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Couples Sailing School
Island Dreamer
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Couples teaching  Couples

Cruising classes for couples are an innovative way to learn about sailing and are designed to help you discover the joy of cruising together.  While on a learn-to-sail vacation, couples build confidence in each other with personalized instruction in an easygoing, positive environment that makes sailing together enjoyable.


Class Pricing


One-on-one instruction on a private charter guided by two licensed captains in all our classes. Our supportive approach allows each of you to build your skills and confidence at your own pace and to share in the decision making process, making sailing comfortable for everyone.You will be living and traveling aboard a cruising sailboat anchoring at a new place each night.    


American Sailing Association certifications are optional on all our cruises through Island Dreamer Sailing School, a certified ASA affiliate.  Our captains, most of whom live aboard the boats used in our program, are certified ASA instructors.  For boaters who would like to travel further afield than our home base in the Florida Keys, we offer trips in the Caribbean and Greece. If you want more advanced training, we offer night sailing, celestial navigation and offshore passage making.  And when you are ready to buy your own boat, we can give unbiased help; from selection, training aboard and delivery assistance. Let us help you develop a cruising strategy that is right for you.

Who Are We?

•Gain the skills you need to sail together in harmony.


•Personalized instruction provided by two captains.


•Travel and learn on a live-aboard tropical vacation.


•ASA Basic sailing through offshore passage making.


•Catamaran  and Bareboat Cruising Certifications


•Private and personalized training on your sail boat or ours.


Captains Margie and Harold Partnered with Captains Ann and Bob so we could share with you how wonderful sailing together can be.  We have have invited a few select captain couple instructors to join us in providing easygoing live aboard sailing classes.

Island Dreamer Sailing School

Couples Sailing School