Water Activities in Orleans, MA

Watch Cape Cod's vibrant sunset while enjoying onboard cocktails and treats

Hunt for treasure with a pirate crew at sea

Search for whales on Stellwagen Bank aboard a boat reserved exclusively for your group.

Sip, Savor & Cruise: Narrated Harbor Views with Cocktails and Ice Cream Treats Onboard

Sail Cape Cod Bay on the historic Schooner Hindu

Share a Chatham Harbor motorboat cruise and look for seals

Set your own course across Popponesset Bay

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

Private 3-hour morning bay cruise for up to 6

Fish for sharks off Cape Cod on an 8-hour private charter

Book a private whale watch to Stellwagen Bank in Provincetown

Share a whale watch trip from Provincetown and split the boat with other travelers

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

Private 3-hour beach cruise for up to six, with snacks and soft drinks included

Sail Provincetown at sunset on the historic Schooner Hindu

Pick up a kayak or paddleboard at Lawrence Pond and explore at your own pace

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Paddle Cape Cod waters with gear delivered to your launch area

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

Paddle Popponesset and Ockway bays at sunset with an ACA-certified guide

Explore Cape Cod waters with paddle gear delivered to your launch spot

Sail Wellfleet Harbor on a private 3-hour charter, with tide-based stops for swimming or beach time

Fish Cape Cod waters on a private 8-hour charter for up to 6 people

Enjoy a private evening cruise past Provincetown’s historic lighthouses