Come Sail away

Explore Cape Cod's Stage Harbor and Nantucket Sound aboard our J/97 sailboat or our 22' Angler powerboat

Call Us & Book Your Experience: (774)994-0637

Please Note: Scheduling our sailboat charters is heavily dependent on the tide in Stage Harbor. Due to the weather patterns and currents in the area, the channel to the Sound has become shallower and our sailboat can only make it out of the harbor at specific times.

Why Choose Us?

Over 20 years of boating experience

United States Coast Guard Licensed Captain

Flexible availability, including nights and weekends

Our Services

Half Day Sail

Full Day Sail

Sunset Sail

Sunset Harbor Tour

Day-time Harbor Tour

Additional Charter Hours

* Charter pricing is available on the Services page.

"If you are in the Chatham area, do yourself a favor and charter a trip with Son of a Sailor. A sailing cruise with Drew and Katie is a great way to see the Cape from a unique perspective. We thoroughly enjoyed our trip and plan to book another this season. Highly recommended!"

charlie & Kelley

hughes

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