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Creating Confident Sailors with Easygoing Personalized Training

Family Vacations

Every charter on Island Dreamer is designed around the choices you make. There are a lot of things to do in the Florida Keys including exploring islands, fishing, swimming, snorkeling, visiting shore and just relaxing. We plan our daily activities around your preferences. We understand the need for kids to be active and try to pace our trip to keep them interested. Margie and I have spent the last five years working with the Boy Scouts of America at their High Adventure Seabase taking youth groups on 6-day liveaboard charters. We understand and enjoy working with all age groups.

Below is a note I wrote to one family describing some of the possibilities for our charters:

Life on a cruising sailboat does have some differences from sailboat racing. But at the end of day, I think you and the boys will get some of the same great feelings that only being on the water can provide. For excitement, Seeing a turtle or dolphin when you are on the reef snorkeling, taking a bicg boat under sail through a narrow pass or maybe even catching a lobster by hand at the start of season will generate plenty of memories.


I really enjoy sailing and navigating in the clear, shallow waters of the Gulfside of the Keys. You will learn to judge the water depth by the color and to sail with as little as one foot of water below your keel. You will be able to apply the knowledge that you have gained racing to handling a 25-ton boat under sail in tight quarters.

There is a real diversity of things to do and we understand the need of young boys for lots of "excitement." It's great to see the world through their eyes when they see a dolphin from the boat or a barracuda in the water for the first time.

Our charter rates are for the whole boat. All trips include full use of the boat, fuel, ice, fishing gear and license, dinghy, and of course, your licensed captains.  

USCG regulations allow us to carry up to six passengers. The private stateroom on Island Dreamer accommodates two adults. The settee in the main salon can be converted into a bed for two more adults. Sleeping spots for additional guests can be found, but we would only recommend this for families with children.

Our home port is located in Miami and is easy to reach. We provide free transportation from the Miami Airport to Island Dreamer. Added overnight stays on the boat at the beginning or end of your trip are dependent upon our charter schedule and may be available for a small fee.  

We will be happy to customize your trip, so please call us at 561-281-2689 with any ideas or questions you have.

          Inclusive Rates for Couples and Families

Includes provisioning, meal preparation and is a private charter. You should plan on one dinner ashore during the week at your expense. Guest cabin has a head and shower, linens provided.

Private family Sailing on a Monohull

 Trip Length           Rates Per Person

                    2 days                     1080       

                    3 days                     1390

                    4 days                     1860

                    5 days                     2080  

                    6 days                     2460       

                    7 days                     2840  

 Based on Double Occupancy

 Single Private trip supplement add 160 per day

 Over 2 people add 125 per day per person

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Private Family Sailing on a Catamaran

 Trip Length           Rates Per Person

                    2 days                     1230       

                    3 days                     1620

                    4 days                     2160

                    5 days                     2450  

                    6 days                     2910       

                    7 days                     3370

Based on Double Occupancy

 Single Private trip supplement add 160 per day

 Over 2 people add 125 per day per person

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.

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 $140 per night.  Dinners are not included those nights. Shorter or longer trips are available.  Please call for additional pricing.

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

Rates:  Live aboard rates are 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.  

week long family sailing trip with 2 kids on an all inclusive charter