By: David Appell
The fact that Key West is one of the world's most-recognized vacation destinations begs the question – what is all the fuss about? It's hardly about the beaches (which pale in comparison to others in South Florida). Rather, it's the local sense of sun-drenched hedonism that tourists find contagious – and which is entirely unique to this bit of Florida. Visiting this part of the United States almost feels like you're leaving the country – and in fact, Key West and the rest of the Keys actually attempted to make themselves an independent republic known as the "Conch Republic" in 1982. While the area obviously remained officially associated with the US, this far-flung outpost still celebrates Independence Day every April 23. At the same time, it's maintained its longstanding tradition of tolerance – so whether you're a family, single, or couple (gay or straight), you'll be welcomed in Key West.
Once there, you'll find lush tropical vegetation and Victorian architecture (ranging from dollhouse-cute to mansion-grandiose) that make for street after street of charming little guesthouses and landscaped oases. By night, you can stay up til dawn at the colorful, sometimes rip-roaring, bars that line Duval Street – and spend the next day recovering with any one of a myriad of day cruises offering snorkeling, fishing or, if you wish, just plain drinking. But Key West is more than just a pretty party town – far from it in fact. A wealth of attractions and museums relating to its rich literary, maritime, and other history, plus a slew of interesting little shops to browse – all of it with the gleaming, glittering, ever-present sea as a backdrop. Add to that a quirkiness that comes across in the traditionally irreverent, salty personalities of the locals (dubbed Conchs, after the island's symbol, a mollusk with the distinctive pink seashell) – some go back generations, some are brand-new to the island, but almost all came check out of the mainstream rat race, and perhaps find their very own Margaritaville.
If you've only a few days to spare to find your lost shaker of salt, don't fret, as three days is enough time to get a good sense of Key West. Rent a moped from one of the many providers and cruise the streets to ogle the beautiful Victorian-style homes it's famous for, tour the Hemingway House and see the famous six-toed cats that roam the property, experience the sunset celebration in Mallory Square, and stroll the length of Duval Street after dark. If you have five days, do all of the above, but also hit the beach and catch some rays, book yourself on a day cruise of snorkeling or fishing, and pose for a photo at the "Southernmost Point in the US." If you have a week to spare, balance your time in Key West with a side trip or two – there are several other Keys worth exploring and Miami is just a few hours away. The bottom line at this end of the line is that the spirit of Key West is all about letting go – of your worries, of your hang-ups, of your real life. If you don't have fun here, well, to paraphrase Jimmy Buffett, that's your own damn fault.
For an overview of Key West and some insight to its colorful history, we recommend taking a tour – perhaps more than one. The open-air Conch Tour Train (303 Front Street; daily 9am-4.30pm; 800/868-7482; $22.50; www.conchtourtrain.com) has been a classic for a half-century, while the newer Old Town Trolley Tour (Mallory Square; daily 9am-4.30pm; 800/868-7482; $22.50; www.trolleytours.com) has the advantage of allowing you to hop on and off. There's a dedicated Gay & Lesbian Trolley Tour (728 Duval Street; Saturdays 11am; 305/294-4603; $25; www.gaykeywestfl.com/trolleytour) or you can scare yourself silly on the tours headed by the Original Ghost Tours of Key West (430 Duval Street; daily 8 and 9pm; 305/294-9255; $15; www.hauntedtours.com). Parrotheads should make a beeline for Trails of Margaritaville (reservations required; 305/292-2040; $20; www.trailsofmargaritaville.com) where you'll see the first local house lived in by Jimmy Buffett, and the birthplace of a few of the "songs you know by heart."
The Key West Chamber of Commerce (www.keywestchamber.org) and Monroe County Tourist Development Council (www.fla-keys.com/keywest) both offer a wealth of information on activities and tours in Key West. For gay-and-lesbian-specific info, visit the Key West Business Guild (www.gaykeywestfl.com).
If you prefer to explore on your own, most of the “action” is found in the picturesque Old Town, an easily walkable area that dates back to 1822. Bounded by Mallory Square, Fort Zachary Taylor State and White Street, the streets here are loaded with dining and nightspots, plus most of Key West's lodging.
