things to do in Chatham, MA

Enjoy a private evening cruise past Provincetown’s historic lighthouses

Take in Provincetown's dunes and sunset from a private open-air Bronco

Rent a 2-person kayak for 24 hours to 1 month

Pick up a kayak or paddleboard at Lawrence Pond and explore at your own pace

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

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Cruise Chatham Harbor privately and watch for seals with your group

Seasonal tastings and local tales on a relaxed walk through Chatham

See Nantucket's harbor from the water with ice cream for everyone

Paddle Cape Cod waters with gear delivered to your launch area

Cruise Wellfleet Harbor at sunset on a private charter for up to 6

Fish Cape Cod waters on an 8-hour private striper charter for up to 6

Private whale watch with a sunset cruise in Provincetown Harbor

Explore the Outer Cape's dunes, then unwind by the water at sunset

Rent a canoe for 24 hours to 1 month and get on the water

Ride the Cape Cod Canal with an 8-hour bike rental

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

Explore rare sandplain grasslands and the quieter shores of Hummock Pond

Share a private motorboat cruise as evening settles over the harbor

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

A family-friendly private harbor outing with ice cream for everyone

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

Uncover exhibit details you might miss on your own

Fish for tuna on a 10-hour private Cape Cod charter (up to 4 people)