Best 170 things to do in Oak Bluffs, MA

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

Hear Nantucket’s Quaker and maritime stories at landmark stops

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

Cruise, fish, and relax aboard a spacious 200hp Whaler

Explore Nantucket waters on a spacious 275-hp boat for up to 9 people

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

Bring approved breakables and smash them in your own private rage room

Break stress your way with music, safety gear, and a room of breakables

Release stress with breakables, your own music, and a private rage room

Smash a full set of breakables while playing your own music

Smash glass, play your music, and let off steam in a private rage room

Smash office-themed breakables and make your own soundtrack

Get messy with neon paint, music, and a canvas to take home

Seasonal tastings and local tales on a relaxed walk through Chatham

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

Paddle Sengekontacket Pond with a private guide tailored to your group

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

Cruise Oak Bluffs waters on a Yamaha WaveRunner with professional instruction

Explore Martha’s Vineyard waters aboard a private 38-foot Fountain charter

Ski, wakeboard, kneeboard, or tube with professional instruction

Ride from Oak Bluffs to Edgartown with island views and a beach stop

Ride a banana boat along State Beach with daily half-hour departures

Get out on the water aboard a 17-foot Boston Whaler