Island Dreamer Sailing School

Specialties

At Island Dreamer Sailing we offer liveaboard and daytime sailing classes. We are accredited by the American Sailing Association and offer American Sailing Association Certifications from Basic Keelboat through Offshore Passagemaking including Bareboat Cruising and the new Docking Endorsement. Sailboat lessons can be geared specifically for women and couples, making sailing a relaxing and enjoyable experience. Learn how to operate a keelboat from USCG licensed captains and ASA instructors with many years of cruising knowledge. All of our classes are private charters so you will get lots of helm time and personalized instruction.

Discover how you can be safe and comfortable in all types of conditions.

All-​inclusive vacations for families, couples and friends encompass sailing, snorkeling and fishing while living aboard and exploring the Keys. Our liveaboard charters anchor in a new place each night as we sail the Florida Keys.

History

Established in 2007.

In 2007 Captains Margie and Harold Ochstein started Island Dreamer Sailing School with the Idea of helping other couples fulfill their sailing dreams. They now have sailboats both in the Keys and the Caribbean teaching couples about cruising and living aboard sailboats.

They have been married for 36 years and have spent the last 30 years exploring the Florida Keys in canoes, powerboats and sailboats. Both have USCG Master’s licenses with sail endorsements and are scuba divers. Harold is an American Sailing Association certified sailing instructor and a certified rescue diver.

Our home base has been in Miami. Harold and Margie have worked together as Captain and Crew on the 83′ schooner «The Heritage of Miami II,» along with each running their own 41′ sailboats.

Besides their sailing school classes they take charters to the Greek Isles every September and run their boats in the Boy Scouts of America’s High Adventure Base in Islamorada, Fl Keys.

Meet the Business Owner

Harold O.

Business Owner

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 and down the East Coast of the USA from New York to Florida, crossing to the Bahamas and spending more time in the Keys, they purchased a 37′ Irwin. Since then, the cruising continued throughout the Bahamas, the Southeast USA and the Keys; and eventually, the Irwin was replaced with a 41′ Morgan Out Island.

During the last seven years, home base has been in Miami in the winter and the Florida Keys in the summer. Harold and Margie each captain there own 41′ Sailboat in the summer with the Boy Scout Eco-​Adventure program and team up to teach couples in the winter.