Best 183
things to do in Chatham, MA
Showing 169-183 of 183 results
Private Whale Watch in Harwich
Share a private motorboat charter as you watch for whales off Cape Cod
4.8 • 140 reviews
14' Catamaran Rental on Pleasant Bay
Take the helm of a forgiving catamaran for easy bay sailing
4.8 • 140 reviews
Cape Cod 24-Hour Bike, Kayak & Paddleboard Rental
Delivered gear for exploring Cape Cod at your pace
5.0 • 226 reviews
Year-Round Guided Outdoor Adventures in Cape Cod
Connect with fellow explorers on guided Cape Cod outings
5.0 • 226 reviews
Sail Boston Harbor on the Historic Schooner Hindu
Sail Boston during Sail Boston 2026 on the restored Schooner Hindu
Sunset Wine Tasting Cruise in Provincetown
Taste Truro Vineyards wines and spirits aboard a historic schooner
Fish Cape Cod Bay on a 6-Hour Charter
Join a 6-hour Cape Cod Bay fishing charter with a licensed captain
90-Minute Private Schooner Charter in Provincetown
Private classic schooner sail with lighthouse and cove views
Paddleboard Scorton Creek Guided Tour
Stand-up paddleboard tour up Scorton Creek with an ACA Certified guide
5.0 • 226 reviews
2-Hour Stand-Up Paddleboard Tour on Popponesset River
Beginner stand-up paddleboard tour with ACA-certified guidance
5.0 • 226 reviews
Full Moon Kayak Tour On Popponesset Bay
Paddle Popponesset Bay at sunset and into the full moonlight
5.0 • 226 reviews
Beginner Kayak Lesson in Sandwich
Build foundational paddling skills with an ACA-certified guide
5.0 • 226 reviews
6-Day Cape Cod Bike, Kayak & Paddleboard Rentals
Set your own pace with delivered gear for exploring Cape Cod by land or water
5.0 • 226 reviews
2-Day Bike, Kayak & Paddleboard Rentals in Cape Cod
Get Cape Cod gear delivered for two days of self-guided exploring
5.0 • 226 reviews