These islands—numbering more than 800—have long attracted fishermen, divers, and misfits of all shapes and sizes, among them Ernest Hemingway, Truman Capote, Jimmy Buffett, and other members of a mythology that sometimes overshadows an even more diverse reality. Anyone from redneck to urban sophisticate is welcome here. All that's required is an open mind, a taste for fresh grouper, and an affinity for warm water.
THE LAY OF THE LAND
The 113-mile string of islands is divided into three areas. The Upper Keys stretch from Key Largo to around Layton, and encompass dive shops, country clubs, condos for weekend refugees from Miami, and Islamorada, the "sportfishing capital of the world." The Middle Keys, with some of the islands' loveliest stretches, are dominated by Marathon, a small, homely town. The Lower Keys are green and quiet, until you reach the relative metropolis of Key West.
Most of the Keys are connected by one road, which doesn't require a name (though it's officially known as both U.S. 1 and the Overseas Highway). The descendant of Henry Flagler's Florida East Coast Railway, it's essentially the only land route through the Florida Keys. This makes it ideal for the easily disoriented—all you need to know is the nearest mile marker (MM)—but it can be a traffic nightmare. For alleviating the monotony, there are gorgeous views of the water on either side and signs advertising BIG-ASS PRIME RIB and FISH SO FRESH IT SHOULD BE SLAPPED.
Related: Changing Florida Keys
WHAT TO DO
The point, really, is to spend as little time on the road as possible and to stay on the water, under the water, or on a barstool with water lapping just beneath.
DIVING The only living coral reef in the continental United States (and the third-longest in the world) lies just off Key Largo. Within John Pennekamp Coral Reef State Park and the Florida Keys National Marine Sanctuary is an extraordinary underwater universe: canyons and mountains of living rock, schools of fish moving in synchronized Technicolor, shipwrecks, and oddities like the Christ of the Abyss, an 11-foot bronze statue.
A wealth of outfitters are eager to take you diving or snorkeling. The better-respected include Tavernier Dive Center (MM 90.7 Oceanside, Tavernier; 305/852-4007; www.tavernierdivecenter.com); Quiescence Diving Services (MM 103.5 Bayside, Key Largo; 305/451-2440; www.keylargodiving.com); and, despite the bad pun, Amy Slate's Amoray Dive Resort (MM 104.2 Bayside, Key Largo; 305/451-3595; www.amoray.com).
FISHING There's no place you can't fish in the Keys, but Islamorada, Marathon, and Key West are where the charter boats conglomerate. There's a boat for you, whether you want to tackle tuna in the Gulf Stream, troll the reefs for grouper, or stalk the flats of Florida Bay (the "backcountry") for tarpon. For information on charters, boat rentals, and licensing, contact one of the temples of this regional religion: Holiday Isle Beach Resort & Marina (MM 84 Oceanside, Islamorada; 305/664-2321; www.holidayisle.com); Bud n' Mary's Fishing Marina (MM 79.8 Oceanside, Islamorada; 305/664-2461; www.budnmarys.com); or the World Class Angler (5050 Overseas Hwy., Marathon; 305/743-6139; www.worldclassangler.com). A half-day of offshore fishing will run about $600 for up to six people; a half-day backcountry trip is $300 or so for two; and reef fishing in a 50-person "party boat" costs about $30 a head.
KAYAKING Bill Keogh, owner of Big Pine Kayak Adventures (Big Pine Key; 305/872-7474; www.keyskayaktours.com), is a soft-spoken nature photographer and amateur marine biologist who will guide you through the flats and islets of the backcountry around Big Pine and No Name keys. As you glide over the pondlike water, you'll see nurse sharks, turtles, stingrays, sponges, and barracudas. Paddling up a creek through a mangrove forest, using moist, gnarled roots to pull yourself past tree trunks coated with hundreds of tiny crabs, is like entering a primeval universe.
