Best 119 things to do in Wellfleet, 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

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

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

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

Paddle Scorton Creek, then make your own glass piece in Sandwich

Paddle Popponesset Bay at sunset and into the full moonlight