Starting around Mallory Square, one of the oldest attractions in town is the modest 1934 Key West Aquarium (1 Whitehead St.; daily 10am-6pm; $9; www.keywestaquarium.com) set in a white-stucco converted fish market. Sea World it is not, but it nonetheless makes a nice detour and houses sharks and stingrays in addition to local fish; the kids will certainly enjoy the touch tanks that provide hands-on interaction with the residential marine life. Across the way, the Shipwreck Historeum (1 Whitehead St.; Wed-Mon 9.45am-4:45pm, Tues 9:45am–6:45pm; $9; www.shipwreckhistoreum.com) is more than just hokey schtick (obviously designed to appeal to the kids) – it ultimately delivers a compelling look at the island's early shipwreck-salvaging history through exhibits centered around the Isaac Allerton, a prominent wreck from 1856. You can even watch an entertaining movie and visit the lookout deck for one of the island's best bird's-eye views.
One block over, the imposing red-brick 1891 Custom House, with its dramatically steep gables, now houses the Key West Museum of Art & History (281 Front St.; Mon-Fri 10am-3pm, Sat-Sun 9am-5pm; 305/295-6616; $10; www.kwahs.com/customhouse.htm), which affords a good look back at the heritage that has made Key West the unique place it is. Right across the street (look for the cannons out front), gold-diggers and history buffs alike will get a kick out of the Mel Fisher Maritime Museum (200 Greene St.; daily 9.30am-5pm; $11; www.melfisher.org), a two-story monument to treasure hunter Mel Fisher's big score of 1985: a treasure bounty worth millions, courtesy of a pair of Spanish galleons that went down in a storm in 1622.
A short distance away is the two-story Audubon House & Gardens (205 Whitehead St.; daily 9.30am-5pm; $10; www.audubonhouse.com), once actually the home of a sea captain's family, but allegedly the site where legendary naturalist/artist John James Audubon sketched some birds during a 1832 visit; regardless, it's a gracious look into the past and boasts an acre's worth of lovely gardens. Walk east to the old Naval Yards and current Truman Annex and you'll find an even more singular spot: Florida's only presidential meseum, theHarry S Truman Little White House (111 Front St.; daily 9am-4.30pm; $11; www.trumanlittlewhitehouse.com); Give 'Em Hell Harry came to Key West regularly (and the place was also used by Eisenhower and Kennedy).
Just down the road, Key West's rounded, southwesternmost extremity is given over to Fort Zachary Taylor State Park (entrance at Southard and Whitehead Sts.; daily 8am-sunset; $1.50; www.floridastateparks.org), whose 87 acres include a fortress built from 1845 to 1866. Besides a pair of daily half-hour tours of the modest fortifications (noon and 2pm), the best thing about the park is the beach at the southern end – Key West's most appealing – where you'll find decent snorkeling, picnic tables, nature trails, and a snack bar. Once you tire of the sand and surf, backtrack just a bit to one of the town's newest tourist attractions: the Pirate Soul Museum (524 Front St.; daily 9am-7pm; $13.95; www.piratesoul.com), marked by a row of Jolly Rogers leering out front. Historically, pirates were never much of a big issue in Key West, but this elaborate multimedia presentation of the history and lore of the Jamaica-based swashbucklers is very well done; it's not without its cheesy aspects aimed at children, but it's also quite educational and has a real pirate treasure chest on display.
The last – or perhaps first, depending on your leanings – important sight to see down at this end of town, is a fairly unprepossessing white-clapboard bit of business on Duval Street. It was spared from being turned into a bar, restaurant, or T-shirt shop because it happens to be the Oldest House/Wreckers Museum (322 Duval St.; daily 10am-4pm; $5; www.keysdirectory.com/oldesthouse), a sea captain's abode built in 1829 that's now an indoor-outdoor museum of 19th-century island life that's not to be missed. For a change of pace, flower lovers shouldn't miss the blossoms in Nancy Forrester's Secret Garden (1 Free-School Lane; daily 10am-5pm; $6, hour-long tours $15; www.nfsgarden.com), just a few blocks away off Simonton Street; the one-acre botanical garden is home to blooms from the mundane and local to the exotic and foreign (from the Seychelles, the mountains of Cuba, and the depths of the Amazon, for example). You can even spend the night at a cottage on the premises.
