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Island Dreamer Sailing
Clear warm waters sailing with dolphins with couples on board a sailboat in Biscayne Bay
Reluctant Partner?

Our “no yelling” style will ease any concerns that you and your partner may have about sailing or about the cruising lifestyle. Let us show you how enjoyable it can be.

We Make Sailing Fun
women taking sailing lessons and  asa certifications classes for couples
teaching couples to work to gether with no yelling

Learn about sailing and living aboard in a relaxed environment with Captain Margie and Captain Harold Ochstein in Miami and the Florida Keys. The sailing is easygoing in the calm, protected water of this versatile marine environment off the southern coast of Florida. Anchor in a new spot each night as we explore the Keys. Bounded by the Gulf Stream and coral reefs of the Atlantic Ocean and the shallow flats and back country of Florida Bay, this warm, sunny string of tropical islands is the perfect retreat from stress.

Couples will enjoy working with Captains Margie and Harold building confidence and learning about sailing. Together with your partner, you will learn how to feel safe and comfortable and in control of your boat. We believe that once you learn the skills of boat handling, however, you have only learned part of the equation. The other part is working together as a team. Captain Margie and Captain Harold, who are both Coast Guard licensed captains, will work with you both individually and as a couple in a gentle and calm environment.

As a couple learn the skills you need for cruising while living aboard with us on our 41’ Morgan Out Island sailboat. Beginning sailors can practice and learn basic sailing skills on our 20’ keelboat. Learn about sailing, anchoring, docking and boat systems while exploring the protected waters of Biscayne Bay and the Florida Keys.

We will help you set goals so that you learn at your own pace and have a great time doing it. You may want to take ASA Certification classes, including Bareboat Certification, or you simply may want to practice all facets of the cruising and sailing life. All skill levels will benefit from the individualized lessons received from Captains Margie and Harold.

Life onboard is not all study and boat handling, however. We visit local island restaurants to enjoy fresh seafood, tropical drinks and live music. And of course, snorkeling, fishing and socializing with other cruisers is all part of the plan. Let us show you how enjoyable the cruising life can be.

Your learn to sail vacation is a private charter. We anchor at a new spot each night with time to get ashore at a state park or a “tiki Bar” for some live music. You will have lots of time learning how to operate  and navigate a sailboat so you can cruise in on your own or  do bareboat charters.

Learn More

Info about the captains, the boats and the Florida Keys.

ASA Classes

Certifications from the American Sailing Association are known worldwide.

Couples Sailing

Learn in a friendly setting where “no yelling” is allowed.