Key West is the reward – as if you needed one – for taking the road all the way south.

By Thomas  Swick

LIVING IN SOUTH FLORIDA AT A TIME of backyard travel is a bit like being Bernie Madoff under house arrest. Yes, you’re limited in your movements, but what riches there are within easy reach.

Those of us fortunate enough to make our homes here can hop in the car and head in three directions. (Amazingly, some local drivers manage to do this simultaneously.) To the north are the playgrounds of Daytona Beach and Orlando; to the west the islands of Marco, Sanibel, Captiva, Gasparilla. To the south we’ve got the trifecta of Miami, the Everglades, and the Elysian Keys. And those are just the highlights. Your head turns, 180 degrees, with possibilities.

When mine came to a stop, it was looking southwest, so I got in the car and pointed it towards Key West. The world could be going to pieces and the road through the Keys would still lift the spirits. Because these islands seem far removed from the world, connected to it, tenuously, by bridges that are less like the Golden Gate than like low-flying carpets. Driving, you enter a kind of trance – carried by wind, saturated by sky, grazing the water. More than a feeling of vacation, going to the Keys gives you the sensation of escape.

The names – Key Largo, Islamorada – are rich with associations and intimations of fable. You pass marinas, shell shops, fish houses, schools – which always surprise. Shouldn’t these kids be out playing with Flipper? Water is your constant companion, glimpsed at the end of short-lived streets; even when you can’t see it, you know it’s there. You’re not just driving anymore, you’re rock-hopping an archipelago.

Key West is its endpoint and apotheosis. Deposited onto Truman Street, you are quickly immersed in whitewash and lushness: two-story houses belted by fences and shaded by gardens. There is an old-fashioned feel to the place – alleys, porches, people on bikes – that reminds you of visits to your grandma’s in smalltown Pennsylvania (or Vermont or Kansas). It is your reward, as if you needed one, after the beauty of the road.

The rap against Key West is that it’s not what it once was. And you’re never quite sure which lost civilization the whiners are pining for. Is it the bustling port of the mid 1800s, the richest city per capita in the southern United States? Is it the newly poor and literary town of the 1930s: bodegas, cock fights and Hemingway sightings? Is it the slacker capital of the ’70s, with its frozen and soon-to-be-trademarked concoctions? Is it the serio-comic Conch Republic – “We seceded where others failed” – of the ’80s?

Since then Key West has become a home to gays and a workplace for Eastern Europeans, continually evolving as all cities that don’t flat out stagnate must do. The glory of the place is that traces of all its incarnations can still be found, if you know where to look for them. And while you’re looking, you’ll eat finer and sleep better than Hemingway did.

The Casa Marina still lords over the southern shore. Built in 1920, and on the National Register of Historic Places, the hotel offers rooms with not only air conditioning but wireless Internet access. (Papa would surely have approved of the latter; summer visitors will appreciate the former.)

A few blocks away, in this more peaceful end of the island, sits Louie’s Backyard, a two-story pink house that serves excellent food in quietly elegant rooms as well as on a deck overlooking the ocean. Joy Williams, in her classic guide The Florida Keys, writes of the pleasures of dining at Louie’s under the stars.

Around another corner you’ll find Santa Maria Suites, a former motel with MiMo touches that has been turned into a spiffy boutique hotel. It houses what must be the most visually stunning restaurant on the island. Ambrosia is shaped like a bow tie with a sushi bar at one end and a sake bar at the other, a glass-walled waterfall peacefully cascading at the knot. Feng shui meets the Jetsons.

The famous Conch Train winds through this neighborhood so you know it’s important. The beach may be small, but it was good enough for Tennessee Williams, who swam at it every morning. “I work everywhere,” a sign in the sand quotes him as saying, “but I work best here.”

Southernmost House, a 19th century residence turned 20th century nightclub, is now a turreted 13-room hotel. The door knobs seem ridiculously low until you realize the panes of glass are purposefully long to better capture the view of ocean and sky.