CRABBING Ever wondered where Joe's Stone Crab in Miami Beach gets the gall to charge some $50 for a portion of claws?The answer, sort of, comes from Keys Fisheries Market & Marina (end of 35th St., Marathon; 305/743-4353; www.keysfisheries.com), the harvesting affiliate of the famed restaurant. You'll go out on a commercial boat to see how labor-intensive the work is. A typical 12-hour run (yours will be much shorter) involves pulling 600 traps, each yielding a pound of claws on a good day. The business is extremely competitive, and complicated by a short season, theft, and strict environmental regulations. The crabs themselves are tough fighters: they can break your fingers with their claws. Still, it's an enjoyable, and educational, excursion. Best of all, you get to take home (or devour on the spot) whatever you catch.
The term resort applies loosely in the Keys: many places thus labeled consist mostly of a tiki hut, picnic tables, a hammock strung between two palms, and a cement-block building that needs a fresh coat of pink paint. There are, however, several exceptions.
UPPER KEYS Kona Kai Resort & Gallery Owned by a couple who quit their New York jobs to decompress in the Keys—a familiar story line down here—Kona Kai is small and unpretentious. The 11 rooms, in four low-slung tin-roofed buildings, are furnished simply but thoughtfully (rattan footstools, ceramic tile floors, 340-thread-count sheets). The hotel is arranged around gardens of orchids, palms, and gumbo-limbos and a mosaic-covered pool surrounded by hydrangeas and hibiscus. 97802 Overseas Hwy., Key Largo; 800/365-7829 or 305/852-7200; www.konakairesort.com; doubles from $247.
Cheeca Lodge & Spa The resort's name is not an Indian word, but rather the combined names of Cynthia "Chee" and Carl Twitchell, the A&P heirs who established the hotel in 1961 as an exclusive retreat for the well-heeled. George Bush père is a frequent guest, golf and fishing are the presiding passions, and Yankee-style understatement is the guiding aesthetic, with interiors clearly descended from a different era. Of the 203 rooms, the most desirable are the renovated deluxe beachfront bungalows. Besides the par-three executive golf course, there's tennis, windsurfing, Camp Cheeca for the kids, and a 5,000-square-foot spa. MM 82 Oceanside, Islamorada; 800/327-2888 or 305/664-4651; cheeca.rockresorts.com; doubles from $159.
Moorings Village The yin to Cheeca's yang, the Moorings is passive, discreet, subdued—and right next door. There's no bellhop to lead you to your Bahamian-style cottage or to point out the Balinese furniture and artifacts, large soaking tubs, and well-appointed kitchens. No housekeepers come (unless you ask). There's no room service. You're left utterly alone to enjoy this converted coconut plantation, the hammocks and beach chairs expertly positioned on sand brought in from the Caribbean. Proprietor Hubert Baudoin, a windsurfing Frenchman, sometimes rents the place out for photo shoots, which is why you might see models reclining on the trunks of wind-bent palms. But most of the time you'll see no one at all. 123 Beach Rd. (MM 81.6 Oceanside), Islamorada; 305/664-4708; www.themooringsvillage.com; doubles from $200 (two-night minimum), cottages from $3,325 a week.
MIDDLE KEYS Hawk's Cay Resort This 60-acre playground is geared largely toward families, sportsmen, and conventioneers. Besides the 177 guest rooms, there are 269 villa units and an 85-slip marina. Yes, it's gargantuan, and it can feel crowded, but the resort provides plenty of opportunities to filter out the noise and focus your mind—whether on a tennis ball, the massage you're getting at the brand-new spa, or the tug at the end of your fishing line. Hawk's Cay is renowned for its kids' activities: a water slide in the shape of a pirate ship, movies by the pool, miniature golf, even teen facials. 61 Hawk's Cay Blvd. (MM 61 Oceanside), Duck Key; 800/432-2242 or 305/743-7000; www.hawkscay.com; doubles from $250, villas from $425.
LOWER KEYS Little Palm Island The theme of this resort could be Gilligan's Island set in the Raj. There are 30 duplex units on a mere six acres, so privacy, while respected, is secondary to a sense of isolation. After all, only a select few are willing to spend upwards of $895 a night in the Keys, meals excluded. What do you get for all that?Enthusiastic and diligent service. A roomy suite under a thatched roof, with ocean viewsand bamboo-enclosed outdoor showers. And thoughtful touches like your name in wood blocks above the door. 28500 Overseas Hwy. (MM 29 Oceanside), Little Torch Key; 800/343-8567 or 305/872-2524; www.littlepalmisland.com; doubles from $895.
