Best 155 things to do in Oak Bluffs, MA

Set sail on a private classic sloop tailored to your group

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

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

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

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

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

Rent a kayak or paddleboard and explore State Beach from the water

Paddle from State Beach with a quick lesson and gear included

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

Schedule island-wide kayak delivery and pick up

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

Build paddling skills at any level with a private lesson

Rent a paddleboard for 24 hours at State Beach in Oak Bluffs

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

Paddle at sunrise with breakfast and coffee included

Build kayak skills with guided games and exploration for kids

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

Rent a kayak or paddle board for 1–3 months with free delivery

Paddle Sengekontacket Pond with a private guide tailored to your group

Reserve a performance road bike in advance for your Edgartown ride

Cruise the island on a pedal-assist Townie e-bike with 3 speed settings

Cruise to town or the beach on a comfy 7-speed Townie

Cruise comfortably on a hybrid commuter bike with helmet and lock included

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