Don't leave town without checking out the handsome 1851 manse on Whitehead Street connected with Key West's greatest literary legend. Before he moved to Cuba, Papa was a bit less of a rolling stone from 1931-1939, when he lived at what is now known the Ernest Hemingway House (907 Whitehead St.; daily 9am-5pm, $10; www.hemingwayhome.com), where he cranked out many of his novels and short stories when he wasn't fishing or tying one on down at Sloppy Joe's Bar (see Nightlife); his famous cats, some of which have an extra toe, still roam about the place. Right across the street is a mainstay of the island's maritime past, the 1847 Lighthouse Museum (938 Whitehead St.; daily 9.30am-4.30pm; $10; www.kwahs.com/lighthouse.htm); you can climb the 88 steps for a great view and check out the little museum in the adjacent lighthouse-keeper's house.
Back on Duval, a fairly recent addition to the tourist circuit is the colorful and charming Key West Butterfly and Nature Conservatory (1316 Duval St.; 9am-5pm; $10; www.keywestbutterfly.com) built around a miniature park in a greenhouse where 50 to 60 species of the winged wonders flit about and sometimes land on you as you stroll. Also at this end of the island is the Southernmost Point (in the continental U.S., that is) anchored by a cement marker tarted up like a buoy – Cuba is just 90 miles away from here and Cubans escaping Fidel Castro's dictatorship do still wash up on shore every once in a while.
From here, continue up the eastern side of the island along Atlantic and South Roosevelt Boulevards toward the airport and you'll find a pair of small Civil War-era forts, one of which is the West Martello Tower (Atlantic Blvd. at White St.; Tue-Sat 9.30am-3pm; donation optional; www.keywestgardenclub.com), now the headquarters of the Key West Garden Club, whose gardens you can tour. Also along here are two popular beaches, Higgs (Atlantic Blvd. at Reynolds St.) and Smathers (S. Roosevelt Blvd.), both wide strands like those you'd find in northern Miami and Fort Lauderdale, complete with facilities, equipment rentals, and food/drink concessions. By the airport, the Fort East Martello Museum & Gardens (3501 S. Roosevelt Blvd.; daily 9.30am-4.30pm; $6; www.kwahs.com/martello.htm) houses a varied exhibition of Conch history, art, and lore.
Death rarely gets more whimsical than at the Key West Cemetery (701 Passover Lane; daily sunrise-sunset; free) and if you don't take one of the walking tours that stop here (see above), be sure to have a look on your own. The mausoleums are above-ground (because digging into coral rock proved difficult) and some of the inscriptions on them are – believe it or not – a hoot. One quip gives you the flavor nicely: "I told you I was sick." There are some interesting stories here (one in particular about a necrophiliac), so try do try to snag a tour.
Everyone should get out on the big blue sea at least once, whether just puttering around the harbor or out to the offshore reef for some snorkeling. Over on the west side of the island a couple of blocks from Duval Street, a flotilla of pleasure cruises weighs anchor every day, often several times a day. One top choice is the Sebago catamaran (www.keywestsebago.com); the company offers snorkeling, champagne sunset, a glass-bottom, and other excursions, not to mention sundry other water craft and sports. If your tastes run more toward the tall clippers and schooners of yore, check out the Liberty fleet (www.libertyfleet.com). You can incorporate a day sail with a little history-and-beach action by taking the fast ferry called the Yankee Freedom II (www.yankeefreedom.com) to the Dry Tortugas, a group of tiny uninhabited isles 70 miles and 2.5 hours west that happen in fact to be the real tail-end of the Keys. Out here you'll find a national park containing the mid-19th-century Fort Jefferson and some mighty appealing beaches for swimming, sunning, and snorkeling. Finally, there are plenty of niche-interest cruises, too: gay folks should try Blu Q (www.captainstevekw.com) while those who like to let it all hang out can sail out on Skinny Dipper Cruises (www.skinnydippercruises.com).
Lower, Middle and Upper Keys
Down here, U.S. 1 is also known as the Overseas Highway, and appropriately so, as it links this string of 1,700 islands (of which only 45 are inhabited) sprawling 150 miles south from mainland Florida. It's a gorgeous drive that includes over 43 bridges – the most famous being the Seven Mile Bridge between Key Vaca and Little Duck Key – and passes enough sites, resorts, and activities along the way to jam-pack a weeklong vacation. The offshore Florida Keys National Marine Sanctuary (www.floridakeys.noaa.gov) covers 2,800 square miles and includes the most extensive living coral reef in North America and surrounds the entire archipelago of the Florida Keys. The snorkeling and diving are excellent here (though the reefs haven't been doing as well as in years past, experts say the best corals are to be found at Carysfort Reef in the Upper Keys), as do the world-class boating and fishing – here you'll find some of the widest diversity of species in the world, more than 6,000 in open water on the Atlantic side and the backwater/flats on the Gulf side.
