Key West, Florida

By Jane and Michael Stern

Originally Published 1997 Gourmet Magazine

In April 1982 citizens of Key West seceded from the Union. Their insurrection was provoked by the U.S. Border Patrol, which had started searching everyone who traveled between mainland Florida and the Keys. The blockade was abandoned, but the short-lived revolt confirmed a long-known fact: The nation’s southernmost city has a mind of its own. Calling themselves “Conchs” (pronounced “konks”), an old term for island natives, the mischievous rebels—whose missiles consisted of stale Cuban bread thrown into the air—declared their land the “Conch Republic.” 

Formally, Key West remains part of the United States, but for many who love it with patriotic zeal the Conch Republic is a virtual nation with an insouciant culture found no place else. 

For over a hundred miles into the blue-green waters of the Gulf of Mexico, Florida’s coral keys are threaded by a two-lane overseas highway that sweeps past fish camps, mangroves, glittering ocean views, and glaring roadside kitsch. At the end of the road is Key West, a two-by-four-mile island where the sky is always blue, and where iconoclasts and hedonists have always felt at home. “Welcome to paradise!” is a common greeting on the island, spoken without a hint of irony.

Paradise or not, you know for certain that Key West is different when you have breakfast at RICKY’S BLUE HEAVEN in the island’s old Bahama Village. It is Conch to the core—a helter-skelter haunt that has been the home of a boxing ring (Ernest Hemingway sparred here), a bordello (the tiny rooms upstairs are now part of an art gallery), and a cockfighting pit (heroic roosters are buried in a grave-yard behind the dining area), as well as the inspiration for islander Jimmy Buffett’s song “Blue Heaven Rendezvous.” Today, the sprawling indoor-outdoor restaurant shares space with artists’ studios, a one-dollar shower stall, a bakery, and a hemp shop. Three meals a day are served, but we like breakfast best because of the company: a rooster and a lively flock of hens who scratch about the dirt-floored patio among the tables, crowing and cackling at the morning sun and some nesting, with newborn chicks under their fluffy breasts. 

How sweet it is to fork up banana pancakes under the shade of an ancient banyan tree and while away a carefree morning alfresco. Orange juice is Florida-fresh; granola is perfume-sweet, available with cow’s milk or soy milk; coffee is served in miscellaneous souvenir mugs. Pleasant as breakfast is, don’t snub Blue Heaven supper—jerk chicken and barbecued shrimp are legendary, as is the flamed Banana Heaven dessert—and shrimp and grits at Sunday brunch are a delight; but any time other than early morning the wait for a table can be maddening (Blue Heaven takes no reservations). 

Sunrise is a good time to share a meal with Conchs while vacationers are still asleep, so we’ll dote on one more good breakfast place: PEPE’S, a personality-plus eatery that touts its status as Key West’s “eldest” (since 1909). 

“I could be you! You could be me!” exclaims our waitress with glee, setting down her ever-present pot of coffee to write an order that happens to precisely match what she likes to eat in the morning: an omelet of jack cheese, Anaheim chilies, and smoked sausage sided by a creamy griddle-cooked mashed potato patty and a slab of bread du jour—warm coconut bread nearly as sweet as cake. Later in the day, Apalachicola Bay oysters by the dozen—raw or baked—make Pepe’s a destination for rapacious appetites. Weekly traditions include a Sunday night barbecue and a full Thanksgiving dinner every Thursday. And who can resist a menu that offers both a blue-collar burger and a white-collar burger? (The former is six ounces, the latter four.) 

Pepe’s old wood dining room is covered with knickknacks as varied as those found in Grandma’s attic, including photos of famous people and nobodies, a nude painting, nautical bibelots, and scenes of old Key West. Each varnished booth is outfitted with a shelf that holds about a dozen different hot sauces. Outback is a bar where locals congregate. And to the side, on an open patio strewn with mismatched tables, illumination is provided by an array of fixtures that includes a crystal chandelier, green-shaded billiard lamps, and Christmas lights strung among the trees. 

Another good place to dine with locals is THE DENNIS PHARMACY LUNCHEONETTE, where the scent of liniment from nearby aisles competes with that of grilling sandwiches. Come early for thick espresso or café con leche with lengths of hot buttered bread, and at noon for picadillo (spicy ground beef spiked with olives) or handsome Cuban sandwiches (Dagwood heroes of ham, pork, and cheese) or a classic lunch-counter cheeseburger at the blond laminate double-horseshoe counter. 

