things to do in Orleans, MA

Share a Chatham Harbor motorboat cruise and look for seals

Set your own course across Popponesset Bay

See Cape Cod Bay's low-tide sands by fat bike

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

Seasonal tastings and local tales on a relaxed walk through Chatham

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

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

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

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

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

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

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

Paddle Cape Cod waters with gear delivered to your launch area

Cruise Wellfleet Harbor at sunset on a private charter for up to 6

Private whale watch with a sunset cruise in Provincetown Harbor

Learn sailing fundamentals with private on-water instruction

Sail Cape Cod Bay on a family-friendly cruise where you can help raise sails and bring a picnic aboard