Island Dreamer Sailing School (305) 283-7283

Join us in Miami and the Florida Keys for an all-inclusive, multi-day liveaboard trip or a private daytime class. We specialize in teaching couples and most of our trips are taught by couples who are both captains and instructors. All ASA levels from Basic Keelboat to Offshore Passagemaking and Catamaran certification are offered. Docking Endorsement and ASA challenges are also available. We offer easy going instruction in the clear, calm waters of Biscayne Bay; or sail with us in the Bahamas, Eastern Caribbean and Greece. Make memories that you will treasure for a lifetime.

Come with us on our private charters that are scheduled to meet your needs. During our trips, meals are prepared for you so you can relax and learn to sail. We anchor in a new place every night as we show you how to choose the best locations based on the current weather predictions and your personal interests. Swimming, snorkeling and a little onshore exploring are available. Many secluded anchorages can be found in the protected waters of Biscayne Bay and the Florida Keys National Marine Sanctuary. On the other hand, live music, a waterside Tiki bar and a seafood dinner ashore might be more to your liking.

Our ASA sailboat lessons can be geared specifically for couples, families or singles. Learn how to make sailing a relaxing, enjoyable experience. Beginning sailors practice their basic skills on our 20′ keelboat and then move up to our larger cruising boats to learn about anchoring, docking, navigation and boat systems.

Our couples courses are focused on showing you what life is like on a cruising sailboat. We specialize in one-on-one instruction on a private charter where you live onboard with one of our captain couples, both of whom are experienced instructors with years of cruising knowledge. Couples teaching couples is an innovative way for you to build confidence in each other through personalized instruction in an easygoing, positive environment. Our supportive approach allows you to build your skills at your own pace and to share in the decision-making process in order to make sailing comfortable for everyone.

Other advanced programs are available. You may want to join us on an ASA 114 Cruising Catamaran certification trip in the Florida Keys or in the Abacos, Bahamas. Our ASA 106 classes include a night sail and are done on cruises in the Keys, in the Spanish Virgins or from Aruba through Curacao to Bonaire. ASA 108 Offshore Passagemaking trips go from St. Thomas to Aruba or from Bonaire to St. Thomas for 450 miles of sailing on a well-equipped Hylas 47′.

Join us in Greece or the Bahamas for crewed, week-long charters. Or you can rent a bareboat for “flotilla” sailing in tandem with us in these beautiful areas before setting out on your own. We have well maintained boats available along with lots of “local knowledge” about harbors, anchorages and Med. mooring.

ASA Sailing Certification Courses Offered

ASA 101, Basic Keelboat Sailing
ASA 101, Basic Keelboat Sailing
Learn to skipper a 20' - 27' sloop-rigged keelboat by day, in light to moderate winds and sea conditions. Learn basic sailing terminology, parts and functions, helm commands, basic sail trim, points of sail, buoyage, seamanship and safety including basic navigation rules to avoid collisions and hazards.
ASA 103, Basic Coastal Cruising
ASA 103, Basic Coastal Cruising
Learn to skipper a sloop-rigged auxiliary powered 25'-35' keelboat by day in moderate winds and sea conditions. Learn cruising sailboat terminology, basic boat systems, auxiliary engine operation, docking procedures, intermediate sail trim, navigation rules, basic coastal navigation, anchoring, weather, safety and seamanship.
ASA 104, Bareboat Cruising
ASA 104, Bareboat Cruising
Learn how to sail a sloop-rigged, auxiliary powered 30'-45' sailboat during a multi-day cruise upon inland/coastal waters in moderate/heavy winds and sea conditions. Learn about provisioning, boat systems, auxiliary engines, advanced sail trim, coastal navigation, anchoring / mooring, docking, emergency operations, weather, and more.
ASA 106, Advanced Coastal Cruising
ASA 106, Advanced Coastal Cruising
Learn to safely act as skipper and crew of a sailing vessel about 30 to 50 feet in length in coastal and inland waters, in any conditions.
ASA 108, Offshore Passagemaking
ASA 108, Offshore Passagemaking
Learn to skipper a sailing vessel on extended offshore passages requiring celestial navigation. Knowledge of long-term passage planning, offshore vessel selection, sail repair, offshore first aid, watch-keeping, emergency procedures, abandon ship protocols, safety and seamanship.

Learn to skipper a sailing vessel on extended offshore passages requiring celestial navigation. Knowledge of long-term passage planning, offshore vessel selection, sail repair, offshore first aid, watch-keeping, emergency procedures, abandon ship protocols, safety and seamanship.
ASA 114, Cruising Catamaran
ASA 114, Cruising Catamaran
Learn to skipper an auxiliary-powered sailing cruising catamaran of approximately 30-45' feet in length during a multi-day liveaboard cruise upon inland or coastal waters in moderate to heavy winds (up to 30 knots) and sea conditions.
ASA 118, Docking Endorsement
ASA 118, Docking Endorsement
Learn basic docking skills for boats with single inboard or outboard engines. Discover the basic theory and hands-on techniques needed to dock and undock boats in an efficient manner and without damage or injury.

Other Services Offered

  • Women Only Courses
  • Couples Courses
  • Private Courses
  • Weekday Courses
  • Weekend Courses
  • Corporate Team Building Courses
  • ASA 'Challenges'
  • Day Sail Charters (public)
  • Sunset Cruises

ASA Veterans Sailing Education Program

At ASA we recognize the sacrifices made by the brave men and women who have served or are serving in our country's armed forces. As a token of our appreciation, and our way of saying thank you, we are inviting veterans and active military personnel to share our passion for sailing by offering a discount on our ASA 101 Basic Keelboat Sailing course.
Island Dreamer Sailing School is offering a minimum of $50.00 or 10% off their ASA 101 Basic Keelboat Sailing course.

Sailing School Reviews / Testimonials

  • 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. [read more]

    Tom G. - ASA 101, Basic Keelboat Sailing

  • Captain Derrek and Captain Stephanie were great teachers and hosts on the Morning Dance! We booked a 7 day trip to complete 3 levels of ASA certification. My husband and i were excited to do this together with another couple.[read more]

    Tammy Campion - ASA 104, Bareboat Cruising

  • My trip with Island Dreamer Sailing School was amazing, they did an excellent job of the instruction, food, etc. I would recommend them strongly for captained charters and courses.[read more]

    Kevin James - ASA 103, Basic Coastal Cruising

  • We have sailed with Captains Harold and Margie three times. They gave us the convince to buy a boat and we have crossed the Gulf Stream four times now. You will not get a more knowledgeable team. Looking forward to sailing with them again. [read more]

    Bob Montgomery - ASA 106, Advanced Coastal Cruising

  • 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.[read more]

    Wes N. - ASA 103, Basic Coastal Cruising

Contact Information

Island Dreamer Sailing School

Address 1900 N. Bayshore Drive Suite 1AMiamiFL33132United States
Phone (305) 283-7283
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