things to do in Chatham, MA

Gather your group for music, drinks, and water views around Nantucket

Share a sunset motorboat ride through the harbor

Cruise Nantucket waters while uncovering the island's whaling-era landmarks

Paddle Lawrence Pond your way with a 1-hour kayak or paddleboard rental

Refine your sailing technique and build confidence on the water

Take to the water in a Boston Whaler Montauk

Fish Cape Cod Bay on a private 4-hour charter for up to 6 people

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

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

Paddle Popponesset Bay at your own pace with included gear

Ride the Cape Cod Canal on your own schedule with a 4-hour bike rental

Cast a line on a private inshore trip with a captain and gear included

Spend a private day exploring Nantucket by boat

Set out on a private captain-led motorboat outing with your group

Make Nantucket Harbor your private setting for an evening cruise timed for sunset

Private family kayak lesson with ACA (American Canoe Association) certified guides

Cruise Provincetown Bay at sunset with snacks and soft drinks

Watch Provincetown’s shoreline glow from a classic Victorian yacht

Fish Cape Cod Bay on a private 3-hour charter for up to 6

Try fishing in Cape Cod Bay on a 2-hour kids-friendly private charter

Charter a private sail in Provincetown for up to 34 guests

Set out on a self-guided paddle through Popponesset Bay

Paddle Scorton Creek and create your own blown-glass piece

Set sail privately with your group on Pleasant Bay