Sail Vineyard Sound with lighthouse views and secluded swim options
Raise the sails or take the wheel on Martha's Vineyard waters
Raise the sails or take the wheel aboard a historic schooner
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
Explore JAWS movie history with shark-themed drinks and trivia
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
Rent a paddleboard for 24 hours at State Beach in Oak Bluffs
Paddle at sunrise with breakfast and coffee included
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
See Pleasant Bay, Chatham, and the Lower Cape from above
Aerial views of Chatham, Orleans and Cape Cod National Seashore