Island Dreamer Sailing School

I was looking for a sailing school to get my bareboat certification and came upon Island Dreamer. The hook was that the owners, Harold and Margie, were both ASA certified instructors as well as Captains, and specialized in teaching couples how to sail. My wife is a very skittish sailor and neither of us had spent the night on a boat before. Despite the mediocre weather conditions (rain for several hours the first two days), we could not have been happier with our 3-​day liveaboard course. Harold and Margie are experts, but they don’t make you feel stupid when you do stupid things! The boat was spacious and well-​maintained, and the meals were top notch. We couldn’t have had better companions to spend time with on a 41 foot boat. Best of all, I passed the written test at the end of the trip (my wife was allowed to audit the course so she would know what to do if we ever had an emergency when we charter by ourselves.) VERY HIGHLY RECOMMENDED

Very helpful and experienced staff. Very accomodating they show you the ropes and in no time you would feel confortable in sailing on your own, you also get a certificate and its very rewarding.

My girlfriend and I were visiting friends in Ft. Lauderdale and we decided to try to find an ASA-​certified school that could give us intro lessons on short notice. Luckily, we found Captain Harold and he bent over backwards to accommodate us and went on to give us great hands-​on lessons and a very detailed treatment of the ideas and rules that govern sailing. He was very kind and friendly throughout, and is very clearly an expert at what he does. I would strongly recommend him to anyone interested in learning how to sail or building on their existing knowledge. Thanks Capt. Harold!

We just returned from our four day couples sailing course and it was a wonderful (and unique) experience. Our goal was to achieve the ASA 101 and 103 certifications, and with Harold and Margie’s help we did it with time to spare. Both of the Ochsteins are skilled sailors, patient teachers, and have an encyclopedic knowledge of the local waters in the Keys and the Miami area. We got plenty of sailing time in the big 41′ Island Dreamer and also in their smaller (and less intimidating) 21′ boat, and still had time for a couple of fun evenings on shore. A bonus was the chance to see some of the local flora and fauna up close and personal — a big sea turtle, half a dozen porpoises, and and endless variety of birds native to the Keys. The calm, broad, shallow waters of the Keys turned out to be ideal for a couple of newbies with no sailing experience. What really makes this different from the average sailing school is that Harold and Margie aren’t just good instructors; the Island Dreamer is also their year-​round home (they live aboard), and we got to know these lovely and hospitable people very well by the end of our trip. If your taste in vacations runs to the intimate bed & breakfast experience, and you want to become a confident sailor, you’ll love the Island Dreamer experience. If you’re more the Marriott type, or think that twelve meals a day on a huge cruise ship is the perfect holiday, then you may want to think again; Island Dreamer (and sailing in general) may not be for you. It was perfect for us.