Best 52 things to do in Provincetown, MA

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

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

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

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

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

See Plymouth Harbor highlights with live narration from an expert crew

2-hour Plymouth Harbor party cruise with DJ, onboard bar, and landmark views

Cruise Plymouth Bay at sunset with a classic clambake dinner on board

Nighttime harbor cruise with ghost stories and Plymouth history

Sail into the Plymouth sunset with live music, appetizers, and unlimited drinks

Join a pirate crew mission with treasure maps and water cannons

Build your own ice cream sundae on a 75-minute Plymouth harbor cruise

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

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

Private 1-hour Shark Center tour with interactive exhibits and time to self-explore

Spot white sharks by boat with a spotter pilot and onboard naturalist

7–8 hour white shark and whale expedition with onboard experts

Join a spotter-piloted open-boat white shark tour that supports research