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Island Dreamer Sailing
Liveaboard Lessons

Learn the skills you need for cruising while living aboard our sailing sloop, Island Dreamer, a 41’ Morgan Out Island. In a friendly setting where no yelling is allowed, you can practice the cruising lifestyle. Learn about sailing, anchoring, docking and boat systems while exploring the protected waters of Biscayne Bay and the Florida Keys.  We anchor in a new place each night and your sailing holiday is a private charter.

Couples  and Families will enjoy working directly with Captains Margie and Harold in order to build confidence and learn about sailing and boat handling. You decide whether the sailing lessons or ASA Certification classes should be informal or more structured. You can earn certification if you like; or you may simply want to enjoy sailing, fishing, swimming and snorkeling in the unique part of the USA that is the Florida Keys.

Margie and I have been exploring and learning about the Florida Keys for the last 27 years. We will be happy to share with you our knowledge of the reef ecology and the history of the keys. We can also share our snorkeling and fishing spots–-maybe we’ll even catch a lobster for dinner.

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.


 certifications also included.


Trips:   Charges are based on days out on the water sailing.  It may be possible to spend the night before your trip starts and your last night aboard at $75 per night.  Dinners are not included those nights. Shorter or longer trips are available. Please call for additional pricing.

Payment:  50% deposit is required in order to confirm your charter, with the balance paid 14 days before sailing. Cash, checks and credit cards accepted.

Rates:  Based on double occupancy and include provisioning and meal preparation. Please add $125 per additional guest per day.

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.