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Island Dreamer Sailing
American Sailing Association
Classes and Certifications

Join us living aboard our 41’ Morgan Out Island sailboat for a multi day trip to really learn how to operate and live on a sailboat. Beginners will spend time sailing our 20’ sailboat to learn the basics, then we will head down into Biscayne Bay to the Keys. We anchor at a new place each night based on the weather and your preferences. Meal preparation is included so you can focus on learning. All our trips are private charters, you will have your own cabin and head with shower.


We believe American Sailing Association certifications are important. Depending on your previous experience, the following course certifications can be earned on your trip. More information about each course can be found on the right side of this page. Students should figure 2 to 3 days per ASA level, we will work at your pace to assure a through understanding of the material.



You will have lots of time at the helm working with your partner to navigate, plan the evenings anchorage, and become comfortable docking the boat. With two captains on board you will have lots of personal teaching time, with two different approaches to helping you learn . You will have time to practice driving the dinghy, with time to get ashore for a walk at a park or live music at a “tiki bar”.


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.


Daytime Group Lessons (Non- Liveaboard):

Includes books and membership in ASA

                                   First Student   Additional Students

Basic Keelboat (101)            $  995        $   495

Basic Costal Cruising (103)  $  995        $   495

Bareboat Chartering (104)  $1,412         $1,112

   Lunches and 1 dinner are included and a 1 night night stay is both required and included.

Coastal Navigation (105)            Please Inquire

Advanced Costal Cruising (106) Please Inquire

Radar Endorsement (120)          Please Inquire




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.

American Sailing Association Classes We Teach:


Basic Keelboat (ASA 101)

Prerequisites:  None

General Description:  Able to sail a boat of about 20 feet in length in light to moderate winds and sea conditions in familiar waters without supervision. A preparatory Standard with no auxiliary power or navigation skills required. This class will include time on a 19' to 30' Keelboat.


Basic Coastal Cruising (ASA 103)

Prerequisites:  Basic Keelboat Sailing Certificate

General Description:  Able to cruise safely in local and regional waters as both skipper and crew on an auxiliary powered sailboat of about 20 to 30 feet in length, in moderate winds and sea conditions.


Bareboat Chartering (ASA 104)

(Intermediate Coastal Cruising)

Prerequisites:  Basic Keelboat Sailing and Basic Coastal Cruising Certification

General Description:  An advanced cruising Standard for individuals with cruising experience. The individual can act as skipper or crew of a 30 - 50 foot boat sailing by day in coastal waters. The Standard includes knowledge of boat systems and maintenance procedures.


Coastal Navigation (ASA 105)

Prerequisites:  None

General Description:  Able to demonstrate the navigational theory required to safely navigate a sailing vessel in coastal or inland waters. There is no Sailing Skills part to this Standard and practical application of this sailing knowledge is found in the Advanced Coastal Cruising Standard.


Radar Endorsement (ASA 120)

Prerequisites: Coastal Navigation

General Description: The ASA radar course teaches safe, efficient use of small-craft radar for piloting, chart navigation, and collision avoidance, including radar principles and  practical matters of radar operation. A realistic PC based radar simulator is used in the course to illustrate radar measurements.


Advanced Coastal Cruising (ASA 106)

Prerequisites: Basic Keelboat Sailing, Basic Coastal Cruising, Bareboat Chartering and Coastal Navigation Certification

General Description: Able to safely act as skipper and crew of a sailing vessel about 30 to 50 feet in length. This is a day and nighttime Standard in coastal and inland water, in any weather.