Key West: Top Five


Poised at the end of a chain of islands, swishing Nike-logo style southwest from the southernmost tip of Florida, Key West has, for decades, been welcoming gays, lesbians, bohemians straights, and others that are simply fed up with the day-to-day grind in much of the rest of the world. It’s not that there’s no grind here — in fact, many locals work multiple jobs to pay the bills (island living can be expensive). But it’s a much more pleasant rhythm when the commute is atop two human-powered wheels; the jobs may include one or more artistic pursuits; and evening conversation usually includes a discussion of the sunset. (Trust me that does not happen often in New York City!)

As a gay resort destination, this Caribbean getaway (the self-styled Conch Republic once declared its independence from the U.S.) has seen its share of ups and downs, but is currently on a sustained and tantalizing upswing. Today’s buzzword is sophistication. Many hotels and guesthouses have benefited from significant upgrades. Several LGBT guesthouses, like the gay- and lesbian-popular Alexander’s Guesthouse ( are among the best on the island (gay or straight).

There is a plethora of exciting and buzzed about new dining options. And you can officially toss out that souvenir plastic margarita to-go cup you pocketed during your last visit: Key West is now home to a growing number of swank new cocktail and wine bars. The best news is that these establishments are not attempting to impose New York or LA in the Keys. They feel as organic and natural as a sunset on the beach. Key West offers LGBT visitors a wide range of options from trusted-and-true to new-and-sophisticated. Here are a few I highly recommend based on a recent visit.

Stay in
The Island House Key West  is an upscale and impeccably clean guesthouse for gay men with an all-inclusive resort feel, a convivial bar area by the pool, and a restaurant serving delicious food at almost any time of the day or night. There’s a small but well-equipped gym. The service is topnotch: professional, informed, and incredibly friendly. The resort is known for its sexual temperature with two whirlpools and a dark room at the hotel. Yet it’s also a spot that offers a romantic setting for a couple or a friendly atmosphere for a solo traveler wishing to make new friends. Many guests never leave the resort and have a great time, though we highly recommend enjoying all the surprising attractions you’ll find on the island.

Eat out
It is incredibly difficult to narrow down the wide range of terrific Conch Republic dining options to one or two choices. That said, two stand out from my recent visit. Nine One Five ) has been open since 2002 and gets justifiable praise for its Asian-flavored seafood and décor. But my new recent favorite is the more recently open Flaming Buoy Filet Co.. Open just over a year, the Flaming Buoy is owned and operated by (openly gay) partners Fred Isch and Scot Forste. The décor — 10 rustic wood tables and simple lighting — reflects the restaurant’s approach to dining: simple and fresh.

Drink up
You can still guzzle gigantic watered-down rum- or tequila-based cocktails anywhere along Duval St. But what’s new and exciting is the island’s burgeoning, sophisticated cocktail and wine bar culture. Check out the diminutive Orchid Bar , where mixologists take their drinks very seriously. The crowd is low key, and the space overlooks an illuminated pool: perfect after a busy day doing, well, nothing. The Porch is a wine and artisinal beer bar that has been open since summer of 2010 in a gorgeous old Victorian mansion.

One of my favorite events in Key West is free; happens every evening that it’s not raining; and is basically a pagan ritual. The crowds of hundreds (if not in the low thousands) of tourists who gather every evening to watch the famous Key West sunset — libation firmly in hand — probably aren’t consciously aware they are practicing a form of worship older than any organized religion: Toasting the setting of the sun. It’s fun to join the tourists once for this diurnal event at Mallory Square but on a subsequent evening, join the in-the-know set for a more mellow form of sun worship at Louie’s Backyard Afterdeck Bar, with its rustic wooden patio that faces west toward the setting sun.

Pump up
Visitors and tourists alike tool around on bikes. It’s the best way to zip around the island; it’s inexpensive; and the bike rental companies offer drop-off and pick up services at hotels. Two good rental companies are Eaton Bikes  and Re-Cycle . Now, hop on those bikes and hit the town! You can easily and quickly loop around the island, which is nearly completely flat. There are bike paths on the major streets. Be sure to take in the Key West AIDS Memorial embedded in the walkway approaching White Street Pier at the Atlantic Ocean, and check out Fort Zachary Taylor Beach  and the very cool frequently changing outdoor sculpture exhibit.

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