Best 155 things to do in Oak Bluffs, MA

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

Refine your sailing technique and build confidence on the water

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

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

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

Learn to fly above the water by eFoil, kite, wing, or boat

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

Get on the water with gear provided for a classic skiing session

Make waves together with coached wakeboarding, eFoiling, and tubing

Build wing-foiling skills with tailored instruction and boat support

Take in Nantucket Harbor views as the day turns toward sunset

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

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

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

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