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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, sparkling water, and an assortment of cheese and crackers. Guests are also welcome to bring any snacks and refreshments they desire. There is no need to worry about how to keep your drinks cold, because we always have a cooler brimming with ice onboard. Our cockpit is very spacious and comfortable, with seat cushions, throw pillows, and blankets. 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 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 (restroom). 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 2019 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: $400

Sunset Sail: $450

Summer Season Rates (June 28th through September 2nd)

Early Afternoon Sail: $400

Late Afternoon Sail: $450

Sunset Sail: $550

Fall Season Rates (September 3rd through October 8th)

Afternoon Sail: $400

Sunset Sail: $450

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

U.S. Military Veteran and Active Duty: 15% (Military ID Required)

Police, Fire Fighters, and EMT’s: 10% (ID required)

Martha’s Vineyard Resident: 10% (ID with Vineyard address required)

Seniors: 10% (at least one guest is 65 years or older)