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Catboat Charters is Martha’s Vineyard’s most unique and intimate  sailing charter. We offer private sailing charters for up to six guests aboard an antique 1927 wooden catboat yacht. Let your worries melt away as Captain Kurt and his first mate whisk you away from bustling downtown Edgartown for an unforgettable scenic adventure under sail.

At Catboat Charters, our guests’ comfort, safety, and satisfaction are our top priority. All of our charters include bottled water and sparkling water from our cooler. Guests are also welcome to bring any snacks and refreshments they desire. Our cockpit is very spacious and comfortable, with new seat cushions and pillows. There is more than enough room for guests to spread out or snuggle up for a memorable private sail.

A private sail aboard a historic catboat like Tigress is the epitome of a Martha’s Vineyard experience, because catboats have sailed these waters for hundreds of years. They were originally the fishing boats and passenger ferries of this area, but have transformed into the ideal pleasure craft over the past century. Catboats have very shallow drafts because they were designed to sail the skinny waters of the Cape and Islands. As a result, we are able to sail closer to shore than most other sailboats, achieving the perfect balance of scenery and serenity.

Tigress‘s American Flag sail is a tribute to the catboat Cleopatra that sailed these waters during the Civil War as a symbol of reunification between the North and South. Her current sail was stitched in February 2019 by Captain Kurt and Julia Doyle-Kingsbury of Squeteague Sailmakers. While her workboat roots are evident, Tigress was built as a recreational cruising yacht with very comfortable accommodations above and below decks, including a private enclosed head. Tigress has been meticulously restored and maintained and is a living reminder of old world luxury from the 1920s.

The following rates are for two hour long private sails and include all taxes and fees.

A 50% deposit is required to reserve your private sail. All major credit cards are accepted.

CANCELLATION POLICY: In case of bad weather: If it rains, or is too windy to sail (25 knots or more), we will promptly issue a 100% refund of your deposit if we are unable to rechedule for a mutually agreeable time. If you cancel your private sail with at least two week’s notice for ANY REASON, we will issue a full refund of your deposit.

To book, please call Capt. Kurt at 508 524 6903. We are currently taking reservations for our 2020 season. Advance reservations are highly recommended as availability is limited. We look forward to speaking with you and answering any questions you may have.

Spring Season Rates (May 24th through June 27th) for a private two hour sail for up to six guests.

Afternoon Sail: $450

Sunset Sail: $500

Summer Season Rates (June 28th through September 7th)

Early Afternoon Sail: $500

Late Afternoon Sail: $550

Sunset Sail: $600

Fall Season Rates (September 8th through October 8th)

Afternoon Sail: $450

Sunset Sail: $500

DISCOUNTS: Can not be combined. Limit one discount per booking.

Veterans and active duty, first responders, Martha’s Vineyard residents and seniors enjoy 10% off your sail in 2020. Please mention this to Captain Kurt when you book your sail by calling 508 524 6903. we can’t wait to sail with you!