice cream for everyone

Feel the road in a three-wheeled ride with open sky above

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

End the day with a guided paddle as Cape Cod’s evening sky changes

Explore Nantucket’s coastal habitats with local naturalist insight

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

Build wing-foiling skills with tailored instruction and boat support

Uncover exhibit details you might miss on your own

Cruise the island on a Specialized Como e-bike with pedal assist

Paddle Popponesset and Ockway bays at sunset with an ACA-certified guide

Cruise comfortably at your own pace on an easy-riding bike

Explore the water your way in a single recreational kayak

Bring your favorite drinks for a relaxed hour on Nantucket waters

Target tautog with fishing gear and green crab bait provided

Take the helm of a Rhodes 19 sailboat

Find your balance with a guided yoga flow on calm Cape Cod waters

Discover Nantucket's glacial past on an evening hike with harbor views

Reserve your kayak online and enjoy a full day on the water with included gear and basic instruction

Take in Nantucket Harbor views as the day turns toward sunset

Step into darkened galleries for pirate tales and haunting sea legends

Rent a premium dual sport bike for smooth riding on dirt roads and pavement

Paddle Cape Cod’s barrier beaches with an ACA-certified guide