The Dennis Pharmacy has special appeal for anyone who enjoys roadside hyperbole. Signs out front and in back declare it to be THE SOUTHERNMOST PHARMACY IN THE CONTINENTAL UNITED STATES. In the neighborhood, other signs proclaim the southernmost motel, deli, car clinic, hockey club, guest house, and private house; at the alleged southernmost point itself, marked by a huge concrete buoy (installed because souvenir hunters kept stealing the little sign), travelers from around the world line up to pose for pictures with the Straits of Florida in the background. 

When you consider that Key West’s EL SIBONEY is just ninety miles from Cuba—closer to Havana than to Miami—you understand why its Cuban food tastes so right. Here is the best restaurant on the island for tasting grilled garlic chicken, a half-bird with a crisp skin and meat so tender it slides off the bone when you try to cut it. The fried plantains that come with it are slightly crusty and caramelized around their edges. And yuca, a vegetable served with roast pork, beans, and rice, is a revelation. Glistening white hunks, reminiscent of a well-baked potato, but more luscious and substantial, are served in a bath of heavily garlicked oil and garlanded with onion slices. El Siboney is a clean, pleasant place, its tables topped with easy-wipe plastic and silverware presented in tidy little paper bags. The waitresses guide you through the menu. Ours explained that the Siboneys were Cuban Indians, and that the Indian-themed art on the walls is a tribute to them. 

Key West culture is hard to define, but one thing about it is certain: It is, diverse. Today’s chefs—drawing upon talents and traditions that include the heritages of Caribbean immigrants and Bahamian-ancestored Conchs as well as those of a constant influx of restless creative souls from all over who find their home at the end of the Overseas Highway—have developed a genuine Conch cuisine. 

In particular, we are thinking of the PALM GRILL, a debonair enclave apart from the downtown hustle with a menu of such fusion delights as snapper Antigua baked with capers and gilded with Key lime butter sauce and Cuban pork Wellington, in which black bean pâté stands in for duxelles tucked under a brioche shell. With its textured grass-cloth wallpaper and glowing wall sconces, the Palm Grill is a nice setting for a meditative or intimate meal. Warm bread, featherlight in the Cuban style, perfumes the air as it is presented to diners, piece by piece; soft napery and a thick carpet make quiet conversation possible. When the bill arrives, it is accompanied by slivers of sun-dried mango and a slightly incongruous postcard of the cheesecake portrait of a nude nymph that overlooks the maitre d’s station in the front room. “She is our good luck charm,” explains the waiter, slightly abashed, when he sees us staring. 

When you go out for dinner in Key West, you want more than fine food, however. You want a view of the water and plenty of fresh air. You want a table at LOUIE’S BACKYARD—on the multileveled terrace overlooking the Atlantic, where pleasure boats sail past and pelicans graze the waves. This gracious pink classic-revival house could serve TV dinners and it would still be irresistible on a moonlit night; but it happens to be one of the innovators of Key West cuisine, known for such tropical delights as Bahamian conch chowder with bird-pepper hot sauce, grilled local shrimp with salsa verde, and cracked conch with pepper jelly and ginger daikon slaw. The Louie’s supper we remember best is grilled strip steak with a chipotle chili glaze, garlic mashed potatoes, and red-onion corn relish, followed by a feathery Key lime tart. It was perfect! But who’s to say that our judgment wasn’t swayed by the romance of the setting? It was after dark. Soft island breezes made hurricane lamps flicker. Bulbs strung among branches in overhead trees formed a radiant canopy above the patio; and the ocean glowed cobalt blue as a distant, soundless lightning storm at sea ignited over the horizon. 

The Dennis Pharmacy Luncheonette (permanently closed)

1229 Simonton Street 

Key West, FL

El Siboney

900 Catherine Street 

Key West, FL

Louie’s Backyard

700 Waddell Avenue 

Key West, FL

Palm Grill (permanently closed)

1208 Simonton Street 

Key West, FL

Pepe’s

806 Caroline Street 

Key West, FL

Ricky’s Blue Heaven

729 Thomas Street 

Key West, FL