Following are some of the main highlights, in order of closeness to Key West: Bahia Honda Key: Bahia Honda State Park beaches. Big Pine Key: National Key Deer Refuge, with shy, adorable miniature Bambis unique to the Keys. Islamorada (pronounced "EYE-la mo-RA-da"): actually comprising several keys, it's home to Windley Key Fossil Reef State Geologic Park, Theater of the Sea, and Lignumvitae Key Botanical State Park. Grassy Key: Dolphin Research Center and Curry Hammock State Park. Marathon: Museum of Natural History of the Florida Keys, Florida Keys Children's Museum, and George Adderly House. Pigeon Key: a railroad museum and old railway-worker cottages. Key Largo: John Pennecamp Coral Reef State Park, Wild Bird Rehabilitation Center, and Dagny Johnson Key Largo Hammocks Botanical State Park.
It's a bit of a haul to Miami and back in one day (the drive is about three hours and change, depending on traffic), so you should try stay for several days if possible. But if you can't, even a day trip can be rewarding. The Art Deco Historic District of the offshore barrier island that is Miami Beach is of course one of America's hottest, sexiest destinations, with a happening beach, hot nightlife, and buzz-worthy dining scene. Over in mainland Miami, don't-miss places include Coral Gables and its historic Biltmore Hotel, Venetian Pool, stately homes, and great shopping/dining on Miracle Mile; Coconut Grove, also a nifty shopping/dining downtown, plus a planetarium, and historic Vizcaya mansion); Little Havana's funky Latin shops, galleries, and eateries; and Everglades National Park (www.nps.gov/ever) in the county's western and southern reaches. For more detailed Miami info, check out our Miami Spotlight.
Although the small, mom-and-pop guesthouse is still the quintessential Key West lodging experience, down here they've got it all, from old-time motels to upscale, full-service resorts. Average room rates are over $200 and in high season, anything below $125 is rare and below $90 is practically miraculous. Minimum stays may be required in some cases, especially in high season. Following is a selection of ten properties that cover most budgets and interests, all have pools unless otherwise noted.
Among luxury lodgings, those looking for some serious pampering in an elegant resort (100 very roomy and high-ceilinged suites), good dining, a spa, and a stellar waterfront location right on Mallory Square and the harbor, Ocean Key (Duval St. at Mallory Square; 305/296-7701 or 800/328-9815; www.oceankey.com) is definitely the ticket. Nearby, the slightly larger Pier House Resort (1 Duval St.; 305/296-4600 or 800/723-2791; www.pierhouse.com) has been an upscale favorite for years and with good reason – two very good restaurants, a full-service spa, and its very own stretch of beach. But if you really crave the quintessential Key West experience – a small, intimate guesthouse – stay at what is probably the most luxurious one in town. The Gardens (526 Angela St.; 305/294-2661 or 800/526-2664; www.gardenshotel.com) has 17 rooms in a 19th-century Bahamian-style mansion listed on the National Register of Historic Places.
On the upper end of our moderately-priced hotel choices is another historic property – the Marquesa Hotel (600 Fleming St.; 305/292-1919 or 800/869-4631; www.marquesa.com) is an award-winning small hotel (just 27 rooms) with the feel of an upscale B&B throughout an idyllic compound of four 1880s houses. On National Register of Historic Places is one of our top local favorites: the 28-unit Cypress House (601 Caroline St.; 305/294-6969 or 800/525-2488; www.cypresshousekw.com) is a distinctive Bahamian-style manse of weathered gray clapboard. Rooms are spacious and impeccable, and one of its social charms is the daily open-bar happy hour poolside (another is owner Dave Taylor's pair of endearing pups, Ben and Gabby). For something a bit larger with more services – not to mention very central, right in the Duval thick of things, the La Concha Crowne Plaza (430 Duval St.; 305/296-2991 or 800/745-2191; www.laconchakeywest.com) dates back to 1926 and is still the tallest building in town; its rooftop bar is a favorite for sunset-watchers.
