Best 170 things to do in Oak Bluffs, MA

Explore Cape Cod waters with paddle gear delivered to your launch spot

End the day with a guided paddle as Cape Cod’s evening sky changes

Find your balance with a guided yoga flow on calm Cape Cod waters

A relaxed guided paddle with a midway ice cream boat stop

Paddle through a clue-filled pirate quest with a water cannon showdown

Hunt for treasure with a pirate crew at sea

Paddle Scorton Creek and create your own blown-glass piece

Take the helm of a Rhodes 19 sailboat

Glide across Nantucket Harbor on your choice of kayak or paddleboard

Build sailing skills with private coaching tailored to your goals

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

Help your toddler build confidence on the water with an instructor-led sailing introduction

Build sailing confidence with instruction tailored to your experience

Refine your sailing technique and build confidence on the water

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

Take in Nantucket Harbor views as the day turns toward sunset

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

Build kiteboarding skills with tailored instruction and boat support

A tailored on-water session for families and groups

Fish Cape Cod Bay on a private 4-hour charter for up to 6 people

Fish Cape Cod Bay on a private 3-hour charter for up to 6