Best 152 things to do in Chatham, MA

Build sailing confidence with instruction tailored to your experience

Refine your sailing technique and build confidence on the water

Private 3-hour beach cruise for up to six, with snacks and soft drinks included

Set your own course for a private outing on the water

Sail Cape Cod Bay on a family-friendly cruise where you can help raise sails and bring a picnic aboard

Watch Provincetown’s shoreline glow from a classic Victorian yacht

Sail Cape Cod Bay on the historic Schooner Hindu

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Sail Boston during Sail Boston 2026 on the restored Schooner Hindu

Taste Truro Vineyards wines and spirits aboard a historic schooner

Cruise Provincetown Bay at sunset with snacks and soft drinks

Take the helm of a Rhodes 19 sailboat

Glide across Nantucket Harbor on your choice of kayak or paddleboard

Enjoy a private evening cruise past Provincetown’s historic lighthouses

Private whale watch with a sunset cruise in Provincetown Harbor

See Cape Cod Bay's low-tide sands by fat bike

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

Paddle Cape Cod waters with gear delivered to your launch area

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

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