The Florida Keys are sometimes called America's Caribbean, and they exude an end-of-the-road remoteness and a languid tropicality that rivals the West Indies in appeal

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.

DESTINATION RESORTS
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.

 

RESTAURANTS
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.

SHOPPING
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
beaching it
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.

No Name Pub

Manny & Isa's

Louie's Backyard

Housed in an oceanfront Victorian house, this Caribbean-American restaurant has been a local favorite for more than three decades. The airy dining room is designed with white tablecloths and wood-shuttered windows, although guests often prefer to dine outside on the multilevel deck overlooking the Old Bahama Channel. Using locally caught seafood and produce grown specifically for Louie’s by Island Farms, longstanding chef Doug Shook creates fresh, seasonal (and pricey) dishes like Bahamian conch chowder and seared yellowfin tuna with wasabi sweet soy. Upstairs, the wine bar provides panoramic ocean views and a more affordable menu of small plates.

Dining Room at Little Palm Island

Situated on a small private island, this oceanfront resort restaurant was chosen by Travel + Leisure as one of the nation’s most romantic dining destinations. Tiki torches light the path to the restaurant, which is decorated with hardwood flooring, classic white tablecloths, and large windows overlooking the water. Additional seating is available on the open-air terrace, and a few tables are set up by the water’s edge, where wild deer often approach to nibble the rose petals strewn across the sand. Combining French and Latin flavors, the menu includes dishes like coconut lobster bisque, and mahimahi with cilantro polenta.

Fish House

As it's name suggests, the Fish House spotlights fresh, local catch like black grouper, cobia, and conch. The dining room is decorated with seafood-themed art and strings of lights, but seating is also available at umbrella-shielded tables in front of the blue building. The restaurant is known for a dish called matecumbe — usually snapper or grouper, baked and covered with tomatoes, capers, basil, and olive oil. The deep menu also touts choices like conch chowder, smoked fish dip, and lump crabcakes. In accord with its Florida Keys location, the Fish House also has housemade Key lime pie for dessert.

ChikiTiki Bar & Grille

This restaurant at Burdines Waterfront is known for its burgers, fried fish, fried key lime pie, as well as its views of the sea, boats, and Boot Key’s mangroves. The Chiki Tiki consists of an upstairs hut with a thatch roof, surrounded by a dining deck the color of tropical shallows. Inside are more tables, a bar, and license plates on the walls. The menu includes such options as green chile cheeseburgers, a shrimp basket with hush puppies and slaw, and fried, grilled, and blackened fish sandwiches. Guests can bring their own caught-and-cleaned fish to the Chiki Tiki chefs for cooking.

Café Marquesa

This intimate, 50-seat restaurant is located in the Marquesa Hotel, a collection of 19th-century conch houses in historic Old Town. Tall windows overlook Fleming Street, while a display kitchen provides views of chef Susan Ferry and her team at work, creating contemporary American dishes from the small, daily changing menu. Options may include ginger coconut—crusted mahi mahi and pan-roasted duck breast with red curry coconut sauce. The restaurant also has a small bar area serving small plates, reasonably priced wine, and Key West—inspired cocktails like the Island Dingy, made with spiced rum, coconut rum, and fresh fruit juices.

Blue Heaven Restaurant

Pierre's

Snapper's Waterfront Seafood Restaurant

A neighborhood staple since 1989, this oceanside seafood joint combines Caribbean cuisine with a Florida vibe. A three-part endeavor, Waterfront is a restaurant, tiki bar, and outdoor deck, also known as The Turtle Club. The interior atmosphere is equal parts fisherman hangout and Keys-inspired romance with a 350-gallon saltwater fish tank, coral architecture, splashes of bright color, and long wooden bars stacked high with pints and wine glasses. Live Jazz brunches on Sunday mornings entertain locals and guests alike. Menu items include an assortment of seafood, such as ceviches, tuna nachos, and fresh seasonal fish, cooked to order.

La Te Da

This recently renovated hotel restaurant hosts its very own cabaret; men in drag do nightly impersonations of celebrities like Madonna and Cher at the Crystal Room. Skip the overpriced poolside restaurant for a fresh mojito on the black-and-white-marble patio.

Created by the editors of T+L for Regent Seven Seas Cruises.

Marquesa Hotel & Café Marquesa

1884 clapboard houses set back from busy Duval Street. A no-cell-phones-in-public-spaces policy helps to keep the peace.

