Many dream of selling everything, buying a beautiful boat, and spending the rest of their lives sailing in the Florida Keys, and sailing under canvas to other tropical ports in the world. Unfortunately, we are not all in the position to do that. But fortunately, you can find plenty of opportunities to spend a day or two—or longer—enjoying that experience on your Florida Keys vacation.
There are numerous boat tours available for sailing all over the islands, with Key West sailing being the most popular. A couple on a honeymoon or romantic anniversary vacation can book a Key West sunset sail on a private yacht. There are authentic tall ships, such as those of the Liberty Fleet that are longer than 100 feet and carry up to 50 passengers, available for sunset dinner cruises. This kind of Key West sunset sail is excellent for weddings, corporate events, or family reunions. If you are not part of a group and still want this tall ship experience, you do not have to charter the entire ship. You just purchase a ticket, come aboard, and savor the experience with the other passengers.
Key West sailboat rental is possible for boats of all sizes. From little cats, meaning catamarans, to live-aboard vessels, you can find several types of sailboat options available. Several of the resorts have small one- and two-person sailboats, like the kind you often see in local sailing regattas with youngsters as the skippers in small harbors. Many of these resorts also offer sailing lessons, and this Key West sailing opportunity can occupy your children for days. There are, in fact, a few of the top-rated sailing schools in the country located in Key West, and teens can participate in a virtual summer camp at sea, living aboard a vessel as they learn to sail.
For travelers who are interested in a variety of things to do, Key West sailing often involves other water activities, as sailboats will drop anchor in prime snorkeling and diving spots, sometimes in areas that are good for dolphin swims.
Florida Keys sailing is not limited to Key West. Islamorada has a co-ed summer sailing camp, Florida Sea Base, with a minimum age of 13. Marathon Key and just about every other main island have sailing clubs and marinas. In many places, boats (either motorized or sail) actually come with vacation rentals. Next to Key West, sailing in Key Largo is probably the most popular, and there are several yacht clubs and sailing marinas. It's possible to charter both crewed and bareboat sailing vessels. A crewed vessel comes with an experienced captain and a crew as extensive as the itinerary and ship size allow. Bareboat means you get the boat only. For the latter, you have to pass certain financial and skill levels.
It is possible to enjoy Florida Keys sailing without staying anywhere on the islands at all. There are sailing vessel companies based in Miami and the Fort Myers and Naples area that go to Dry Tortugas National Park, stopping for a Key West sunset sail and perhaps a taste of the famous nightlife, and then on to Bimini and Nassau in the Bahamas. The ship sleeps six people in four cabins and will also do clothing-optional sails.