Best 43 things to do in Brewster, MA

Taste Truro Vineyards pours on a 2-hour schooner sail in Provincetown

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

Search for whales on Stellwagen Bank aboard a boat reserved exclusively for your group.

Share a whale watch trip from Provincetown and split the boat with other travelers

Book a private whale watch to Stellwagen Bank in Provincetown

Enjoy a private evening cruise past Provincetown’s historic lighthouses

Private whale watch with a sunset cruise in Provincetown Harbor

Choose your beach and use the boat as your home base for swimming and relaxing

Cruise for seals, fish, and lobster traps with the kids

Cruise past three historic lighthouses and visit a local seal colony

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

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

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

Private 2.5–3 hour white shark charter with a spotter pilot and AWSC naturalist

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

Sail a restored 1925 schooner at sunset with drinks and charcuterie

Charter a sailboat in Key West for up to 42 guests

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Sail Boston during Sail Boston 2026 on the restored Schooner Hindu