Best 53 things to do in Chatham, MA

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

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

Join the crew for a treasure hunt with sea chanteys, stories, and cannon action

Private 3-hour morning bay cruise for up to 6

Sail Wellfleet Harbor on a private 3-hour charter, with tide-based stops for swimming or beach time

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

Cruise Cape Cod’s outer beaches with a spotter pilot to look for great white sharks

Sail Provincetown Harbor and Cape Cod Bay on a private 6-hour charter

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

Sail Cape Cod Bay at sunset on a bring your own food and drinks cruise

Sail a restored 1925 schooner at sunset with drinks and charcuterie

Sail Cape Cod Bay on the historic Schooner Hindu

Charter a private sail in Provincetown for up to 34 guests

Charter a sailboat in Key West for up to 42 guests

Sail Provincetown at sunset 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 pours on a 2-hour schooner sail in Provincetown

Charter a private sail for up to 42 people from MacMillan Pier

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

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