Best 128 things to do in Brewster, MA

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

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

Join a 6-hour Cape Cod Bay fishing charter with a licensed captain

Charter a private boat for Pleasant Bay’s Fourth of July fireworks

Learn sailing fundamentals with private on-water instruction

Share a sunset motorboat ride through the harbor

Fish Cape Cod waters on a private 8-hour charter for up to 6 people

Sip, Savor & Cruise: Narrated Harbor Views with Cocktails and Ice Cream Treats Onboard

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

Hunt for treasure with a pirate crew at sea

Paddle Scorton Creek and create your own blown-glass piece

Cruise Provincetown Bay at sunset with snacks and soft drinks

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 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

Enjoy a private evening cruise past Provincetown’s historic lighthouses

Private whale watch with a sunset cruise in Provincetown Harbor

Cast, jig, and troll for striped bass and bluefish with crew support

Paddle Popponesset Bay at sunset and into the full moonlight