I like Key West because it is replete with characters, and often weird juxtapositions of these people, usually when you least expect it. I lived there for five years in the 1990s, but when I go back, I am still surprised by new faces and stories. There's the five-condo owning author who tends bar twice a week "because I like to meet people," the maintenance manager of a museum asking me to help him find a biography of Marcel Proust, and the airport baggage handler who writes like a Dave Barry (or Proust, come to think of it again). Then there's the local politician who organized his own "same-sex straight wedding" a while ago and the distinguished minister who dresses beautifully in bright red jacket and trousers on occasion. Another character is Jim DeKeyrel, who owns the Crazy Boat (, which is guaranteed to get you wet on your ride through local waters. At time of writing, you can only book him if you arrive on a cruise ship, but there are plans afoot to let landlubbers take the trip in the near future. But I have to stop, having met too many unusual characters on this last visit alone.

In addition to the activities for which Key West is famous (mostly watery and outdoors) and its high season cultural events (symphony, theater, literary lectures, etc.), this end-of-the-country venue is a great place to dine out. From humble piles of wood (real shacks) such as BO's Fish Wagon, which also resembles a large car wreck, to elegant waterfront properties like Louie's Back Yard, there are at least 285 places (in a town with only 24,000 permanent residents) where you can get a good meal, and a few of those are simply great.

Dining Out

Kelly's is Key West's most appealing restaurant in my opinion, in equal parts because of its ambiance, its food and its historic resonance. Located in the old house where Pan American World Airways was born back in 1927, the restaurant is named for film actress Kelly McGillis and is a favorite hangout of the young, beautiful and restless. Kelly's ex-husband Fred Tillman and his wife, Sheila, now manage the place efficiently and yet with laid back Keys humor. (Evidence for the latter -- a burlesque show upstairs on Friday nights.) Most seating is open, but you can also eat at the indoor Pan Am Bar. I enjoyed their light crab cakes (Chesapeake-style, with mango salsa) at $19.95 and classic, spicy Conch Fritters ($6.95), but there is plenty of fresh fish on hand, including delicious grilled mahi-mahi ($19.95). Kelly's Caribbean Bar, Grill & Brewery, 301 Whitehead Street, Key West FL 33040, tel. 305/293-8484, website

I love Square One because it's sophisticated and laid back, simultaneously. The affable owner, Michael Stewart, is there to greet you most of the time, and lead you outdoors on the patio or inside to a more elegant ambiance. The food is proudly American, the piano music unobtrusive, the chatter at the bar pleasant and subdued in the background. High on my list of favorite appetizers is baked garlic, and a special entrée treat is the Triple Crab (Alaskan, stone and blue). Breakfast, lunch and dinner. Square One, 1075 Duval Street at Duval Square, Key West FL 303040, tel. 305/296-4300, website

One of my favorite lunch spots is Nicola Seafood at the Hyatt, where you can sit on the verandah overlooking the water, and enjoy the attention of a superb staff (waiter Nancy, especially). I had a moist Cuban Panini ($11.50), a sophisticated version of the traditional Cuban sandwich (pork, ham, cheese, pickles, mustard), with an herb spread. My dining companion had the Traditional Cobb Salad at $12, saying "I order this a lot here." Nicola Seafood, Hyatt Hotel, 601 Front Street, Key West FL 33040, tel. 305/809-1234, website

At La Trattoria, going strong since 1984, I enjoyed the aromatic vegetarian Spaghetti Norma ($16) and a local author who invited me let me taste some of her smooth Cannelloni della Casa ($15). We talked about her latest book while sharing a rich mousse au chocolat under the watchful eye of expert waiter Mark Fisher (no relation). La Trattoria, 524 Duval Street, Key West FL 33040, tel. 305/296-1075, website

Sushi-lovers should head for Ambrosia in its new location in the Santa Maria Hotel and they will find the best fresh fish in town, with a few cooked dishes (tempura, etc.) on the menu also popular. Ask Noriko for her suggestions. A moderate amount of sushi sampling should run about $35. Ambrosia, 1401 Simonton Street, Key West FL 33040, tel. 305/293-0304, no website.

You can have drinks up on the new Tower at the Turtle Kraals restaurant while you watch the sun set across the masts of boats in the Historic Harbor, then descend to good seafood specialties at moderate prices below. They are famous for their mango crab cakes ($15.95), which I enjoyed, though I would also recommend the jalapeno fritters ($6.95). Turtle Kraals, 231 Margaret Street, Key West FL 33040, tel. 305/294-2042, website

If you want to put together a picnic, you can visit the big supermarkets out in the New Town area (you'll need a car) or hoof it over to the Waterfront Market or Fausto's for your food and wine. Fausto's is closer to the center of town, but Waterfront has more variety in every way. Fausto's will deliver to your hotel except on Sundays. Fausto's, 522 Fleming Street, Key West FL 33040, tel. 305/296-5663,

The Waterfront Market, right on the historic harbor, is threatened with closure by developers, but if it is still open, you can find a huge variety of cheese, wine and deli items here. Waterfront Market, 201 William Street, Key West FL 33040, tel. 305/296-0778, no website.


I have only one Margarita a year (well, this year it was two), so I'm no expert, but I have to declare a tie between my old favorite, Rooftops, and my new find, the bar at the Gardens Hotel. At Rooftops, you can drink under the huge tree that bisects its upper patio, looking out over Front Street and its relative hustle-bustle. At The Gardens, you are wrapped in a cocoon of quiet beauty and idle chitchat, so take your pick. Rooftops Café, 308 Front Street, Key West FL 33040, tel. 305/294-2042, no website. The Gardens (see Lodging, below).

Of course, if you're celebrity-mad, check out Jimmy Buffett's Margaritaville, where you may even see the songster from time to time (he lives here part of the year.) Margaritaville Café, 500 Duval Street, Key West FL 33040, tel. 305/292-1435, no website.


With a plethora of hotels, the high season notwithstanding, there were plenty of Vacancy signs around town when I visited in late January. Each year when I visit, I look for a place where I would love to stay were I not sleeping in a museum's guesthouse for writers in residence. This year, the winner of my informal award is The Gardens Hotel, a surefire bet for luxury lovers who also want personal attention and a great location in the heart of Old Town. The former home of an eccentric garden-lover, Peggy Mills, the hotel has only 17 suites and rooms, mostly in modern annexes arranged around a shaded pool and yes, surrounded by gardens on what was once the island's largest private estate. If you don't stay here, consider coming on Saturdays for their Jazz Evenings, when a three-man group plays elegantly, never noisily, for contented listeners in the pool area. Rated best in town by Zagat and on several other "best places" lists. Owner (since 2004) Kate Miano seems to be on scene constantly, a good sign.

Room prices start at $300 in the high season (Dec. 22 to May 26), and are cheapest (from $160) in low season (Aug. 16 through Sept. 30), with minimum stays during certain holiday periods. The Gardens Hotel, 526 Angela Street, Key West FL 33040, tel. 800/526-2664 or 305/294-2661, website


The official website for Key West is, and that takes in all the Keys, too. Two very helpful commercial sites: and, both crammed with information. Frommer's publishes Frommer's South Florida, which includes coverage of the Keys.

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