KEY WEST HOTELS
The question of where to stay in Key West mirrors, in a way, the town's own existential dilemma. Guesthouses represent the past—eccentric, architecturally distinctive. Resorts signify Key West's evolution into a mainstream destination. At one extreme are inns campy enough to make Liberace look like Charlton Heston; at the other, properties much like those anywhere else in America. Between the two poles, however, are places of character and comfort, listed here.
Artist House This fabulous purple Victorian mansion has seven rooms and adornment to spare. Traditional Southern elements predominate: wingback chairs, four-poster beds, acres of swag—enough to make you want to put on a hoopskirt and a bustle. 534 Eaton St.; 800/582-7882 or 305/296-3977; www.artisthousekeywest.com; doubles from $139.
Gardens Hotel Peggy Mills bought this 1870's house in 1930 and set about creating a showpiece botanical garden. She brought in 87,000 paving bricks, a Moorish fountain, and four tinajones, huge earthenware jars from Cuba that each weigh a ton. After her death, the place became a hotel with 17 rooms spread among five buildings. Breakfast—croissants, Key lime beignets—is served in the solarium. But you'll spend more time lolling in the pool, smelling the jasmine, and drinking a toast to Miss Peggy. 526 Angela St.; 800/526-2664 or 305/294-2661; www.gardenshotel.com; doubles from $265.
Heron House The three-building property is distinguished by artistic touches, such as stained-glass transom windows, intricately patterned brick patios, and acollection of rare orchids. The 23 rooms are large, with private decks and high ceilings; walls of teak or cedar marquetry add warmth. 512 Simonton St.; 800/294-1644 or 305/294-9227; www.heronhouse.com; doubles from $189.
Island City House Hotel This 24-room compound includesan 1880's mansion fronting the street whose 12 "parlorsuites" are decorated with Victorian antiques—somewhat dark for the Keys. The gingerbread-trimmed Arch House, over the old carriage entrance, has brighter interiors but simpler furnishings; rooms in the old cigar factory are larger, each with a hammock overlooking the pool. 411 William St.; 800/634-8230 or 305/294-5702; www.islandcityhouse.com; doubles from $210.
Lightbourn Inn A 1903 Queen Anne house on a busy street conceals an astonishing display of compulsive knickknackery: autographed pictures of movie stars; antique furniture, lamps, and objets from around the world; and an entire wall of teddy bears. Breakfast is served by the pool—on Fiestaware, of course. 907 Truman Ave.; 800/352-6011 or 305/296-5152; www.lightbourn.com; doubles from $178.
Marquesa Hotel When it opened in 1988, the Marquesa raised the bar among Key West hotels. The original building, a landmark 1884 Greek Revival boardinghouse, was bought by two local men who specialized in restoring Key West's architectural gems. They furnished the 27 rooms with iron four-posters, pine sleigh beds from Indonesia, English armoires, and planter's chairs from the Caribbean. The Marquesa's courtyard—two small pools surrounded by tropical plantings—is exquisite. Service is graciousness defined: a glass of white wine when you check in, a receptionist who remembers your name when you call six months later. Hands down, the best place to stay in Key West. 600 Fleming St.; 800/869-4631 or 305/292-1919; www.marquesa.com; doubles from $275.
Simonton Court The former cigar factory turned 26-room hotel is made up of several structures, including a Gothic Revival manse with mazelike staircases; a cigar maker's shotgun house; and Bahamian-style cottages. Some rooms have rather ordinary furnishings; those in the mansion and the town house are generally more inspired. 320 Simonton St.; 800/944-2687 or 305/294-6386; www.simontoncourt.com; doubles from $209.
