things to do in Vineyard Haven, MA

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

Sail New Bedford Harbor and Buzzards Bay on a private charter

Fish Nantucket's shallow flats from a purpose-built private skiff

Explore JAWS movie history with shark-themed drinks and trivia

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

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

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

Explore Cape Cod waters with paddle gear delivered to your launch spot

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

Explore Sengekontacket Pond from State Beach with stable kayaks and a quick on-water intro

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

Make waves together with coached wakeboarding, eFoiling, and tubing

Build wing-foiling skills with tailored instruction and boat support

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

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

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

Sail close to the water on an interactive harbor charter

Bring your favorite drinks for a relaxed hour on Nantucket waters

Learn paddleboarding basics with an ACA certified guide

Paddle Lawrence Pond your way with a 1-hour kayak or paddleboard rental

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

A relaxed guided paddle with a midway ice cream boat stop

Paddle from State Beach with a quick lesson and gear included

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