Learning to Sail in the Florida Keys

By: Cruising Tips, Destinations, Learn To Sail, Schools

Sailing In The Keys

Let’s go straight for the cliches and talk about the Conch Republic and a salty life and toss in flip-flops while you are at it. In a world away from everywhere the Florida Keys stands out as an outpost for the rest of us. The Florida Keys calls to people who would rather disregard responsibility and embrace the sensibility of not being sensible.

In other words, if you fantasize about boat life or you just want to spend time near the water, the Keys might be calling you. If you want to learn how to sail there are quite a few places in the Florida Keys where ASA courses are taught and where you can combine a getaway with enhancing your sailing education.

Things To Do In The Florida Keys

Key Largo

The initial impression of the Florida Keys often is defined by Key Largo as it is the closest and largest island to the major metropolitan area of South Florida. Tourists flock to John Pennekamp Coral Reef State Park to snorkel and SCUBA dive while fishermen dream of catching the “big one” on a fishing charter from Key Largo. You can book an underwater hotel room at Jules’ Undersea Lodge if you are into sleeping 30 feet under the surface, however, you will have to SCUBA dive to your bed. While in the Keys seafood is king and conch salad is a must do.



Tavernier is technically still in Key Largo, but since the Blond Giraffe Key Lime Pie Factory is located here it must be mentioned on its own. You need some key lime both before and after you sail the Keys. While you are at it explore the area and head down to Mile Marker 88 and find the spot on the beach with cold drinks and the great view. The Florida Keys can deliver with good sailing but don’t forget it specializes in picturesque sunsets.



This section of 13 islands of the Florida Keys is known for a Dolphin Research Center and the ability to explore nearby islands by boat. You’ll want to drive over the seven-mile bridge just to say you have and take some time in the Florida Keys National Marine Sanctuary where they work to protect more than 2,900 square nautical miles of Florida Keys coastal and ocean waters.


Key West

When you make it to the southernmost point in the continental United States you’ll take a walk along Duval street, you’ll linger in Mallory Square and you’ll probably have a Hemingway Daiquiri with a view of the ocean. The pace is laid back in the Keys so don’t fret if things don’t move as fast you’d like. You can stay at the Margaritaville Key West Resort and Marina if you feel like you don’t get enough Jimmy Buffet in your daily playlist. Visit the Hemingway House to learn a bit more about one of America’s most misunderstood authors or grab a boat and sail out to the Marquesas and explore the Key West National Wildlife Refuge.



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Jon Barrie
Jon Barrie

Are there any charter boat opportunities out of the keys for either sailing or power? My wife and both have our license dating back to when we had a 40′ sailing cat…