Best 124 things to do in Brewster, MA

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

Pick up at Popponesset Bay and paddle at your own pace—off the water by 5:30 PM

Rent kayaks, paddleboards, and bikes with delivery and pickup across Cape Cod

Explore Cape Cod trails and waterways with a local outdoor community

Stand-up paddleboard tour up Scorton Creek with an ACA Certified guide

Beginner stand-up paddleboard tour with ACA-certified guidance

Explore Falmouth waters at your own pace

Ride Cape Cod’s coastal bike path with ocean views and local history

Explore Cape Cod waters at your own pace

Build foundational paddling skills with an ACA-certified guide

Pedal across Cape Cod Bay’s exposed sands at low tide

Paddle Cape Cod’s quiet marshes with guidance for every experience level

Get delivered paddleboard or kayak gear and explore Cape Cod waterways your way

Explore Cape Cod waterways with delivered paddleboard or kayak rentals

Paddle into a Cape Cod sunset with time to swim or stroll the beach

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

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

Explore Shark Alley by private motorboat with expert guidance and aerial spotting

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