Best 57 things to do in Oak Bluffs, MA

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

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

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

Ride Martha’s Vineyard trails on a Trek hardtail mountain bike

Rent a carbon fiber hybrid bike for smooth rides and fitness-focused comfort

Customize a private 4-hour Martha’s Vineyard island tour with flexible stops

Tour Martha’s Vineyard’s 6 towns in 3 hours, with a stop at Aquinnah cliffs

Tour all 6 Martha’s Vineyard towns in 3 hours, with time for photos and a Menemsha stop

Join the crew for a treasure hunt with sea chanteys, stories, and cannon action

Book a spacious, stable 30' custom boat for an inshore fishing trip for up to 6 anglers

Fish Nantucket inshore waters on a spacious, stable 30' custom boat built for up to six anglers

Fish inshore on a 23' center console skiff built for comfortable rod room and a smooth ride

Taste wine, beer, and spirits while learning how Nantucket’s top producers craft each pour

Enjoy a two-hour self-guided sail aboard a stable Rhodes 19 from Jetties Sailing Center

Learn to sail with a private instructor at Jetties Beach

Glide across Nantucket Harbor on your choice of kayak or paddleboard

Build sailing skills with a private youth lesson for up to 3 sailors

Introduce your toddler to sailing with a 1-hour instructor-led lesson