About Us


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Island Dreamer Sailing School’s Website

Captain Margie and Captain Harold have been married for 35 years and have spent the last 30 years exploring the Florida Keys in canoes, powerboats and sailboats. We started Island Dreamer Sailing School in 2008 to help couples learn about sailing together. We both have USCG  Master’s licenses with sail endorsements and are scuba divers.  Harold is an ASA certified sailing instructor and a certified rescue diver.

In 1995, Margie and Harold purchased their first sailboat, a 25’ Venture, which was replaced several years later with a 27’ Catalina.  After 6 years of weekend sailing in Biscayne Bay and the Florida Keys, with some month-long trips to the Bahamas, the time came to move aboard and cruise.

After cruising up the East Coast of the USA from New York to Florida, crossing to the Bahamas and spending more time in the Keys, we purchased a 37’ Irwin.  Since then, we have continued cruising in the Bahamas, the Southeast USA and the Keys.

With the idea of opening our boat up to charters, we sold the Irwin and purchased a 41’ Morgan, chartering it with the Boy Scouts of America High Adventure Sea Base in the Keys.  In addition, we captained the 83’ Schooner Heritage of Miami in the BSA program and also ran day trips on the Heritage in Biscayne Bay from downtown Miami. We have run the Boy Scouts Eco Adventure program in the summers since 2009. The rest of the year we help couples and families learn the joy of sailing together with crewed classes and charters on out sailboats. Visit our website here.

Florida Keys Sailboat Lessons from Experienced Captain | Florida Keys Sailboat Lessons

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