 

Little Palm Island Resort & Spa

Sunset Key Cottages, a Luxury Collection Resort

The Pier House Resort & Spa

Six low-rise buildings, tucked into bougainvillea gardens between the harborfront and the historic Old Town, house 142 guest rooms and suites. The luxury resort maintains an authentic Old Key West attitude with help from local art and the Chart Room Bar, which continues to serve free popcorn and steers clear of any neon slushie drinks. Book one of the new ocean view suites, with a balcony outfitted with a wet bar and idyllic views of the Gulf of Mexico.

Reach Resort

The sister property to the Casa Marina, features an outpost of the Strip House.All 150 breezy rooms at the Reach Resort have coconut-shell headboards, bathrooms with abstract art, and private balconies.

Simonton Court

This adults-only private resort covers two secluded miles in the center of Old Town. Select five different styles of accommodations for a total of 30 rooms: B&B at The Mansion, cottages, an inn, Manor House, and a townhouse, with concierge services available. Each lodging option has private doors leading to grounds abundant with flowered vines and palm trees, and light-filled rooms have wicker furniture, high ceilings, and plenty of wood accents like painted wood furniture and wall paneling for a high-end cottage feel. Brick walkways guide guests to the four 24-hour pools where a large, complimentary continental breakfast is served daily. 

Lightbourn Inn

Island City House Hotel

This all-suite, 24 room property has three quaint "houses" with one- and two-bedroom suites, each with a porch or balcony where rocking chairs or hammocks can be found. A large pool and sitting alcoves are hidden between lots of foliage, and other amenities include fully equipped kitchens and continental breakfast that is served in the garden. Wood or wicker beds, large oriental rugs, paisley comforters, and simple framed artwork make up the homey, simple interior design, allowing the exterior design and features to be the focal point.

Heron House

This charming establishment is traditional in design, thanks partly to being one of the few homes that wasn’t destroyed by the massive fire on Key West in 1886. Each of the 23 rooms has a lived-in feel thanks to wicker furniture and long-standing, intricate wood and stone elements. There is also stained-glass artwork throughout the grounds. A full continental breakfast buffet is served in the garden, where a small rock and waterfall feature and pool can be found, and the innkeepers also serve a daily wine and cheese happy hour.

Gardens Hotel

Artist House

One of the most photographed Key West homes for its accurately restored Colonial Queen Anne architecture, this Old Town hotel is known for its historic columns and gingerbread elements. This six-room guesthouse has been in operation for more than 30 years and now sports purple shutters and rocking chairs on its verandas. The rooms have plantation shutters with 12-foot ceilings, and to honor the former owners, famous painter Robert Eugene Otto and his musician wife Anne, guests are served complimentary continental breakfasts and daily happy hours in their beloved tropical garden with a pool.

Hawks Cay Resort

Moorings Village Village & Spa

Even after serving as the backdrop for countless fashion-magazine photo shoots, the Moorings Village & Spa— 18 brightly accented cottages connected to the beach by wooden walkways on a former coconut plantation in the Florida Keys—still seems like your own secret discovery. Lush, almost jungle-like landscaping gives way to a private white-sand beach with swaying hammocks and a thatched-roof dock. Palm trees, hammocks, sand: this is as stripped-down as a vacation experience gets, and one you’d swear couldn’t exist among the shell shops and tiki-festooned marinas of the Florida Keys. At sunset, amble across the road for rum cocktails and conch fritters at Morada Bay Beach Café, or do what the regulars do—bring back some stone-crab claws from the market to devour on your porch with a cold beer.

Cheeca Lodge & Spa

Kona Kai Resort & Gallery

With a private white-sand beach, a pool and Jacuzzi, a tropical fruit garden, and 11 guest rooms and suites named after tropical fruits, Kona Kai Resort & Gallery sets a junglelike atmosphere for swinging in a hammock. Bright rooms are stylish with simple furnishings and horizontal wooden blinds, but it is the lush grounds that are the real showstopper. French doors open onto hardwood decks and tiki huts shaded by palms, and paths lead to tennis courts and areas for massage or yoga.

Ocean Key Resort & Spa

Hyatt Key West Resort & Marina

Designed to resemble a large plantation-style home, this resort has 118 rooms, each with tiled-entry foyers and private balconies providing at least partial ocean view. The open-air piazza overlooking the Gulf of Mexico has a heated outdoor pool, whirlpool, and access to the hotel docks with jet skis and other watersports. Decorations include brightly-colored, tropical print upholstery and pillows, wooden lounge chairs, and oversized bath fixtures like a large tiled shower. On-property, there is also SHOR American Seafood Grill and the Blue Mojito Bar and Grill restaurants, plus the full-service Jala Spa. Hypo-allergenic rooms are available as well. 

Casa Marina Resort

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