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An Insider’s Guide to Key West

Some people who moved to Key West because of its funky, sea-beaten patina aren’t as impressed by the sudden spurt of beautification as visitors are. But we promise it’s a good thing.
By Wick Allison |

Key West has been flooded before, but this time it’s with cash. A giant wave of investment has doubled the prices of its quaint old Victorian homes and inspired some of America’s toniest retailers to open shop. For the town, this isn’t necessarily good news. For the visitor, it isn’t necessarily bad news.

Locals aren’t happy. Costs are up, and so are taxes. As a result, Key West is suddenly spruced up. The streets have been repaved, the parks replanted, the buildings painted. The town looks good. In fact, it looks better than I’ve ever seen it, and I’ve been an annual visitor, and a sometime homeowner, for nearly 30 years.

But people who came to live in Key West because of its funky, sea-beaten patina aren’t as impressed by this sudden spurt of beautification as visitors are. “Is Key West really supposed to look good?” one longtimer asked me.

The same point was raised by an old friend, a novelist who has lived in Key West off and on for two decades. A flood of money raises prices, and when prices start soaring, developers start building. Evidence of a speculative boom is everywhere. The noise of carpenters sawing and hammering is now more common than the call of sea gulls. On a walk around town, my friend pointed out with amusement a plain, two-story house on a tiny lot now on the market for $1.5 million. “All we need is one good hurricane,” he said.

Hurricanes have brought Key West low before. In the 1890s, it was the richest city per capita in the United States, with not a little of that income produced by old-fashioned pirating. After a hurricane struck, the town’s slow decline began. Another hurricane in the 1930s permanently severed the town’s rail link with the mainland, and Key West sank into poverty.

So this is a town accustomed to booms and busts. It is an island of fantasy, but also of tragedy, and the foretaste of sudden disaster lingers in the air like the sweet scent of rotting fruit.

History makes Key West an inviting place to wander around, either on foot or by bicycle. A lot of its history is hidden behind lush foliage and paint-peeled porches. Stop by Key West Light Gallery on Fleming Street at Simonton Street (one of 70 art galleries in town) and ask about the walking tours with local guides. Guided tram tours also are available, and while the expertise of the drivers is hit or miss, they give a good, if somewhat sanitized, introduction to the island’s past.

There are a few good things to know when traveling to Key West. The first is that the island is rock, and beaches are hard to come by. Smathers Beach, on the road in from the airport, is public and good. The private beach at the Wyndham Casa Marina Resort, built in 1921, is better, but it’s for guests only—and closely monitored. A smaller public beach behind the Dewey House, on South Street, is usually too crowded, except in the early mornings when the tai chi practitioners are doing their exercises.

The better restaurants require reservations during the season. There are easily 10 or more that reach the level of finer Dallas eateries, but two inexpensive ones, one Japanese and the other Chinese, are standouts. Kozuchi on Greene Street impressed my half-Japanese wife, and China Garden West on Fleming Street impressed the rest of us.

The trade winds make Key West pleasant any time of the year except September, when they inexplicably fall off. Even so, the temperatures never rise above 90 degrees. In the winter months, we always insist on a heated pool because the nights can cool down almost, but not quite, to sweater temperature.

American Airlines (800-433-7300. flies nonstop from DFW to Miami, with connecting flights to Key West.

If you want to rent a house, contact The Real Estate Company of Key West (305-296-0011. or Property Management of Key West (305-296-7744.

If a house seems like too much, you have another alternative. Many of the larger guesthouses have private cottages on their grounds. There are more than 80 inns in Key West, so it’s much easier to have a central reservations service do the work for you. For guidance on finding the right spot, call 877-243-2312. We recommend Wyndham Casa Marina Resort (1500 Reynolds St. 305-296-3535. and Hilton Key West Resort & Marina (245 Front St. 305-294-4000.

512 Greene St. 305-292-0009

China Garden West
531 Fleming St. 305-296-6177 

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

Sunset Celebration at Mallory Square

Waterfront Market
201 William St. 305-296-0778

Key West Light Gallery
534 Fleming St. 305-294-0566

Duval Street
On a stroll along this famous street you’ll find a large variety of Caribbean and local artwork, paintings, photography, sculptures, and handmade items such as hammocks and tie-dyed t-shirts.


Clowning Around Key West

Every night in Key West, as the sun starts its stunning, slow descent into the Gulf of Mexico, a fireworks show erupts on the water. And a festival breaks out on the land.

It’s the Sunset Celebration, a rite of passage for any tourist to the Southernmost City. Unicyclists, jugglers, illusionists, and contortionists begin loosely scripted shows along the waterfront courtyard of Mallory Square and the adjoining Hilton Hotel pier. Local craftsmen, selling everything from painted scrap metal to carved coconuts, crowd the courtyard.

“It’s really magical,’’ says Steven “Bounce the Clown’’ Margil, who was the first juggler to toss his clubs in the air at Mallory Square 30 years ago. Today, Bounce, his wife Karen (better known as Mademoiselle Ooh-La-La), their 13-year-old acrobat son Daniel, and their poodle Top Hat have long been sunset fixtures. When he first arrived, there was no celebration. Musicians, following the lead of Key West’s patron saint, Jimmy Buffett, occasionally played the square—at least whenever a local cop didn’t chase them away.

Bounce added juggling. Others followed, like Johnny, the acrobat from Guyana, and Patrick, the trick bike rider from Canada. Now, there are usually about 20 performers lined up along the waterfront, and much of the city’s tourism industry is geared around sunset.

“Every night the sunset is different,” Bounce says. “Every night the celebration is different. And so many people who come here have never seen a festival break out spontaneously. It’s a free event, and it’s just a great way to kick off the night in Key West.’’


How to Rent a House

Hotel rooms are for tourists. To get the real feel of old Key West, longtime visitors know a secret: rent a beautiful Victorian home to call your own.

Several good firms specialize in vacation rentals. I recommend The Real Estate Company of Key West or  Property Management of Key West, both of which I’ve depended on for years. For holidays, the sooner you call, the better, obviously, but for most of the year a range of options is open to you.

In choosing your house, the first thing to decide is how many bedrooms you’ll need. When talking to the agent for the first time, the key question to ask is, does it have a transient license? Key West, a semi-socialist state, recently restricted the number of houses for rent. Your agent’s job is to make sure that when you arrive, your house can be legally occupied. By asking that question, you are letting the agent know that you know a license is required and to skip any property that might cause a problem later on.

The next question is, what part of town? We prefer Old Town and the Truman Annex. Areas to avoid are New Town and The Meadows, not because there’s anything wrong with them, but you’re there to soak up the ambience, and they don’t have much.

Old Town is exactly that, the original seafaring town with many homes built by sea captains, scavengers, and privateers. Truman Annex is a relatively new development on the former Navy base the late president liked to visit. It is close to the center of town—so close that the bar noise can go late into the night—and the old officers’ homes are now private residences.

The great thing about a house is that you can cook your own meals, do your own laundry, and, in general, live by your own schedule. We are usually at the  Waterfront Market by 5 p.m., when the fishing boats come in, to pick up that night’s dinner. —W.A.