KEY WEST RESORTS
There are several standouts among the island's larger properties. The 311-room Wyndham Casa Marina Resort (1500 Reynolds St.; 800/626-0777 or 305/296-3535; www.wyndham.com; doubles from $359), built by Henry Flagler in 1920, is reminiscent of other Florida land-boom hotels. The beautiful grounds slope down toward a large beach. A nearby sister property, the pink concrete Wyndham Reach Resort (1435 Simonton St.; 800/626-0777 or 305/296-5000; www.wyndham.com; doubles from $329), has a smaller beach and similar resort amenities; all 150 rooms have balconies. • The Pier House Resort & Caribbean Spa (1 Duval St.; 800/327-8340 or 305/296-4600; www.pierhouse.com; doubles from $290) established its reputation in the late sixties and has been coasting ever since. It's a large complex near Mallory Square with a popular beach and three restaurants. Rooms in the Caribbean Spa building are best. • The Hilton sits on the Old Town waterfront, but Sunset Key Guest Cottages (245 Front St.; 888/477-7786 or 305/292-5300; www.sunsetkeycottages.hilton.com; cottages from $485) is its ace in the hole: a semi-private island 10 minutes away by launch, with a beach, restaurant, bar, and 37 bungalows. • The 120-room Hyatt Key West Resort & Marina (601 Front St.; 800/554-9288 or 305/296-9900; www.hyatt.com; doubles from $325) is one of the smallest of the large resorts, and has a low-key feeling. • Smaller yet is Ocean Key Resort (No. 0 Duval St.; 800/328-9815 or 305/296-7701; www.oceankey.com; doubles from $399), founded by the owners of Little Palm Island, who bought a characterless building at the foot of Duval Street and sank $5.5 million—and a lot of bright paint—into it. Book a room overlooking Mallory Square: all you'll remember seeing is the sun dropping below the horizon.
A Florida Keys diet is bound to be plentiful in omega-3 and other fishy nutrients, but you'll get points off for breaded and fried. Thankfully, restaurants are warming to the healthful New World cuisine—tropical fruits and tubers, Latin-Caribbean flavors—that's ubiquitous in Miami and points north. In other words, the shrimp may be fried, but it will come with a mango-poppy seed dipping sauce. In the land of the laid-back, "formal" restaurants are happy to see you wearing a shirt and shoes. (Seriously: A jacket is never required; ties are laughed at.) At dockside seafood joints, fresh fish and talkative bartenders are the only prerequisites.
UPPER KEYS Fish House The line is long, the conch chowder peppery, and the catch of the day done eight ways (try Matecumbe-style: tomatoes, capers, shallots, basil, and lemon juice). And the nautical knickknacks lining the walls and strung on the ceiling are endlessly amusing. 102401 Overseas Hwy., Key Largo; 305/451-4665; dinner for two $55.
Pierre's The most elegant restaurant in the Upper Keys is the creation of Hubert Baudoin, owner of the Moorings across the highway. Chef Dino Taglione does wonders with seafood—yellowtail crusted in lotus root and served over a chile-flecked soba-noodle salad, grouper with artichoke-mushroom hash in a salmon-roe beurre blanc. Baudoin fitted the plantation-style house with ancient monastery doors from Tibet, archways from India, and rugs from Morocco. 81600 Overseas Hwy., Islamorada; 305/664-3225; dinner for two $130.
Snapper's Waterfront Seafood Restaurant On a mangrove-ringed inlet in Key Largo, Snapper's brings in the locals with killer rum drinks and good appetizers: cracked conch, blackened dolphin "fingers." All deep-fried items are hand-breaded, thank goodness. MM 94.5 Oceanside, Key Largo; 305/852-5956; dinner for two $70.
MIDDLE KEYS ChikiTiki Bar & Grille Hidden away in a Marathon marina, ChikiTiki serves dockside grub with Mexican touches, such as a green-chile cheeseburger and spiced fries. In most other ways, however, it's an archetype of its genre: the smell of sea air; a bar crowded with salts of all types. And, yes, that's a mousetrap holding down your bill. 1200 Oceanview Ave., Marathon; 305/743-9204; dinner for two $20.
