Sailing the Florida Keys – A How To Guide


Sailing the Florida Keys is a very popular thing to do among boaters. The keys are at the south point of Florida. They are a chain of islands 170 miles long that is embedded in turquoise water. Bordered by the unique living coral reef in the United States. The subtropical climate and the extraordinary beauty of the Atlantic have made this ecological wonder one of the most prized destinations for sailors.


Let's dive right in.


The Options for Sailing the Florida Keys

1. Leasing the Sailboat Without a Captain or "Bareboat Chartering"


The sea has no secrets for you or your crew and you are capable of bringing the sailboat back to port even if a hitch happens during your trip.

2. Chartering a Sailboat with a Captain


You prefer to have a captain on board to help you with the bowline knot.

3. Sailboat Training while Sailing the Florida Keys


You want to learn to navigate or you wish to enhance your knowledge while sailing the Florida keys. Charter companies offer courses at every level, for groups, couples, for a weekend or for the whole week.

4. Cruising with a Captain and a Cook


You watch them raise the sails and manipulate the sauce pans, while you take it easy.


Choosing a Sailboat for Sailing the Florida Keys

The marinas cannot always accommodate boats that are too big. Also the draft of your boat should not exceed 4.5 to 5 feet and the beam 13.5 feet to 14 feet. They prefer mono hulls from 40 to 43 feet long.


With boats of this configuration you can combine space and comfort and should be able to find a spot in the small marinas of the Keys. These boats are also better equipped than the smaller sailboats for sailing the Florida keys. Catamarans rarely find a dock large enough to accommodate them and must anchor outside of the marinas.

Boats can be rented for a day, a weekend or for a week to go sailing the Florida Keys.

The Best Time to Go Sailing

The Keys benefit from a subtropical climate. You can sail all year round but, like everywhere else, there is a fantastic time of the year and less favorable times.

The best times to go sailing the Florida Keys are: March, April, May, end of November and beginning of December.

The dates of high tourism are Thanksgiving, Christmas, and New Year's.

Possible cold front periods: End of December, January and February.
Hurricane, humidity and mosquitoes' months are June to November, with a peak in August September, and October.

Books on Sailing the Florida keys

Cruising Guide to the Florida Keys, by Captain Frank Papy

Good basic information for sailing the Florida Keys. It explores places to visit, marinas, underwater activity, etc. Excellent maps describing the entrances to ports and marinas. It points out the difficult places to access because of shallow waters.

Diving and Snorkeling guide to The Florida Keys, by John Halas, Judy Halas and Don Kincaid

Excellent guide for skin diving and snorkeling. Description of coral reefs, exotic fish and sunken Spanish Galleons. Indication of depth and the level of difficulty of the different dive sites.


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