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Mike Diamond: Kiki-ing in Key West, with Video!

I packed very badly for my first trip to Key West; I forgot to bring flip flops, sunblock and my big floppy gardening hat. What the hell was I thinking? On some level I must have intuited that the magic of Key West would kick in and everything would work itself out. Or perhaps it was the fact that any of those items can be purchased at the hundreds of tourist friendly shops and kiosks that dot this tropical little village. At any rate, I didn't get sunburned and I had a fabulous time!

Key West is the last island in the chain of the Florida Keys, and claims to be the only frost-free city in the continental U.S. That is borne out by the gorgeous tropical plants that are everywhere one looks; swaying palms, colorful orchids, bromeliads and lush ferns; it's as if almost every street in town is its own little botanical garden. Situated 160 miles from Miami, and 100 miles from Cuba to the South, it is a wonderfully isolated locale, and has developed its own rich, strange and totally original way of life. The official motto of town is "One Human Family," a testament to the accepting, life-affirming vibe of the place. It goes beyond just "live and let live" and more like "anything goes." Fly that freak flag honey! There's a palpable energy here of exploration, and artistic and personal self expression; there is also a generosity and community-mindedness one doesn't often find elsewhere. And booze. Lots of booze.

There's plenty of humor as well, as evidenced in the sayings that the locals like to toss around such as "come on vacation, leave on probation." That popped into my head when I was pulled over by the cops my very first night in town. Apparently the headlight on my rented moped wasn’t functional. Who knew? I'm just a simple city boy from New York honey; "biker chick" is not yet on my resume. Another big one is "What happens in Key West, never happened." Take that, Las Vegas! Good thing too, because people here, primarily tourists, really carry on.

There are a number of clothing-optional resorts (men- only, women-only, as well as gay male and lesbian mixed); big events throughout the year encourage visitors to let go of their inhibitions, including the very popular Tropical Heat (August) and Fantasy Fest (late October/early November). But any night of the year can be a walk on the wild side, as Key West has an abundance of bars, clubs and saloons, offering everything from drag shows to leathermen to sweat-soaked partiers on the dance floor.

Oh, did I mention the alcohol? Key West is one of the booziest vacation spots I have ever seen; it’s like Provincetown with palm trees – and more cocktails. Seriously, this is a heavy-drinking town. It’s not hurricanes they should be afraid of, but lightning strikes—the whole town is flammable!

OK, maybe I'm overstating it, but like any tourist mecca, with all the happy hours, cocktail parties and binge-drinking-college-kids floating about, those struggling with a drinking problem may want to have their sponsor on speed dial. (There are of course many people in Key West living sober lifestyles, and there are a number of recovery resources in town, including Gay Alcoholics Anonymous at the Gay and Lesbian Community Center).

But I digress... There are so many wonderful reasons to come to Key West, such as... I noticed right away that there is a definite shortage of children on the island. Yes! It's not that I don't like kids, it's just that when there are young people in my vicinity, I just look that much older. Plus, kids suck up a lot of oxygen. So while I'm sure there were some brats, oops I mean children in Key West, I really didn't see any.

If you're an entertainment buff, the island has a lot of interesting sights including Tennessee Williams' former home; and the movie based on his play The Rose Tattoo was filmed in Key West. Other notable residents (both full time and seasonal) have included Ernest Hemingway (check out the Ernest Hemingway Home and Museum and its resident multi-toed cats), Calvin Klein and Jimmy Buffet. Recently out actress Kelly McGillis has been a familiar face in town and once owned a local (and still popular) restaurant called Kelly's.

For the active traveler, there is much to do, most of it based on the water (Key West is nestled in between the Gulf of Mexico and the Atlantic Ocean). Snorkeling, kayaking, jet skiing, sailing, swimming; if you're into water sports (and you know you are, Mary), there's plenty of it! Para-sailing and dolphin safaris are also available for thrill seekers.

