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Island Dreamer Sailing
Couple taking sailing classes from iinstructors that are a couple
Couple to Couple
Sailing and Cruising Courses 
In the Florida Keys

Our captain couples teach you the skills you need to safely control a sailboat with hands-on, private one-on-one training. They will create a calm, “no yelling” environment while teaching both partners the fundamentals of sailing. The level of training you choose is geared to your abilities and desires.

Learn Sailing, boat handling, weather planning and navigation for enjoyable, safe cruising. In addition, you will gain the knowledge you need to choose the boat and cruising style that is right for you and your partner.

Dreaming of buying your own cruising boat? Want to rent  sailboats in beautiful sailing spots around the world? What you experience sailing with us will give you the tools you need to travel together under sail.

The time you invest in our training program in the Florida Keys will help you as a couple define your cruising goals and show you that living the dream can be drama-free.  

You and your partner may have different sailing styles and certain expectations of what enjoyable cruising can be. Let us help you work together to find the unique approach to living aboard that is right for you. We will show how you can work together to build confidence and trust in each other. View the possibilities of the cruising life style through the eyes of sailing couples that have been cruising together for many years.

We believe American Sailing Association certifications are important. Depending on your previous experience, the following course certifications can be earned on your trip.  One or both of you can work on certifications and we always work at your pace.

Join Captain Margie and Captain Harold or  Captain Jean and Captain Jeff leaving from downtown Miami and sailing into the calm, clear waters of Biscayne National Park on your way to the Florida Keys. The shallow waters of the Keys are a perfect place to learn the fundamentals of sailing. We start on our responsive 20’ keel boat and then move up to the stability and simplicity of our 41’ sloop rig where you will learn the many facets of coastal cruising. Margie and Harold are both USCG licensed captains and Harold is an ASA sailing instructor.  Jean and Jeff are both USCG licensed captains and ASA sailing instructors. Jean is an accredited marine surveyor and Jeff is an electrical engineer.

Liveaboard Rates and Lessons

Includes provisioning, meal preparation, lessons and is a private charter. Guest cabin has a head and shower, linens provided.

Sailing In The Keys

            Trip Length           Rates (Total for 2 Persons)                                                                                    

                    4 days              $3,592

                   5 days              $3,672     

                    6 days              $4,282      

        Additional days              $  680

Click to View Current Specials

ASA Certification adds $125 per level, per person, and includes the cost of books and membership in ASA.

 

Explore some of the 150 mile chain of islands, including remote anchorages seldom visited by cruising boats in Biscayne and Everglades National Park.  Take the time to really learn what living aboard is like.

 

Cancellation:  If you cancel the charter, the fees are not refundable unless the vessel is re-booked by another party. If we are able to re-book a charter for the same dates, the deposit will be refunded less a 10% fee. If you need to change your booking dates, a fee may be charged. We strongly recommend trip insurance to cover unexpected circumstances. If a trip is canceled due to weather, we will refund the fees for the unused part of your trip.

Alcoholic beverages:  Not included in charter fees. Shopping at a local liquor store upon your arrival can be arranged.

Sales Tax:  Florida Sales Tax of 7% will apply to the above prices if required. The charge for chartering any boat or vessel, with the crew furnished, solely for the purpose of fishing is exempt from Florida Sales Tax.

Gratuity:  After your charter, if you feel we have done a wonderful job, a gratuity is welcomed and always appreciated.  

partners taking sailing and cruising lessons