Best 166 things to do in Mashpee, MA

Pick up a bike in Oak Bluffs and ride the island your way

Get a 7-day bike rental delivered to your address in Oak Bluffs

Pick up a 7-day bike rental in Oak Bluffs

Discover Martha’s Vineyard’s iconic cliffs and villages on a flexible private tour.

Raise the sails or take the wheel on Martha's Vineyard waters

Reserve pedal or electric bikes with island-wide delivery

Pick up pedal or electric bikes for 1–6 days of island riding

Set sail on a private classic sloop tailored to your group

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

Sail past JAWS filming locations with movie trivia and shark-themed treats

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