Key West is a curious confluence of history and hubris, sleaze and sophistication, literature and licentiousness. A two-by-four-mile sliver, it's big enough to contain poets, painters, crooked politicians, cigar makers, lawyers, transvestites, and the owners of far too many T-shirt shops. While this reliance on tourism constantly threatens to destroy a place that has survived it all, from hurricanes to the AIDS epidemic, nothing can stop—or whitewash—the legendary kookiness. I recently popped in to see a psychic there. She said I needed rest and that the spirits told her I do something both creative and stressful for a living—writing, she declared. "What do you write, honey?" she asked. "Fiction or un-fiction?" Therein lies the definition of the real Key West: it's both fiction and un-fiction.
Where to Eat
There's no point in traveling to the only place in America that never has frost if you don't spend as much time as possible outdoors.
Alice's on Duval 1114 Duval St.; 305/292-4888; dinner for two $65. This restaurant is not technically outdoors, but it sure feels that way. It has windows all around, suggesting the Key West of 50 years ago. Balmy breezes complement the wonderful food. Be on the lookout for Alice—you can't miss her. Try the spicy pink-vodka conch chowder, the papaya-marinated skirt steak, and the macadamia-coconut-crusted shrimp.
Blue Heaven 729 Thomas St.; 305/296-8666; breakfast for two $20. Although it also serves lunch and dinner, come for Breakfast with the Roosters. While eating fresh fruit and banana bread or seafood Benedict, you'll find Easter-perfect chicks and their nervous parents chirping underfoot in the dirt yard.
Casablanca Café American 904 Duval St.; 305/292-2300; dinner for two $50. It's fairly new in a town known for here-today-gone-tomorrow, but the buzz is that Casablanca's going to make it. Start with hand-rolled Key West Havanas (smoked chicken, chorizo, black olives, and jack cheese in a pastry leaf served with a burnt orange-mango barbecue sauce), then have sautéed yellowtail snapper with shaved fennel salad and artichoke-and-black-olive salsa cruda.
Latitudes Beach Café Sunset Key; 305/292-4313; lunch for two $40. The restaurant at Sunset Key Guest Cottages is open to the public, as is the beach ($20 for an all-day pass). There is a brand-new pool bar called Flippers, and waiters will even serve you lunch while you sunbathe. The launch from Key West takes just 10 minutes, but you have to reserve a seat. Try the guava-glazed chicken breast sandwich.
Louie's Backyard 700 Waddell Ave.; 305/294-1061; lunch for two $40. Facing the Atlantic Ocean, this restaurant is in a gorgeous, pale-pink restored house, with deck dining beneath two huge mahoe (also called Florida hibiscus) trees. It may well be the town's best-known and most popular restaurant. Order the seared sea scallops in a roasted-coconut-and-curry cream sauce, served over lobster linguine.
Mangoes 700 Duval St.; 305/292-4606; lunch for two $40. Celebrating Key West's Bahamian and Cuban influences, Mangoes' specialties include fritters stuffed with tender conch and vegetables, served with cocktail sauce and Key lime mustard. The restaurant's courtyard has nooks for romance and huge umbrellas to block both the sun and tropical rains. There's also an airy upstairs balcony overlooking tourist-trampled Duval Street, a good vantage spot for people-watching.
Going Indoors for
Antonia's 615 Duval St.; 305/294-6565; dinner for two $60. The locals and tourists who know Key West restaurants were dismayed in 1996 when a fire next door took Antonia's with it. It has reopened, and the exquisite northern Italian food is better than ever.
Café Marquesa 600 Fleming St.; 305/292-1244; dinner for two $75. This see-and-be-seen restaurant is gorgeous, with mahogany molding, stone floors, and bay windows. Take your pick: mango barbecue prawns with salsa verde and red bean relish, sesame-crusted tuna with miso rémoulade, or tequila- and lime-cured salmon tostada with habanero salsa, crème fraîche, and caviar.
Bring on the Night
Much of Key West's sense of fun comes from its gay residents, but there's no separatism—everyone's invited to this island party.
Atlantic Shores Resort 510 South St.; 305/ 296-2491. This low-slung Art Deco motel offers some of the best entertainment in town. Sunday night dances are a tradition in Key West, and Atlantic Shores has been hosting one for 15 years. It begins poolside at 8 p.m. and extends along the 150-foot pier jutting into the Atlantic. A DJ plays manic house music and people dance under the stars. Thursday night brings Atlantic Shores' extremely popular Cinema Shores. The parking lot is transformed into an outdoor theater with free popcorn and servers peddling drinks to patrons reclining on chaise longues. Children (depending on the movie) and dogs (always) are welcome, and there are door prizes, including certificates for facials and dinners. The movies begin at 8 p.m. and cost $3. (Daytime visitors to the motel pool—you can rent a chaise and a towel for $3—should know that it's the only public "clothing-optional" pool in town.)
