things to do in Oak Bluffs, MA

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

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

Glide across Nantucket Harbor on your choice of kayak or paddleboard

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

Meet ghostly hosts with Revolutionary War stories to tell

See Cape Cod Bay's low-tide sands by fat bike

Savor sunset views around Cape Cod and Martha's Vineyard on an exclusive evening cruise for your group

Rent a kayak or paddleboard and explore State Beach from the water

Learn to ride a LIFT eFoil with a 2-hour lesson for up to 3 or 6 riders

Taste local traditions and uncover the stories behind New Bedford's cobblestone streets

Reserve a performance road bike in advance for your Edgartown ride

Set your own course across Popponesset Bay

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

Trace Nantucket’s Quaker and maritime past on a private narrated ride

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

Cruise Oak Bluffs waters on a Yamaha WaveRunner with professional instruction

Set sail on a private classic sloop tailored to your group

Paddle Cape Cod’s quiet marshes with guidance for every experience level

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

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

Ride together for a captain-guided tubing adventure on the water

Catch the bay breeze past New Bedford's working waterfront

Cruise the island on a pedal-assist Townie e-bike with 3 speed settings

Pick up a kayak or paddleboard at Lawrence Pond and explore at your own pace