It takes about four hours to fly to Key West, Fla., depending on the length of your likely layover in Miami, but once you arrive on this palm tree-studded island, you'll feel like you've landed in another world. The mix of steamy temperatures, relaxed island attitudes, colorful European architecture and Caribbean-influenced cuisine can make U.S. visitors feel like they've actually travelled much farther to a foreign country. That "far-away" vibe makes Key West an ideal location for a quick, but rejuvenating, getaway.
Unlike much of Florida, Key West is extremely gay-friendly. In fact, there are at least two gay bars on the main drag, Duval Street, and the island plays host to several gay and lesbian festivals every year. There are just a couple of things to keep in mind about travelling to Key West. Number one, it's hotter than you think, and SPF 30 is no match for that Southern sun. Plan on taking it easy, staying hydrated and reapplying sunscreen frequently. Secondly, locals will warn you that Key West isn't known for its beaches. That may be true, and they are admittedly a bit rocky. However, the views are stunning and there are warm white sand, palm trees and turquoise waves crashing on the shore—enough to please any landlocked Chicagoan.
The very first thing you should do when you arrive in Key West is rent a moped. They're abundantly available for about $35 a day, and are definitely coolest way to see the island. Once you've got your moped, it's kind of hard not to have a good time in Key West, but here are a few tips to get you started.
What to do
—Key West holds the distinction of being the Southernmost point on the continental U.S. ( it's connected to mainland Florida by long highways ) . In fact, it's only 90 miles away from Cuba. You can't actually see Cuba, but it's a cheap thrill to get your photo taken in front of the "Southernmost Point" marker at the end of the island.
—Snorkeling, jet-skiing, parasailing, scuba diving, taking in ocean views on a glass-bottomed boat or enjoying the sunset on a booze cruise—all variety of water adventures are available in Key West. Dedicate one day to seeing the island from the water.
—I have a pretty strict policy against going to museums on vacation ( or any time, for that matter ) . I think they're boring, and I'd rather experience a culture by immersing myself in it than by viewing in a glass case. That said, Key West's Butterfly Conservatory is amazing. There are hundreds of huge, Technicolor butterflies soaring around a fragrant floral conservatory. If you stay still, butterflies will land right on you. A visit to the Butterfly Conservatory is guaranteed to bring out the kid in anyone.
—Duval Street, Key West's main drag, is filled with shops, restaurants and bars, with plenty of opportunities for people-watching. Spend an afternoon browsing the shops, which range from kitschy souvenir stands and funky clothing retailers to upscale jewelers and art galleries. Don't miss Fast Buck Freddie's, a gay-owned store where you can find furniture, clothing; upscale bath products like Key West sea salt body scrubs; and lots more. Plan to stop for a cool refreshment. I recommend the peanut butter gelato at Gelato on Duval or one of the many frozen boozy concoctions at Fogarty's: The Flying Monkey.
How to party
—After the sun makes its breathtaking descent into the Atlantic Ocean, Key West parties well into the wee hours. The center of the island's nightlife takes place on Duval Street. Aqua Nightclub and Bourbon Street Pub cater to gay clientele with nightly drag shows and tanned and toned boys dancing on the bar. Try one of Aqua's glow-in-the-dark electric blue cocktails—and then switch to a more dignified libation.
—Pearl's Key West is a charming lesbian-owned guest house. Everyone's welcome, but Pearl's definitely caters to the ladies. Relax by the pool with a Key Lime Cooler, a tart, creamy cocktail that will cool you off and slow you down. You'll find Key limes in every imaginable form: pie, shots, ice cream, covered in chocolate on a stick—you name it, but Pearl's Key Lime cooler is the absolute best use of the island's eponymous fruit.
—If you're looking for a more laid-back happy hour, grab a table at a colonial-style patio gracing the front of many of Key West's bars and restaurants. Grand Café's elegant patio provides a birds-eye view of the Duval Street debauchery in a relaxed atmosphere. It has an impressive wine list and is open late for dinner.
—For a cheap beer and a lesson in Key West's rich history, head to Captain Tony's. The dark and divey saloon was formerly Sloppy Joe's, where Ernest Hemingway is rumored to have spent many an evening throwing back scotch and sodas. Captain Tony's is probably one of the only bars where you'll find a huge old tree growing right in the middle of it. Legend has it that many people were hanged from that tree, and the original owners didn't want to risk a run in with ghosts by chopping it down.
Where to eat
—Seafood is obviously the local specialty in Key West, and A&B Lobster House is the quintessential place to get it. Situated just a stone's throw from the water, A&B offers stunning views of the marina outside and refined steakhouse ambiance inside. Book a table on the veranda and order the surf & turf. It's a pricy night, but well worth it.
—For a lively dinner on Duval, check out Mangoes, which serves "Floribbean" cuisine on a patio that is both beachy and sophisticated. Start with an order of conch ( pronounced conk ) fritters, fried snail meat so popular they could be the French fries of Key West. Mangoes fries them up just right.
—Grab a light lunch with the locals at La Creperie, an adorable spot that churns out light-as-air, savory crepes stuffed with fresh fillings like prosciutto; egg and Swiss or Brie; and smoked salmon. Save room for a dulce de leche dessert crepe.
—Adventurous travelers will want to get off the beaten path for a low-key dinner at Hogfish Bar and Grill, a no-frills place that locals flock to for some of the freshest fish in town. Hogfish is located on Stock Island, which is a 20-minute moped drive from Key West—and well worth it for their namesake Killer Hogfish Sandwich. Grab a picnic table outside and watch the sunset over the marina with a couple of Key West Sunset Ales.
—If you can't afford a room at Casa Marina, a stunning Waldorf Astoria resort, indulge in a meal at the hotel's Sun-Sun Beach Bar and Grill. The views from this waterfront eatery are unmatched. You know the overused tropical-beach scene computer screensaver? Well, this has got to be where they shot that photo and, in person, it is truly breathtaking. Order fish tacos and a pina colada—and just sit back and enjoy the view.
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Key West, Florida. Photos by Shira Kollins
