On Our Gaydar: Key West

Looking for a cold weather escape? Head south for the winter.

Posted by Natalie Hope McDonald on 11/19/2012 at 7:00AM | 1 Comment
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Photos courtesy of the Key West Gay & Lesbian Convention & Visitors Bureau

This almost six-square-mile island has become a destination of choice for gay snowbirds. Not only does Key West have its share of eye candy year round (think white-washed architecture and handsome beach bums), but the sparkling vista has been influenced by everything from rich Cuban culture (it’s just 90 miles away) to the literary lore of Ernest Hemingway and Tennessee Williams, who penned some of their most famous works in this artsy coastal community.

Play
New York has its big shiny ball, but every New Year’s Eve a drag queen named Sushi is lowered from atop the Bourbon Street Pub in a big red stiletto (724 Duval Street, 305-294-9354). Yes, Key West is that gay. The bars and restaurants along Duval are the ultimate places to see and be seen. Ernest Hemingway is considered a native son, and his home (with its famous six-toed cats) is still one of the most popular attractions—for good reason (907 Whitehead Street, 305-294-1136). Looking for some schooling on local gay history? The Key West Gay & Lesbian Museum and Archive tells the story of Southern LGBT life—including that of Richard Heyman, one of the country’s first openly gay mayors (513 Truman Avenue, 305-292-3223).

Shop
Skip the tacky t-shirt shops and head for the Clinton Square Market (291 Front Street, 305-296-6825). Sure it’s touristy, but you’ll find local merchants selling everything from island fashions to gourmet coffee and candy. Cigar making is also a big deal here—visit the area known as Cigar Alley and the multitude of shops along Duval selling fat hand-rolled stogies. Pick up some art from Haitian Art Co. (605 Simonton Street, 305-296-8932) or Cuba! Cuba!, where colorful original paintings line the walls (814 Duval Street, 305-295-9442). Or take home a printed porcelain tile from KW Light Gallery (1203 Duval Street, 305-294-0566).

Eat/Drink
The Orchid Bar at the Orchid Key Inn serves up creative elixirs alongside the lush pool garden, including martinis infused with local ingredients (1004 Duval Street, 305-296-9915). If craft beer is more your taste, The Porch specializes in a sophisticated selection of suds (429 Caroline Street, 305-517-6358). Or have a gay old time at 801 Bourbon Bar, where drag queens perform nightly (801 Duval Street, 305-294-4737), or at lesbian-friendly Aqua (711 Duval Street, 305-294-0555). The hotel La Te Da has three levels of entertainment, including a cabaret, restaurant and open-air terrace (1125 Duval Street, 305-296-6706).

Stay
The gay male resort scene is very popular here, making it tough for women to find a lesbian-friendly alternative. But Alexander’s Guesthouse is both gay- and lesbian-friendly, with whitewashed rooms and a beautiful pool and spa area (1118 Fleming Street, 800-654-9919). Pearl’s Key West also caters to women (525 United Street, 305-292-1450), while The Island Guest House is just for men who like to show off their finest, um, assets—it’s been voted among the best (clothing optional) gay male resorts in the country (1129 Fleming Street, 800-890-6284). Prefer something more low-key? Cypress House is a historic B&B in Old Town—within walking distance of all the action—that offers a sophisticated experience on a former estate dating back to the late 1800s (601 Caroline Street, 305-294-6969).

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User Comments:


  1. Brian says:

    Okay, now that you’ve heard the good, let me tell you the bad:

    1. Construction: right now, Key West is undergoing a two-year road construction project to beef up the seawalls, storm drains, and the main drag (pardon the pun), Roosevelt/Truman Ave. As a result, the normally four-lane, two-way Roosevelt is now a two-lane one-way going into downtown Key West. The trip back out can be made on either Flagler Blvd or A1A, but be prepared for congestion, and please pay attention to road signs. It’s a bit overwhelming with all of the other signs that need to be paid attention to, but if your passenger can watch for whatever shop or hotel you’re looking for, that’ll free you up to watch out for the several points where the right lane becomes a turn-only.
    2. Military bases: okay, military bases in and of themselves are definitely not bad things, but you need to realize that there are several of them here in Key West, and they are all manned by gate guards. Please use some courtesy for the men and women who guard our nation, and don’t stumble onto a gate guard asking for directions to something. Although they will be kind and courteous and help you as best they can, a) it’s not their job, and b) you’re holding up a long line of traffic behind you that needs to get somewhere ASAP. If you see yourself heading for a military gate by mistake, turn around and get directions elsewhere.
    3. Snowbirds: again, don’t get me wrong; snowbirds are a good thing, but let’s face it. Motorhomes are large, ungainly creatures, and Key West’s roads are NOT large; in fact, most of the streets are pretty narrow. So be aware that you may get stuck behind one and be patient with the driver.
    4. Lack of, well, just about everything: Key West IS a HUGE tourist destination, but unless you’re into drinking, eating, watersports, paying way too much for touristy kitsch and not much else, it’s not the greatest. Keep in mind: there is no Walmart, no Target, no Mall. There is a rather tiny Sears and an outdated, miniscule KMart. There are also two Publix grocery stores. So far, the Publix stores are the only two on the island that even approach being in compliance with the American Disabilities Act; most stores do NOT have aisles wide enough to accomodate a wheelchair.
    5. Prices: just about everything in Key West is artificially inflated. The excuse is that there’s only one road in and out (US 1), and it costs more to ship everything down here. The truth is that everything in Key West is owned by about five established “families”, and they pretty much charge the “servants” (Key West has two industries: government and service) whatever they want to. The only exception to this is the T-Shirt shops on Duval Street, where everything is $5. Keep in mind, this especially applies to gas prices, which are generally $.50 higher per gallon than on the mainland.
    6. Mopeds/scooters/golf carts: Now, normally, I would say that this would be the ideal way to get around Key West, what with the heavy traffic due to construction and narrow streets, but these things are the bane of most motorists’ existence. The big problem is that there are a myriad of places where you can rent these things, and they are grossly underpowered. There IS a good reason for this: any scooter under 150 ccs in displacement does not require a motorcycle license to operate, and most tourists don’t have a motorcycle license. But the fact is, they still can’t do the general island speed limit of 25-30 mph, and it’s annoying.

    In conclusion, I’m not trying to scare anyone away from coming here; it really IS a lovely tourist destination. It’s NOT a great place to live, but I’ll be transferring soon, and I’ve found that a monthly trip up to Miami is actually worth it, so it doesn’t really phase me. But if you are planning a trip down here, you should take all factors into account, and be aware of what you’re in for once you get here.

    A Key West resident (for now)

 
 
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