Best 54 things to do in Chatham, MA

Cruise Provincetown Bay at sunset with snacks and soft drinks

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

Book a private whale watch to Stellwagen Bank in Provincetown

Enjoy a private evening cruise past Provincetown’s historic lighthouses

Private whale watch with a sunset cruise in Provincetown Harbor

Choose your beach and use the boat as your home base for swimming and relaxing

Cruise for seals, fish, and lobster traps with the kids

Cruise past three historic lighthouses and visit a local seal colony

Sail Provincetown in the afternoon on a 2-hour cruise

Enjoy a relaxing two-hour cruise as daylight fades over the water

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

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

Spot white sharks by boat with a spotter pilot and onboard naturalist

7–8 hour white shark and whale expedition with onboard experts

Join a spotter-piloted open-boat white shark tour that supports research

Cruise Cape Cod waters with a naturalist team on an open-boat white shark charter

Private 2.5–3 hour white shark charter with a spotter pilot and AWSC naturalist

Charter a private boat for Pleasant Bay’s Fourth of July fireworks