Among budget options, small and still-shrinking is the pool of lodgings where you can bunk for $100 or less in season, but there are a few standouts. One is the Seashell Motel/Key West Youth Hostel (718 South St.; 305/296-5719; www.keywesthostel.com), lacking a pool but on a quiet street just steps from Higgs Beach. . With a choice of a bed in the clean, air-conditioned communal room or a private room (ten in number, with TV and fridge), it's among the best deals in town. In some ways an even stronger contender is a small, nine-unit compound of clapboard Conch cottages, also on the eastern side of town called Olivia by Duval (511 Olivia St.; 305/296-5169 or 800/413-1978; www.oldtownsuites.com/oliviabyduval). The reason boils down to the property's character: a gracious guesthouse feel and a cute little pool.
Finally, no Key West coverage is complete without mention of the many gay-owned and/or gay-popular lodgings down here, ranging from higher-temperature places catering to men or women only to "all-welcome" guesthouses where you wouldn't hesitate to bring grandma and the kids. One with a classy rep, beautifully landscaped grounds, mixed male-female clientele, and fairly moderate rates is Big Ruby's (409 Applerouth Lane; 305/296-2323 or 800/477-7829; www.bigrubys.com), flagship of a four-property chain extending to Costa Rica and France. If you want to take it all off where the boys are, the Island House (1129 Fleming St.; 305/294-6284 or 800/890-6284; www.islandhousekeywest.com) flaunts an elegant makeover yet still retains a distinctly frisky vibe, with 34 rooms from less than $100 year-round and day passes for non-guests (at the pool and bar/restaurant, there's quite the social scene). For the ladies only, check out the 38-room Pearl's Rainbow (525 United St.; 305/292-1450 or 800/749-6696; www.pearlsrainbow.com), also very tastefully decorated and clothing-optional, for a wide range of budgets but starting at less than $100 nightly.
Where to Stay: Elsewhere in the Keys
There are plenty of lodging options elsewhere in the Keys, from $70/night mom-and-pop motels to large full-service resorts. If your pockets are deep enough, we'd recommend several particularly upscale and well-regarded resorts as well worth an overnight or two (all with excellent spas). Two of the best are Islamorada's classy Cheeca Lodge (81801 Overseas Highway, Mile Marker 82, Islamorada; 800/327-2888; www.cheeca.com) and Hawk's Cay (61 Hawk's Cay Boulevard, Duck Key; 888/443-6393; www.hawkscay.com) on Duck's Key, an elaborate 60-acre resort with its own dolphin program and sailing school. More exclusive and off-the-beaten-path than either is Little Palm Island (28500 Overseas Highway, Little Torch Key; 800/343-8567; www.littlepalmisland.com), a five-acre private island off Little Torch Key with 30 gorgeous bungalow suites, superb service, beachside dining, and adorable miniature (and normally very elusive) Key deer freely roaming the premises.
Hungry? Your choices are legion: some 240 dining spots from simple diner-style joints and old Conch hangouts to cutting-edge kitchens lauded by the world's fanciest bibles of cuisine and travel. On the upscale side, Louie's Backyard (700 Waddell Ave.; 305/294-1061; www.louiesbackyard.com) has been a local favorite since the 1983, with a historic-home setting, fabulous waterfront views, and current chef Doug Shook's blend of Florida, Caribbean, and world cuisine. Though only open since 1999, Alice Weingarten has nonetheless made Alice's Key West Restaurant (1114 Duval St.; 305/292-5733; www.aliceskeywest.com) a local institution with her tropical one-room eatery and inventive fare she has cheerfully dubbed "new world fusion confusion." One of the newest and most appealing dining spots in town is Nine One Five (915 Duval St.; 305/296-0669; www.915duval.com), set in a romantic Victorian manse; sit on the porch and watch the world go by on Duval while nibbling at a superb nouvelle American/international menu built around tapas-style portions (dinner only).
Brunch is big in Key West, and we've got two favorites (both of which also serve excellent lunch and dinner fare, by the way). Blue Heaven (729 Thomas St.; 305/296-8666; www.blueheavenkw.com) is a one-of-a-kind experience set back a couple of blocks from Duval in an area called Bahama Village. A former whorehouse where Ernest Hemingway used to referee boxing matches, it's got an artsy-hippie vibe, live chickens wandering amid the outdoor tables, and a waiting list on most weekend mornings – if you can get a table, order the pecan or fruit pancakes. A little more conventional, but also with a charming hideaway feel, Martin's (416 Appelrouth Lane; 305/296-1183), tucked down a quiet side lane, does German, American, and Continental delectably, and for brunch specializes in several variations on eggs Benedict; opt to sit under the towering ficus on the lovely outdoor deck (at night, it's lit by candlelight and very romantic).
