Island Dreamer Sailing School

Join us in Miami and the Florida Keys for ASA learn to sail lessons, family and couples inclusive vacation charters or a very reasonably priced “captain only” charter. Sailing in the clear calm waters of this laid back island chain traveling along our warm, sunny tropical islands will make memories you will treasure for a lifetime.
ASA sailing classes while you live on board or easygoing daytime instruction. We are accredited by the American Sailing Association and offer all levels of ASA Certifications including Bareboat Cruising, Cruising Catamaran, Offshore Passagemaking and Docking Endorsements.
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.
One-on-one instruction on a private charter guided by two licensed captains. 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
Sailboat lessons can be geared specifically for women and famlies, Learn how to make sailing a relaxing and enjoyable experience. Lessons on how to operate and dock a keelboat from USCG licensed captains and ASA instructors with many years of cruising knowledge. Discover how you can be safe and comfortable in all types of conditions.
Come sailing with us for a day or a week, around Miami or a leisurely trip to the Keys. You set the agenda when you join us for a private charter. We anchor at a new place each night and all your meals are prepared for you. Relax, learn to sail the boat, go kayaking, explore ashore and swim or snorkel in the clear waters of Biscayne National and John Pennekamp Parks.
All-inclusive vacations are available for couples, families and friends. Learn about the Florida Keys on our multi-day eco tours, where we share our knowledge of local history and marine life. Day charters and sunset sails are available in downtown Miami. You may also want to join us on us on special sailing holidays to Greece, and The Bahamas.
Anchor at a new place each night while on all our liveaboard sailing classes. We will work with you to choose a wonderful spot depending on the weather and your desires. Secluded anchorages in Biscayne and Everglades National park and live music in a Tiki Bar are just a few of the possibilities.



Sailing, Snorkeling, Water Recreation

Average Visit Time

Full day, Multi-day


Group Discount

Fishing Type

Back Bay Fishing, Charter Captain, Inshore Charters

Guest Information

Family Friendly, LGBT Friendly