Best 143 things to do in Chatham, MA

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

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

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

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

Explore Stellwagen Bank’s whale feeding grounds from a private boat

Leave land behind for sunset views over open water

Pedal across Cape Cod Bay’s exposed sands at low tide

Paddle Cape Cod’s quiet marshes with guidance for every experience level

Get delivered paddleboard or kayak gear and explore Cape Cod waterways your way

Explore Cape Cod waterways with delivered paddleboard or kayak rentals

Paddle into a Cape Cod sunset with time to swim or stroll the beach

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

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

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