Here Duval Street is more art-lined than T-shirted. The Hands On Gallery specializes in hand-woven silk and linen clothing as well as contemporary jewelry; Gingerbread Square Gallery showcases paintings, art glass and sculptures; South Pointe Gallery sells original poster art, gloved staff carefully lifting each period illustration from one pile to another for nostalgia-seeking customers.

A few of the stores occupy old conch houses not far from the Adult Entertainment Club. On its porch one evening – here even the sex industry comes with porches – a young woman sat reading Irène Némirovsky’s Suite Française.

Working your way down Duval, you pass the piano bar Keys; the bistro and wine bar nine one five (a delicious, contemporary chipotle conch chowder), the San Carlos Institute (the Cuban heritage center). T-shirt shops begin to kick in – infuriating purists while single-handedly (or chestedly) keeping alive the art of the anonymous epigrammist. These are soon followed by bars with live bands. “Welcome to south of the real world,” Terry Cassidy shouted from the stage of Sloppy Joe’s early one weekday afternoon. Then he sang of the easy life in the Florida Keys.

The side streets hold more vestiges of the past: Bahama Village, Blue Heaven (al fresco dining under a Spanish lime tree), The Gardens Hotel, which features live jazz every Sunday at 5. The property was owned by Peggy Mills, a prominent woman of town, and her garden was an early tourist attraction. Today people coming to hear music can see the updated version created by current owner and art lover Kate Miano. There is a sculpture of a crane sitting on a bench and reading a book (this has to be the best-read town in Florida); nearby a cherub rides an ostrich. There’s a cat burial ground, a small pond that Hemingway supposedly fell into, enormous earthenware pots from Cuba and two resident tortoises, Thelma and Louise.

On the other side of Duval sits the Truman Little White House and you don’t have to take the tour to learn that the president, while in residence, held “loud shirt contests.” This bit of trivia is found under a picture in the free and informative exhibit next to the gift shop, which sells T-shirts (inevitably) proclaiming “Friends don’t let friends vote Republican.” (Or, if you prefer, Democrat.)

The Museum of Art & History at the Custom House possesses a fine collection of colorful wood paintings by local folk artist Mario Sanchez. Here the vanished world of cigar factories and card games is preserved.

From the museum it’s a short walk out to Mallory Square. The sunset buskers have increased in number over the years, including in their ranks “The Southernmost Bagpiper,” a Polish journalist moonlighting as a fortune teller, and a female fire breather. It is a gloriously eclectic gathering, and as you stroll from act to act, the hennaed disc about to take its celebrated dive, you realize with a pang that you have to leave tomorrow. Then, to console yourself, you think of the resplendent drive back to reality.

*If You Go

Getting There

Take Florida’s Turnpike south until it runs into Route 1. Continue south on Route 1 as far as it goes.

Lodging

For the quintessential Key West experience – sleeping in a gracious white house set in a verdant garden, it’s hard to beat The Gardens Hotel, 526 Angela St., 305-294-2661, gardenshotel.com. If you don’t stay here, at least come for the jazz at 5 p.m. on Sunday (though check for times, as the musicians take a break during some of the summer months).

Casa Marina Resort & Beach Club is sort of The Breakers of Key West, with something not easy to find on the island: a beach. 1500 Reynolds St., 305-296-3535, casamarinaresort.com.

Santa Maria Suites, 1401 Simonton St., 866-726-8259, santamariasuites.com.

Southernmost House, 1400 Duval St., 866-764-6633, southernmosthouse.com.

Eating

Louie’s Backyard, 700 Waddell Ave., 305-294-1061, louiesbackyard.com.

Nine One Five: Bistro And Wine Bar, 915 Duval St., 305-296-0669, 915duval.com.

Ambrosia, 1401 Simonton St., 305-293-0304.

Blue Heaven, 729 Thomas St., 305-296-8666.

Sights

Museum of Art & History at the Custom House, 281 Front St., 305-295-6616, kwahs.com/customhouse.htm.

Truman Little White House, 111 Front St., 305-294-9911, trumanlittlewhitehouse.com.

The Ernest Hemingway Home & Museum, 907 Whitehead St., hemingwayhome.com. (Open 365 days a year, 9 a.m. to 5 p.m.)

Mallory Square, at the northern end of Duval St.