July 21 is Ernest Hemingway's birthday, and cool Key West, where the literary legend lived for a famous while, celebrates with Hemingway Days July 17-22. If you haven't been to Key West, put it on the list -- and now is a good time to go; tourists are mostly toast (except those there for the Papa Hemingway lookalike contest, of course) and the weather is fine -- island breezes keep you cool while traveling the currently quiet streets via conch cruiser.

Let's face it -- the festival is really just an excuse to visit Key West. Drive, don't fly -- our road trip over Florida's Alligator Alley and down the Keys on A1A to the US' southeasternmost point (is that Cuba in the distance?) is one of the best we have ever made, despite being dead broke and subsisting on purloined grapefruit from darkened yards. We ended up staying for a winter, seduced by soft wind and night blooming jasmine into sort of forgetting life was going on anywhere else.

If you go to Key West

Key West's (basically) one public beach, Smathers Beach, is social fun, but sand is skimpy, as the Florida Keys are coral islands, and not the reason to go: that would be having a grouper sandwich "all the way," music at Sloppy Joe's (you've gotta see it, and remember that beverage service starts very bright and early), and oyster raw bars. With daytime air and water temperatures around 80, visitors will want to get outside, but you may prefer to rest with a cafe Cubano (espresso and sugar) or mojito every 100 yards or so. Key West is not about over-exertion, though snorkelers will find undersea paradise in the clear water (head out to the Dry Tortugas for a day), and a little hunting will turn up uncrowded beaches if that's your bag -- the outdoor action's better from a boat. I believe the most strenous activity in which I engaged, aside from falling off windsurfers, was parasailing, and floating through the air in a harness hooked to a ski boat while admiring the water color below is not exactly hard.

Smathers Beach works for sand-strutting or waiting for windsurfer rentals, but the places to be have roofs, though not always walls -- those with both may require vouching from a local friend (easy to make) before vigilant bouncers let you dance. Get to the clubs by conch cruiser -- fat tire bikes with baskets where you should keep a flashlight, which may make you look like a local and will show you the way home to your guest house, which are among the most interesting Key West temporary addresses.

The gay scene in Key West cooks year 'round (About's Guide to Gay Life, Ramon Johnson, reports that PlanetOut rated Key West the number two gay resort town in 2006, and it's certainly a hot spot for gay spring break). A tourist-must is watching the sunset, or, more accurately, watching the sun set, at Mallory Square, when everyone applauds the moment it touches the horizon. October's Fantasy Fest is another fine time to visit -- in fact, the night we landed on the island was a Fantasy Fest weekend, unbeknownst to us, and it was a walk on the wild side. You can think some thoughts and see some things. Craazy. Key West's live and let live legacy, which includes a shady pirate past, lives on -- Key West welcomes travelers from every walk of life without question; some are coming to the end of the road for good reason and some are just rocking it for a season.

Its fiercely independent residents declared Key West to be in the mythical Conch Republic a couple of decades ago, post traumatic Keys-road-block incidents, which would be a secession from the US of A -- that should give you some idea what life just past the tourist curtain can be like. (Conchs, aside from being one name for human Key West natives, are shelled sea creatures eaten in every imaginable form in the Florida Keys. You must eat conch chowder, but do add butter and Tabasco and do stop chewing the conch after 45 seconds or so.) Conch secession didn't happen, of course, but it demonstrates what sort of folk are attracted to this funky, charming slice of life at the end of the road.

• Dawn Henthorn's Key West travel guides
• Hemingway Days in Key West
• Kay West Hemingway Days official site

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