Getting around town is a snap, even for a dizzy queen like me. The island is only seven square miles total, and once you figure out which body of water is which, you're home free. Bikes and mopeds are available for rental, and every place seems to be only a three-minute drive to everyplace else.

One thing I found charming about Key West were all the wild chickens roaming around. They are everywhere! Apparently they are descendants of birds that Cuban immigrants had brought over for cockfighting. (Boo! Hiss!) Some locals love them for their bug-eating services, others not so much, due to their crowing, which is loud and not exactly timed to the rising of the sun. There is a rumor floating about the climate keeps their testicles too warm, and throws off their natural crowing schedule. That may also explain half the action on Duval Street.

The local Key West crowd is a warm, welcoming and funny lot. A friendly bunch they are, with some colorful sayings and practices, including a whole unofficial residency system involving "conchs." (Key West is also known as "The Conch Republic," having briefly, in tongue-in-cheek fashion, seceded from the United States in 1982.) If you're a Key West native, you're a "Saltwater Conch," and non-natives are known as "Freshwater Conchs." Remember dear, these folks do spend a lot of time in the sun.

Another phrase the locals toss around is "Sister Season." This refers to the months of August and September, when tourism usually dips. With fewer out-of-towners to have fun with, the locals turn to their nearest and dearest for… affection. Picture a lot of donut bumping, or carnal cannibalism if you will. It reminds me what my wise old granny used to tell me when I was growing up: "Remember Bubala, two bottoms don't make a top."

With its tropical climate, lush plants and flowers and easy, breezy, beautiful way of life, Key West is rightly considered by some to be paradise. While there's more of a straight presence than in its homo heyday of the 1970s and '80s, the island is still an amazingly welcoming place for LGBT tourists and residents alike. Key West had the first openly gay mayor in the country, way back in 1982, and today, the chief of police is out and proud (and hot!) Donald J. Lee, Jr.

So whether you are the lay-by-the-pool, sip-cocktails- and-boy-watch type, or a scuba diving fanatic, or in the mood for some fierce and fun drag entertainment, Key West remains a unique and fabulous destination. As The Village People proclaimed in their popular disco ode to the town, "I'm headin' for Key West, the key to happiness!"

Alexander’s Guesthouse

The charming Alexander's Guesthouse is located on a nice quiet street in Old Town, and is one of the island’s best places to stay. Alexander's welcomes both gay men and lesbians, and is clothing optional in certain areas, such as the multiple sundecks. The landscaping is generous, well chosen and lush; the "three tropical B's" ( bamboo, banana and bougainvillea) feature prominently.

Socializing takes place around the lovely heated pool, bubbling spa, and at the poolside bar where cocktails are served from afternoon into evening. The rooms themselves are minimalist in décor, comfortable and immaculately clean. Add to that the friendly, unobtrusive service and overall feeling of tranquility and Alexander's is a top choice. Perfect for couples on a romantic holiday, business travelers, and those who prefer relaxed environments. Luxe and lovely, sexy with out being sleazy.

Island House

If sleaze is what you're after, (and there’s nothing wrong with that!) you should certainly check out the Island House. This very clothing-optional men’s resort is essentially a bath house with sleeping quarters and a restaurant attached. If you’re looking for sex, you will find it here.

Cruising takes place on every square inch of the property; at the café and bar, in the large swimming pool and popular Jacuzzi, and probably in the housekeeper’s supply closet as well. Upstairs is a dim and mazelike "cultural center" (one hopes the culture is penicillin); there is a health club on site for those who simply must work out even on vacation. Day passes are available.

Azur

I am a hungry hungry hippo, and despite the hot Florida sun, my appetite in Key West was in still high gear. Luckily for me, and no so luckily for my love handles, there was plenty of delicious food to be had. Among my favorite Key West eateries was Azur. Owners Drew Wenzel and Michael Mosi have created a charming and palate pleasing restaurant situated in the heart of the Old Town neighborhood.

