things to do in Brewster, MA

Cruise Provincetown Bay at sunset with snacks and soft drinks

Watch Provincetown’s shoreline glow from a classic Victorian yacht

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

Set your own course for a private outing on the water

Charter a private sail in Provincetown for up to 34 guests

Cast a line on a private inshore trip with a captain and gear included

Spend a private day exploring Nantucket by boat

Ride the Cape Cod Canal on your own schedule with a 4-hour bike rental

Set out on a private captain-led motorboat outing with your group

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

Set out on a self-guided paddle through Popponesset Bay

Paddle Scorton Creek and create your own blown-glass piece

Set sail privately with your group on Pleasant Bay

Sail Boston during Sail Boston 2026 on the restored Schooner Hindu

Taste Truro Vineyards wines and spirits aboard a historic schooner

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

Private classic schooner sail with lighthouse and cove views

Share a private motorboat charter as you watch for whales off Cape Cod

Take the helm of a forgiving catamaran for easy bay sailing

Delivered gear for exploring Cape Cod at your pace

Connect with fellow explorers on guided Cape Cod outings

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

Beginner stand-up paddleboard tour with ACA-certified guidance