Best 59 things to do in Oak Bluffs, MA

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

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

See Nantucket landmarks on a 90-minute narrated bus or van tour

Explore Nantucket’s historic landmarks on a private 90-minute narrated ride

Rent a 21 ft Boston Whaler for cruising or fishing in Nantucket

Watch the sun set over Menemsha Beach aboard a comfy shuttle with dinner options and local commentary

Discover all six Martha's Vineyard towns in a small-group guided bus tour.

Soar up to 600 feet over the sea on a parasailing flight

Rent a Yamaha WaveRunner and cruise Oak Bluffs for 1 hour

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

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

Enjoy a carefree day on the beach while we handle all setup, gear, and cleanup

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

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

Build paddling skills at any level with a private lesson

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