Azur's menu has several delicious offerings, with a strong Mediterranean influence. Start with the warm Boucherondin goat cheese over baby arugula with walnuts, shallots and rosemary infused honey- divine! I savored every bite of the pan-seared chicken breast, which was served over broccoli rabe, Israeli cous-cous, artichokes and roasted red peppers in a roasted garlic broth. Delicious! Dessert was a lavender infused (wow!!!) crème brulee with fresh, sweet berries. I waddled back to my moped thoroughly satisfied!

Coffee Plantation

Coffee Plantation is a charming internet café located on a relatively quiet side street in Key West’s Historic Sea Port community. I popped in one day for a quick cup of java, and ended up staying for the afternoon. The coffee was tasty, as was the huge portion of fresh chicken salad on a toasted croissant I enjoyed.

Coffee Plantation also displays and sells some amazing pieces by local artists, as well as welcoming singers, poets musicians and others to come share their craft. They sell a line of very soft Coffee Plantation cotton tees shirts, and of course delicious java and tasty pastries. The vibe is chill and friendly, stop in when you’re in town.

El Siboney Cuban Restaurant

El Siboney Cuban Restaurant has been a Key West favorite since the mid-80's, and while I personally did not find the atmosphere to be relaxing, the food was outstanding.

This is classic Cuban fare: Enchilado de Camarón (Shrimp Enchilado), Costillas a la plancha (Grilled Pork Chops), and Paella Valenciana, offered with Plantanos Maduros, Yuca, Tostones and/or rice and beans.

El Siboney attracts a nice mixture of locals and tourists, but honey this place is loud; one has to shout to speak to one’s dinner companion. Also, my waitress kept screaming in my ear, and mainly in Spanish. But the food was flawless, the prices reasonable, the portions were huge and overall it felt like having dinner at the home of crazy but lovable relatives.

Bourbon Street Pub & Saloon 1 Bar

There’s also plenty of man meat to be had in this hedonistic tropical paradise; the Bourbon Street Pub features a nightly all Male Revue at 10 PM, a Best Ass Contest on Fridays, and a swimming pool full of hot boys. In the back is the Saloon 1 Bar which caters to the Levi/Leather crowd.

Kwest

Known as “the most changeable bar in Key West,” Kwest features jazz and piano music by day, but at night, the boys take over. The shutters close, and the crowd enjoys hot bartenders, male lap dancers and an amateur strip contest.

Bobby's Monkey Bar

A favorite hangout with local dudes, Bobby's Monkey Bar features karaoke nights, a pool tournament, and even a Wii for some video game frivolity.

Drag Galore!

And the queens... You’ll find some spellbinding attractions in the “Pink Triangle” section of Duval Street. Here is where the Key West drag community reigns supreme, wowing the crowds at the 801 Cabaret, Aqua and The Cabaret at La Te Da. These gals do it all: Dancing, live singing, lip synch, impersonation, dancing, comedy, outrageous costumes... Even drag queen bingo!

Key West is a true drag mecca, and boasts an impressive lineup of glittery talent, including Sushi, Randy Roberts, Gugi Gomez, Maya Montana and so many more. These bitches work hard for the money and look great doing it!

Blu Q Sailing Adventures

There’s much to do in Key West, and my highest recommendation goes out to Blu Q Sailing Adventures. Headed by friendly Captain Steve, a handsome and able mariner, Blu Q offers a variety of sail, snorkel, and cruise adventures for the gay traveler.

Not to be missed is the Island Time All-Male Sunset Sail. This two-hour excursion is a laid back and fun experience, as Capt. Steve chases the setting sun in the Gulf of Mexico. The sunsets are usually quite spectacular. On hand is shirtless sexy first mate Moe to serve up beer, wine, sangria and soft drinks. It's a sexy “light party” atmosphere; there’s music playing, the dudes on board usually strip down to swim trunks (or less) and a good time is had by all.