LOWER KEYS No Name Pub This pub was established in 1935, which may be the last time it got a thorough cleaning. At least the dollar bills covering every square inch of wall and rafter seem to have been there forever, as have the characters wearing beards and trucker caps and eating tangy smoked-fish dip and grouper sandwiches off paper plates. The point is to be pleased with yourself for having found the place. N. Watson Blvd., Big Pine Key; 305/872-9115; dinner for two $35.
KEY WEST Alice's at La Te Da Go for a poolside table among the palms at the campy La Te Da guesthouse. Then go for the yellowtail snapper in Key lime beurre blanc, the "magic meat loaf," or the rack of Australian lamb. Most of all, go to meet Alice Weingarten, the island legend who visits every table wearing a floppy toque and cat's-eye glasses—the consummate Key West hostess. 1125 Duval St.; 305/296-6706; dinner for two $70.
Blue Heaven Restaurant In a former bordello allegedly frequented by Ernest Hemingway—hardly a unique claim in Key West—Blue Heaven is huge among the locals for a lively bar and breakfast in the backyard, complete with picnic tables and clucking chickens. It might seem untoward to eat eggs in such company, but the omelettes shouldn't be missed. 729 Thomas St.; 305/296-8666; breakfast for two $20.
Café Marquesa Adjoining the Marquesa Hotel, the café offers a dining room filled with sunshine during the day and illuminated by candles in the evening. Chef Susan Ferry, who trained under star Miami chef Norman Van Aken (of Norman's), changes the menu daily, adding Mediterranean and Asian touches to Caribbean and Latin American specialties. 600 Fleming St.; 305/292-1919; dinner for two $120.
Louie's Backyard Van Aken made his reputation here before being anointed king of New World cuisine. But Louie's maintains its status as an institution and is still a favorite among residents, despite the crush of tourists feasting on the innovative Caribbean-influenced food: lobster braised in truffle butter; grilled tuna served with a sweet soy, papaya, and seaweed salad. The "backyard" is really the Atlantic. 700 Waddell Ave., Key West; 305/294-1061; dinner for two $90.
In a place where a plastic daisy on your flip-flops counts as a stylistic flourish, don't expect to find exceptional retail opportunities. There are a few specialty shops worth mentioning (all but the first are in Key West). World Wide Sportsman (81576 Overseas Hwy., Islamorada; 305/664-4615; www.basspro.com), an enormous sportfishing store, sells every type of rod and fly imaginable; there's a replica of Hemingway's boat Pilar in the center. • T-shirt shops have taken over Duval Street, Key West's main drag, like kudzu; for worthwhile gifts, try Fast Buck Freddie's (500 Duval St.; 305/294-2007), an old-time department store. • The local answer to Kiehl's, Key West Aloe (524 Front St.; 305/294-5592) is full of lab-coated assistants eager to administer to your sunburn. • They may not fly back home, but the colorful, boisterously patterned shirts and dresses at Key West Handprint Fabrics & Fashions (201 Simonton St.; 305/294-9535) are pretty much the town uniform. • Key West claims to have been the home of 11 Pulitzer winners; the best bookstore is Key West Island Books (513 Fleming St.; 305/294-2904). • If you must have one of those manatee-shaped mailboxes you've seen lining U.S. 1, Pelican Poop (314 Simonton St.; 305/296-3887) is the place to buy it. • Of the dozen or so more-serious art galleries on the island, check out Gallery on Greene (606 Greene St.; 305/294-1669), representing local and Cuban artists, and the Haitian Art Co. (600 Frances St.; 305/296-8932), crammed with paintings, sculptures, and voodoo flags.
BEST OF THE KEYS
park it here
The most compelling detour off U.S. 1 comes up before you even enter the Keys: Card Sound Road, which connects the mainland with the top half of Key Largo. Less trafficked, the byway is lined with mangroves, canals, and locals selling blue crabs. • The shops at Treasure Village (MM 86.7 Oceanside, Islamorada; 305/852-0511) are skippable, but the giant, anatomically correct lobster is worth inspecting, as is April Fool, at 71 inches the smallest sailboat ever to cross the Atlantic. • On the docks at Robbie's of Islamorada (MM 77.5 Bayside, Lower Matecumbe Key; 305/664-9814; www.robbies.com), you can feed the tarpon, which jump out of the water to grab bait from your hand. • Lignumvitae Key Botanical State Park (305/664-2540) is a 280-acre virgin forest—one of the few places in the world to see old-growth gumbo-limbo, mahogany, lignum vitae, and fig trees.
