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Couples Sailing School
Island Dreamer
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We offer sailing classes around the world..

Florida Keys- Join Ann and Bob or Harold and Margie sailing on the cruising sailboat that is their home. Classes in the fall, spring and winter cruising the calm clear waters of Americas tropical paradise. Other boats and Captain Couples are also Available. As part of your cruising, experience more than just sailing - snorkel the third largest reef system in the world, kayak to the islands, and fish for your dinner. We have both catamaran and monohulls, take lessons or just relax and enjoy!

Bahamas- This November join Captain Louise exploring the Out Islands on her way to the Caribbean. You can make a Gulfstream passage or fly direct to the Bahamas.

Eastern Caribbean- Practice an offshore passage from the Turks and Caico’s and earn your ASA 108 certification or fly in to the Virgin’s Christmas week for some of the the best sailing in the world. Continue down the Island chain through the winter and spring.

Greek Islands-September is one of the nicest months to sail in Greece, the crowds are gone and the weather is wonderful. You can join Bob and Ann or Harold and Margie exploring one of the cradles of civilization, enjoy the friendly Greek culture and practice your Med moor. You will be stopping at a new Island each night with a 49’ sailboat as your home.

Just some of our Cruising Sailboats..

47’ Hylas-Blue Planet is equipped for offshore passage making in addition to being a comfortable cruiser set up for life aboard. Her sweet sheer and elongated more traditional lines are the unmistakable hallmark of legendary yacht designers, Sparkman and Stephens. Known for her crisp performance and elegant hand-finished teak interior, she is an absolute joy to handle, even with small crew. The integrity assured by her solid laminate hull and watertight bulkheads further speak to her mission as a reliable offshore performer or elegant coastal cruiser.

41’ Morgan Out Island- Island Dreamer and Morning Dance are proven shallow draft cruisers well suited to sailing in the Florida Keys. They have a center cockpit that is shaded by a large Bimini top and dodger. The interiors were recently refit, giving them a clean, spacious feel. Both boats have two staterooms, two heads with hot-water showers, a galley with refrigerator and freezer, and a large settee area in the main salon.  The settee can be converted into a bed for two when there are additional guests.  

40’ Kit Kat Catamaran-The Kit Kat 40 offers a rare combination in a cruising catamaran: good sailing performance and the ability to motor at 15+ knots! The Kit Kat is constructed light and stiff using aeronautical grade materials: nidacore in the deck and interior bulkheads, foam core topsides. The design is very seaworthy with high bridgedeck clearance, spacious decks, well ventilated interiors and a hard top bimini. All the comfort amenities you will need for extended cruising are aboard: generator, air conditioning, fridge, freezer, solar panels. This is the ideal craft for exploring the Florida Keys and see what life is like aboard a cat.

42’ Catalina Mark II sloop- The sleek and beautiful Selah (pronounced SAIL_AAH) is a spacious modern cruiser.  Her cockpit comfortably accommodates six guests plus the crew, and is covered with a bimini for protection from the elements.  Known for her stability, performance and smooth ride, she is a Coast Guard approved vessel, equipped with a modern gallery, a large salon, two private heads (bathrooms) and private cabins.

Most of the sailboats used in our programs are owned and lived aboard by our captain couples.

A Few of Our Sailboats