things to do in Orleans, MA

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

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

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

Charter a private sail in Provincetown for up to 34 guests

Sail Boston during Sail Boston 2026 on the restored Schooner Hindu

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

Set out on a self-guided paddle through Popponesset Bay

Paddle Scorton Creek and create your own blown-glass piece

Delivered gear for exploring Cape Cod at your pace

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

Take the helm of a forgiving catamaran for easy bay sailing

Taste Truro Vineyards wines and spirits aboard a historic schooner

Beginner stand-up paddleboard tour with ACA-certified guidance

Private classic schooner sail with lighthouse and cove views

Paddle Popponesset Bay at sunset and into the full moonlight

Build foundational paddling skills with an ACA-certified guide

Set your own pace with delivered gear for exploring Cape Cod by land or water

Get Cape Cod gear delivered for two days of self-guided exploring