sail boat with main inn

Sailing Trips

Enjoy a sail on a beautiful day or a relaxing evening sail while the sun sets to the west. The sweeping vistas of Chatham’s coastline, historical landmarks like the Chatham Lighthouse and North Beach Island provide the perfect backdrop for your sail. Daily one-hour sailing trips are available at 11am, 1pm and 3pm. One-hour evening sails are daily at 5pm. 

Private Sails

A late-morning or late-afternoon sail is a wonderful way to enjoy sweeping vistas of Chatham's coastline. You will sail past the historic Chatham Lighthouse and North Beach Island, part of the Cape Cod National Seashore. These sailing trips are available for 1 or 2 hours. 

Sailing Instruction 

Available upon request, our instructors will provide guests with basic sailing instruction in a safe and fun environment. The goal is for each guest to develop skills while building knowledge and confidence. Learn basic boat handling, terminology, rigging and sail trim. Participants must be 7 years of age or older. 

Boating FAQs

Boating is available from May through October. Space is limited and many of these experiences sell out quickly, so make sure to reserve as far in advance as possible by calling 508.945.6871.

If you need to change or cancel your reservation, we do require notice 24 hours in advance. Please note all boating excursions are subject to change.

Are the tours family friendly?

Yes! Kids and adults alike are sure to have a great time on any of our boating excursions.

Can I book boating for my wedding party, bachelor/bachelorette party or other occasion?

Absolutely! These tours are a great way to make memories and bond with those close to you.

How far in advance should I reserve my boating?

We recommend reserving as far in advance as possible. Boating excursions fill up quickly and are limited to small private groups. We are now accepting reservations for the entire 2023 boating season. Call 508.945.6871 to book.

What kinds of wildlife will I see?

On any trip out on the water, you will see all kinds of animals in their natural habitat including grey and harbor seals who are often found basking on sandbars or frolicking in the water depending on the tide.

Our whale watching tour guests primarily spot humpback whales, but often see pilot whales, minke whales, whale sharks and giant mola mola as well.

Private white shark charters focus on viewing great white sharks, though you may experience other wildlife that Cape Cod has to offer, such as grey seals. 

What should I bring?

Prepare to bring several items with you to make your trip a successful one. We recommend bringing sunscreen, polarized sunglasses, a hat and a camera as well as an extra sweater or windbreaker as it's cooler on the water than on land.