801 Cabaret 801 Duval St.; 305/294-4737. The best of many Duval Street nightclubs—Bourbon Street Bar, Diva's, and Epoch are others—that offer cabaret shows starring drag queens. A few of them manage to make Lady Chablis of Midnight in the Garden of Good and Evil fame seem downright frumpish. For something even more unusual, stop by Sunday from 4 p.m. to 7 p.m. for a frothy frozen drink and a spot of bingo. The caller is a comedian dressed as a nun.
For over a quarter of a century, artist and self-described "old hippie" Nancy Forrester has cultivated her back yard into a jungle of palms and succulents, a collection so breathtaking that Charles Kuralt rhapsodized over the garden in his last book. A few years ago, she opened it to the public, calling it Nancy Forrester's Secret Garden (1 Free School Lane, no cars; 305/ 294-0015; $6 admission). Forrester and her longtime companion, Elliott Wright, nurture more than 150 species of palms, including specimens from the Pacific Marquesas Islands and the Seychelles, and near-extinct ones from Cuba's Pinar del Río and Oriente provinces. The garden is also lush with bromeliads, orchids, arums, ferns, and bog plants—it's an antidote to a somewhat overdeveloped island.
The Monroe County May Hill Russell Library (700 Fleming St.; 305/292-3595) has a lovely oasis, thanks to a gift of more than $100,000 from a wealthy benefactor. (Word has it he was murdered by his lover—the librarians can provide the details.) He gave the money to be used for a palm garden; the result is both lovely and free. You might see Annie Dillard wandering around, or Alison Lurie, Ann Beattie, or any of the other writers who live either full- or part-time on the island.
Yes, Sunset Celebration at Mallory Square is hokey and taxing. Locals would never, of course, but that doesn't exempt you. Arrive 30 minutes before sunset: nature's show is magnificent, but the real draw is the manic backup performances from an array of sword swallowers, contortionists, and tightrope walkers. For such a touristy spectacle, you'll be shocked at how much attitude gets thrown around. For example, there's the Hungarian circus performer who lifts heavy objects—with his mouth—such as a car tire or a chair, but not before asking daringly, "Do you give a daahmn?" Or even better, the unicyclist with a hoop-jumping Vietnamese pig; he taunts bratty children with remarks like, "Tell your mom it wasn't really a good idea to drink while she was pregnant with you."
Old Old Town
Bahama Village, the historic Afro-Caribbean section of Old Town, is much as it was five generations ago when black and white Bahamians and Cubans settled on this island. Their descendants still live in tiny shotgun cottages. The area is filled with small markets, bakeries, barbershops, rib shacks. Lots of friendly dogs and barn animals roam the streets. "The fact that it hasn't been lost—that paint-peeling, Tennessee Williams— esque, living, breathing community—is amazing," says tour guide Sharon Wells. "It represents a Key West that is rapidly disappearing." You can enter at Petronia and Duval, where an elaborate wrought-iron archway heralds the neighborhood. Bahama Village is bordered by Angela, Duval, and Louisa Streets.
The Right Guides
The island isn't big, but with so many layers of history, it helps to have a guide. Exactly which kind of guide you want is up to you.
About six years ago, Lloyd Mager was doing odd jobs (the way many people support themselves on this island if they lack that trusty trust fund) when he decided to transform his passion for the place and his hatred for development into a career. Of sorts. Mager runs the extremely unstructured Lloyd's Original Key West Nature Bike Tours ($15; 305/294-1882).
While Key West is mellow, Mager, born in the Bronx and reared in New Jersey, is not. It is immediately clear that he was once an inveterate horn-blower who gave inappropriate finger and hand signals to anything that stood in his way. As a tour guide, he is all coiled energy, a machete-brandishing hellion on wheels. He uses the tool to hack open coconuts, which he carries in his bike basket. (He also carries Key West limes, cutting them open and squeezing the juice into the coconut. His followers get to gulp the irresistible combination, accompanied by his off-key version of "You put de lime in de coconut…") Making his way into people's yards, he plucks and serves up all manner of fruit—mangoes, star fruit, sapodillas. Too much traffic, overdevelopment, or a recent ordinance that keeps him out of the historic cemetery (no bikes allowed) can send Mager into a rant while he's riding, but he's a nice man, really. He occasionally makes a mistake when describing architecture or island history, but he never errs with plants, trees, or Key West's gloriously aromatic flowers, including gardenia, frangipani, and jasmine. He will hold a blossom to your nose and order you to sniff. Don't refuse. The man has a machete.