On the more moderately priced side, we urge you not to miss two fairly unique standouts: Pepe’s Café (806 Caroline St.; 305/294-7192), a venerable Conch stalwart, with an old-time vibe (it's been around since 1909), whether you hang out in the leafy brick courtyard or in the rustic boathouse-inspired interior, and great fish sandwiches and the oysters; and the homey El Siboney (900 Catherine St.; 305/296-4184), which dishes up solid Cuban home-cooking – chicken and rice, tangy Cuban-style pork, paella, and island sandwich classics – in an unpretentious diner-like setting (sometimes laid-back, sometimes bustling).
Before we get to more typical Key West nocturnal pursuits, why not consider taking advantage of the high quality offerings of local theaters, including Old Town's Red Barn Theater (319 Duval St.; 305/296-1520; www.redbarntheatre.com) for drama, comedy, and music performances and the Waterfront Playhouse (Mallory Sq.; 305/294-5015; www.waterfrontplayhouse.com) which claims to be the oldest continuously running theater group in Florida and puts on excellent stage performances, including some that will appeal to the kids. The Tennessee Williams Fine Arts Center (5901 College Rd.; 305/296-9911; www.tennesseewilliamstheatre.com) is on Stock Island and worth the 15-minute drive to catch concerts, plays, and performances by the Key West Symphony Orchestra and Key West Pops Orchestra.
For most Key West visitors though, drunkenness calls and drowns out the culture, and Duval Street is where most of the party palaces and inebriation stations are concentrated. Most are open to the street and awash in loud music – imagine a smaller-scale, tropical version of New Orleans' Bourbon Street and that's pretty much lower Duval. By all means, start with the most famous in town, Sloppy Joe's (201 Duval St.; 305/294-5717; www.sloppyjoes.com), made famous as a Hemingway hangout; the cavernous flag-bestrewn room offers up different music acts every night. One caveat: The Sloppy Joe's that Hemingway frequented (and immortalized as "Freddy's Bar" in To Have and To Have Not) isn't actually this one, but a smaller atmospheric joint around the corner now known as Captain Tony's Saloon (428 Greene St.; 305/294-1838; www.capttonyssaloon.com), where Jimmy Buffett got his start; owned since 1958 by Tony Tarracino, a colorful former gambler and mayor, the place is still an excellent pitstop for some local flavor, stuffed as it is with bric-a-brac and a tree growing through its ceiling. Newer watering holes that have achieved a certain notoriety, and following, include Margaritaville Café (500 Duval St.; 305/292-1435; http://margaritaville.com/cafe_KW.php), a touristy restaurant/bar opened by the abovementioned Parrothead-in-Chief and the grittier Hog's Breath Saloon (400 Front St.; 305/292-2032; www.hogsbreath.com), a 1988 offshoot of a Florida panhandle bar whose motto is "Hog's Breath is better than no breath at all." Hard to argue with that logic.
Gay nightlife is a key part of the scene in general, but a few particular spots clustered midway along Duval (around Angela and Petronia Streets) are standouts. The Bourbon Street Pub (724 Duval St.; 305/296-1992; www.bourbonstreetcomplex.com) is a hopping video bar with a small dance floor and quieter courtyard bar and pool. Across the street at 801 (801 Duval St.; 305-296-1992; www.801bourbon.com) you'll find a bar at street level, a popular drag cabaret upstairs, and a slightly more funky/naughty back bar. Newer additions down the street include a small gay men's stripper bar, Kwest (705 Duval St.; 305/292-8500; www.kwestmen.com) and a larger show/video/dance bar called Aqua (711 Duval St.; 305/294-0555; www.aquakeywest.com). Over toward the east side of the island, it's ladies only at Pearl's Patio (525 United St.; 305/292-2032; www.pearlspatio.com), part of Key West's only all-women's bar. The piano bar, low-key outdoor bar, and wonderful if slightly pricey drag cabaret at La Te Da (1125 Duval St.; 305/296-6706; www.lateda.com) is also quite entertaining. Practically de rigueur is the Sunday evening tea dance on the pier at the Atlantic Shores Resort (510 South St.; 305/296-2491; www.atlanticshoresresort.com), which is also a fun place to hang out by day – you can even sun yourself at its clothing-optional pool and quasi-beach.
