Key West is a lot of things. The Conch Republic. The end of the road, or at least the end of the 127-mile-long Overseas Highway. It’s irreverent, different, fun. And it’s colorful: Consider the daily scene where hundreds, or thousands, of people, plus various fire-eaters, jugglers and tightrope walkers, gather on Mallory Square to look for the green flash as the sun goes down. Or the annual Fantasy Fest parade (pictured above right) or the New Year’s Eve blowout (above left).
Most of all, Key West is a great cruising destination. If you’re looking for a weekend or more, head down from Fort Lauderdale after the show, spend the night in Marathon, half way down the Keys, and then tie up at one of the many first-class marinas in Key West; or forget Marathon and if you have a faster boat and just head for Key West directly. Over the years I’ve cruised there on everything from a Cigarette 38 to a variety of trawlers.
If you’re doing the Great Loop, take in the whole loop and cruise to Key West (instead of cutting across Lake Okeechobee). If you’re cruising to Cuba (as I did 20 years ago with Scott Porter, the president of Formula), Key West is the natural jumping-off spot for Havana.
Key West is fun any time of year, but this week it’s celebrating its annual Fantasy Fest, which ends Saturday, Oct. 27. This may be a little too off-the-wall for some tastes; the advertised events include the Dirty Doctors and Naughty Nurses Party and the Kinky Couple’s Party, but there are parades, with 50 floats heading down Duval Street, body-painting and some libations. Then there’s Halloween itself.
Of course, you can forget the Mardi-Gras-type scene and head for some great seafood dives, get a Margarita at Sloppy Joe’s, chill to the omni-present sounds of Jimmy Buffett, or wander over to Ernest Hemingway’s old house, where he wrote For Whom the Bell Tolls.
For a full description of what to do in Key West, here’s a great story from Coastal Living: