City Snap Guide: Key West

Key West, America’s southernmost city, is quirky, fun and eminently gay-friendly. Once you arrive, you’ll feel removed from the rest of the Sunshine State in this paradise of particular charm. Stroll palm-lined streets to discover gingerbread mansions, tin-roofed conch houses, open-air bars and sidewalk cafés. Walk in the footsteps of Ernest Hemingway, Harry Truman and Tennessee Williams. Visit the renovated Historic District, known locally as the Key West Bight, and arrange a day on the water to fish, snorkel or scuba dive.

Hemingway’s Glory Days

On July 21, coinciding with Ernest Hemingway’s birthday, you’ll see Hemingway doubles everywhere. The Pulitzer Prize-winning author left an enduring legacy in the city, commemorated during the annual six-day Hemingway Days celebration. Catch a reading during the festival and get a book signed by an acclaimed author, or watch stocky white-bearded men vie to win the look-alike contest. Year round, you can visit the Whitehead Street house, built in 1851, where Hemingway lived in the ’30s. Above the pool house is a separate writing studio where the novelist penned To Have and Have Not and polished the initial draft of A Farewell to Arms.

Key Lime Pie and Cool Cocktails

Pop into Sloppy Joe’s, a beloved drinking spot since 1937 that pours a steady stream of cocktails from 9:00 a.m. to 4:00 a.m., located at the corner of Greene and Duval streets. Visit Better Than Sex and try it’s Kinky Key Lime pie, a fluffy lime chiffon creation with macadamia nuts. This romantic dessert spot dips its wine glasses in chocolate to better match the decadent warm brownies, peanut butter pies and ‘Sugar Daddy Cheesecakes.’ Be sure to have a nosh at B.O.’s Fish Wagon. It started out as a catering truck, serving what many locals believe to be the world’s best fish sandwich, but the burgeoning ranks of fans prompted the purveyor to build a restaurant – modelled after the original truck. Just step up to the counter and order.

Sunset Celebration

Head to Mallory Square just before sunset to witness the famous celebration of the setting sun. About two hours before the sun dips below the Gulf of Mexico, masses of locals and tourists flock to the water’s edge to catch the nightly arts festival. Join in and watch jugglers, magicians, escape artists and other streeet performers, get your fortune told by psychics or buy everything from jewellery to sculptures, paintings and objects d’art from local artists.