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Dave Calvert

has been sailing for more than 40 years. Over this time he has logged over 60,000 miles of ocean sailing on boats he has owned. In addition to this, Dave has been a world-class racer, winning over 14 National Championships on catamarans and trimarans. Dave also was crew of Steve Fossett's 125 ft. mega-catamaran, PlayStation. During 2001 and 2002, as a driver onboard, he helped to set five world records including both Trans Atlantic records and the 24-hour speed record.

Dave has owned and operated Calvert Sails for over 37 years and continues to design and manufacturer world-class multihull and monohull sails. So, if you want to feel confidence in a skipper, Dave is your man. He is a current holder of a US Coast Guard captain's license with all Bahamas charter permits.

Also, if interested in learning how to sail or cruise, Dave is always willing to let you help trim the sails and take the helm. With years of sailing the Bahamas islands, Dave and his wife Trish know these islands intimately and will make your Bahamas cruise one to remember.

Tuna Tartar Salad

First Mate Trish 

Trish Calvert is the first mate and chef aboard Destiny III. She has been sailing with Dave for three decades. During this time, she has also logged many thousands of miles along the US east coast, Florida Keys, The Bahamas, Turks and Caicos Islands, Dominican Republic and Caribbean Islands to Trinidad. She was a sailing instructor for windsurfing and Hobie Cats, running one of the largest water sports companies in the Florida Keys. She has a love of cooking and is well-known for her culinary creations.

First Mate


Chef Steve has been working with us for a few years now. He is an accomplished Chef with 35 years experience in hotels, restaurants and research and development.

He comes up with some of the best culinary creations, wows our guests palate and just delights us with his fun presence and amazing dishes.

"The food from Chef Steve was incredible, our first dinner was the mahi-mahi which was everyone’s favorite."

"Chef Steve blew us away with his menu. The food is outstanding. We ate so well during our trip." 

See his resumé here.

Image by Jonathan Borba
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Alternate Captain and Chef

Kirk Jeannie

Captain Kirk Guay has been running sailing charters and boat deliveries for the past 4 years but has been boating since he was 12 years old in NH. Kirk’s first career was racing motorcycles where he won the New England superbike championship and further earned 13th nationally. After racing, he moved on the become a pilot and dive master between his career as a painting contractor.

Captain Jeanne Guay has also been chartering and delivering boats past 4 years but has been sailing since camp as a kid in RI. Jeanne has done a myriad of diverse work from massage therapist, sous chef, caterer, midwife, nurse, lactation consultant, canvas worker, dock master and restorer of vintage boats and campers. Be sure to ask about her roller derby days as well!


Together Kirk and Jeanne have sailed Lake Ontario, Winnipesaukee, northern East Coast, Bimini and all over the Gulf of Mexico. This work is truly a dream as they look forward to many more full bellies and adventures on the water!


They look forward to welcoming you aboard Destiny lll.

Captain Kirt and Chef Jeanne Guay.jpeg
Alternate Capt.
Captain Rob and Chef Anya photo_edit.jpg
Captain Rob and Chef Anya

Captain Rob hails from Melbourne Australia and grew up playing Rugby, Aussie rules football and body surfing.

He later moved to the Florida Keys and pursued his education to obtain his USCG 100 Ton Masters and also his certificates to become a Scuba instructor.

Rob loves the Exumas and cannot wait to show you the beauty that lies out there.

Anya grew up in In Southeast Asia (Bandung, Indonesia and Taipei, Taiwan) very close to the ocean. 

She loves Swimming, horseback riding, sailing, baseball, anything that involved sports. She then later obtained her Master’s degree from University of Trier and Louisiana State University, USCG Captain and Scuba Instructor certification. She has been cooking for others since she was 12, and has been working on sailing yachts for 35 years. Started as deckhand and soon went on to provisioning and cooking on board. Worked as a scuba instructor and had her own dive shop for 15 years, during which she also got her USCG Captain’s license. Rob and her went through hurricane Irma in the Keys and lead some of the ensuing relief, coordinating rescue efforts and feeding people. They have been living on their own 42 ft sailboat full time for the past 3 years.

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