BEST OF THE KEYS
Protected by a coral reef, the 113-mile stretch from Key Largo to Key West isn't lined with luscious white sand. But there are a few beaches worth a mention. Anne's Beach, a mere blip on Lower Matecumbe Key, has picnic tables, a boardwalk, and just enough sand to keep your toes happy. • On Big Pine Key, Bahia Honda was nearly wiped out by Hurricane Georges in 1999. Since rebuilt, it's once again a lovely crescent of sand with good swimming and views of a remnant of the old Flagler Railway bridge. • In Marathon, the family-oriented Sombrero Beach is perhaps the best thing about the otherwise grotty town. • The beaches on Key West can get as hectic as Mallory Square at sunset. Beat the crowds by going to Fort Zachary Taylor Historic State Park, which has clear, deep water and a perfect—and perfectly unknown—location for watching the sun go down.
BEST OF THE KEYS
eat your dessert
Every other restaurant in the Keys claims to have the best Key lime pie. Manny & Isa's (MM 81.6 Oceanside, Islamorada; 305/664-5019) may well be the winner. This Cuban joint sells pie by the slice ($3.50) that has the perfect amount of meringue, a pleasingly flaky crust, and a filling that tastes the way Key lime filling should. Few lime trees are left in the Keys, so most chefs use imported fruit or resort to bottled juice, but Manny collects the limes from his backyard and squeezes them himself. • If Manny runs out of pie—as he often does by mid-afternoon—there are plenty of runners-up. A close second is Little Palm Island (28500 Overseas Hwy., Little Torch Key; 305/872-2524), where the pastry is made with cashews, and whipped cream is used instead of meringue. • At Alice's at La Te Da (1125 Duval St., Key West; 305/296-6706), the pie's tartness is leavened by a layer of chocolate ganache. • Louie's Backyard (700 Waddell Ave., Key West; 305/294-1061) makes a fancified version, with a gingerbread crust and raspberry coulis.
BEST OF THE KEYS
getting lit: essential reading
Dozens of writers have found inspiration in the beauty and moods of the Florida Keys, but perhaps none captures the island as eloquently and, for the traveler, as helpfully, as Joy Williams in The Florida Keys: A History and Guide (Random House). A deft storyteller and smasher of myths, Williams has produced a guide that is funny and highly opinionated (though sometimes overly disdainful of luxury). For a more literary context, the required volumes include Hemingway's To Have and Have Not (Simon & Schuster), an imperfect novel that nonetheless portrays the ambience of his Key West; Thomas McGuane's Ninety-Two in the Shade (Random House); and The Key West Reader (Tortugas), a good compilation of renowned writers.
BEST OF THE KEYS
clichés worth doing (once)
SUNSET AT MALLORY SQUARE Key West's legendary freak show—the contortionist, the fire juggler, the escape artist—must be seen once. The Rouse-ified square brims with the pink-faced and inebriated, but it's a tradition to uphold.
CONCH FRITTERS Local conch is endangered, so the fried bits on your plate (or the chewy bits in your chowder) probably came from the Turks and Caicos. In any case, conch is the local version of escargot: a mere beast of burden for more eminent accompaniments, whether cocktail sauce or the hot-pepper jelly and wasabi served at Louie's Backyard.
HEMINGWAY'S KEYS Papa's ghost is inescapable here, especially in Key West, where he lived for nine years. The museum in his former house and writing studio (907 Whitehead St., Key West; 305/294-1136; www.hemingwayhome.com) is an exercise in imagination-stretching: here Hemingway sat, here he wrote, here he swam, here he argued with his wife. But to replicate Hemingway's life, you need to go elsewhere, like the bar at Sloppy Joe's, or fishing at sea, where he was happiest.