things to do in Chatham, MA

Cast, jig, and troll for striped bass and bluefish with crew support

Take the helm of a Rhodes 19 sailboat

Rent a stand-up paddleboard for 24 hours to 1 month

Paddle Popponesset and Ockway bays at sunset with an ACA-certified guide

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

Explore a rare coastal habitat as daylight fades

Learn sailing fundamentals with private on-water instruction

Explore Stellwagen Bank’s whale feeding and nursing grounds by private boat

Bring your favorite drinks for a relaxed hour on Nantucket waters

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

Step into darkened galleries for pirate tales and haunting sea legends

Fish Cape Cod waters for bass and tuna on an 11-hour private charter

Private charter to fish for striped bass and bluefish and look for whales

Build sailing skills with private coaching tailored to your goals

Explore the water your way in a single recreational kayak

Paddle Cape Cod’s barrier beaches with an ACA-certified guide

Make waves together with coached wakeboarding, eFoiling, and tubing

Explore Nantucket’s coastal habitats with local naturalist insight

A private evening sail with room for your own refreshments

Leave land behind for sunset views over open water

Bring your favorite food and drinks for an evening on Nantucket Harbor

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

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

8-hour private haddock and pollock fishing charter for up to 6 people