Another Blu Q trip I enjoyed was the gay three-hour Sail ’n’ Snorkel. Capt Steve sailed us out a few miles from the island and along with about two dozen other half-nekkid men, I slipped into the warm delicious waters. We saw a lovely assortment of tropical fish and large coral formations (Key West has the third largest living coral reef in the world) as well as some gorgeous but treacherous jellyfish (pretty things usually are quite treacherous). Our second stop was at Womany Key, part of the Key West National Wildlife Refuge. We weren’t allowed to go ashore as it was turtle-nesting season, but I snorkeled in the shallows, and was hypnotized by what I saw. I swam through hundreds of foot high sea anemones that resembled a forest of fluffy green lollipops, and got up close and personal with various undersea creatures (corals?) that looked like human brains, ribbon candy, and frosted Christmas trees. There were tiny white sea spiders lurking in the turtle grass, and an abundance of Queen Conchs.

Truly I could spend every day for the rest of my life snorkeling in that water! I surfaced just in time to hear first mate Moe advising the naked men in our group to ‘'keep your goodies below the water line'’

Key West Butterfly & Nature Conservatory

Back on dry land, I had a wonderful visit to the Key West Butterfly & Nature Conservatory. Visitors are welcomed by a 15-minute film which describes the life cycle and basic facts of interest about butterflies, but the real magic happens in the Conservatory. The moment one steps into this warm and humid enclosure, the real world just melts away; there are butterflies everywhere, flitting around, dancing in the air as butterflies are known to do, and just generally making a dazzling spectacle of themselves.

The conservatory is well landscaped with a variety of plants whose beautiful flowers provide nectar for the winged inhabitants. There are also plates of fruit placed throughout (for the lazier butterflies?) which also provides some nice up close photo opportunities of these "flowers of the skies." Among the 50-60 species present, my personal favorite was the "Blue Mopho"; they were quite large, and seemed to roam the space in packs, showing off their iridescent blue wings with a distinct "Look at me, I'm beautiful dammit!" attitude. And they truly were!

Jazz in the Garden

Music lovers flock to the The Gardens Hotel for "Jazz in The Garden" every Sunday from 5:30-8 PM, for an evening of wonderful live music, cocktails and socializing. The Hotel is one of the finest places to stay in all of Key West, with classic Bahamian architecture, 17 beautifully appointed rooms, an aviary (!) and some truly spectacular landscaping (From 1930- 1968, the estate was The Peggy Mills Botanical Gardens). Gorgeous.

Fort Zachary Taylor Historic State Park

One last spot I would like to suggest is the beach at Fort Zachary Taylor Historic State Park. Known by the gays as “Liz Taylor Beach” it’s peaceful and easily accessible; be warned though that this isn’t a soft sandy beach. Sharp coral fragments line most of the shoreline, and while there are patches of gentle sand, if you go into the water (warm and lovely) wear swim shoes to protect your footsies. There are also some lovely Australian pines, picnic tables, a concession stand and a nature trail. A wonderful way to spend a balmy Key West afternoon.

Fantasy Fest

Among the special events that take place in Key West throughout the year, the biggest is Fantasy Fest, held every October. Fantasy fest is a totally fabulous, week-long, non-stop party, filled with outrageous costumes, body painting, a pet masquerade & parade, countless crazy house parties, fetish balls, a parade, the Coronation of a King & Queen (the reigning champs are King Ralph & Queen Vicki) and the fantastical Headdress Ball. The Fest is also a huge fundraiser for local AIDS charities, including AIDS Help.

Bone Island "Bare It All" Weekends

June and December see the sizzling "Bone Island Bare It All Weekends" and as the name suggests it is a wild celebration of exposed flesh. Key West welcomes hundreds of naturists, guys who like to get naked, and those who like to watch. Scheduled events include foam parties, pool parties, dance parties (lots of parties!) all sans clothing. There is even a naked shopping trip at Graffitti Menswear for those who seek a little in the buff retail therapy.

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