Cheesy tourist staples and t-shirts have taken over many of the storefronts on lower Duval Street, but there is still plenty of cool, quirky, and intensely local shopping left, especially if you're interested in places selling arts, crafts, and food products. For starters, stop by Duval Street's department-store classic, Fast-Buck Freddie's (500 Duval St.; 305/294-2007; www.fastbuckfreddies.com), which mixes the conventional with the quirky, selling everything from tropical shirts to pink flamingo lawn ornaments. Near Mallory Square at Mel Fisher's Treasure Sales (200 Greene St.; 305/296-2633; www.melfisher.org), the gift shop of the eponymous treasure museum, you can bag both replica and real booty salvaged from the sunken Spanish galleon Atocha. Nearby, the 20 or so shops and kiosks of the two-story Clinton Square Market (291 Front St.) admittedly seem aimed mostly at passengers from the cruise ships docking a few yards away, but can still make for a pleasant and interesting browse. For various and pleasantly scented lotions, soaps, perfumes, and other similar products to keep you in a tropical mood after your vacation is nothing more than a videotape, pop into Key West Aloe (540 Greene St. and 431 Front St.; 305/293-1885; www.keywestaloe.com).
If you like to haunt art galleries, you could spend a week in the dozens of venues here. Top choices include the Gingerbread Square Gallery (1207 Duval St.; 305/296-8900; www.gingerbreadsquaregallery.com); the Key West Art Center (301 Front St.; 305/294-1241); Haitian Art Company ((600 Frances St.; 305/296-8932; www.haitian-art-co.com); Island Arts Co-Op (1128 Duval St.; 305/292-9909; www.island-arts.com); and the Wave Gallery (1100 White St.; 305/293-9428; www.thewavegallery.com). Or how about tropical art to wear instead of hang on the wall? At Key West Handprint Fabric & Fashions (201 Simonton St.; 305/294-9535; www.keywestfashions.com), festive, colorful prints adorn everything from swimsuits to handbags; you can also buy whole fabric to make your own creations. Along the same lines, the cocktail-party and country-club set have worn the creations of Lily Pulitzer for decades; check out her store on Front Street (600 Front Street; 305/295-0995; www.lilypulitzer.com).
For some fairly unique edible and potable mementos, stop in at the Key West Winery (103 Simonton St.; 305/292-1717; www.thekeywestwinery.com) which sells Key lime and mango wines, among others. For goodies – and not just pies – confected from the famous local Key limes, head to the Key Lime Pie Co. (701 Caroline St. & 424 Greene St.; 305/294-6567).
When To Go
High season is mid-December through March, followed closely by the summer months when Key West is flooded with families on vacation. Low season is late summer and early fall – also the height of hurricane season. You'll get the best bang for your buck in late November through early December, plus mild temperatures, low prices, and fewer crowds. April and May can also offer good values, with the exception of spring-break weeks.
However, it's not quite as simple as defining high and low because there are also a number of parties, festivals, competitions, and events that can temporarily turn low season into high and high into super high. Beyond the usual holidays (Memorial Day and Labor Day weekends, Christmas, Fourth of July, etc.), particular ones of note include June's gay Pridefest (www.pridefestkeywest.com); July's Hemingway Days/Lookalike Contest; the Battle of the Bars in August; September's Womenfest; the huge blowout Fantasy Fest in October; and November's Parrotheads in Paradise. For other events, check the local chamber of commerce online events calendar (www.wliinc3.com).
Mid-December through March
Late August through Mid-October
Best bang for your buck
November through early December
Key West International Airport (EYW) receives direct flights on American (www.aa.com) from Miami; on Cape Air (www.flycapeair.com) from Naples and Fort Myers; on Continental (www.continental.com) from Fort Lauderdale, Fort Myers, Gainesville, Jacksonville, Miami, Orlando, Tallahassee, and Tampa/St. Petersburg; on Delta (www.delta.com) from Asheville, Atlanta, Birmingham, Milwaukee, Minneapolis, New York, Norfolk, and Orlando; on Florida Coastal Airlines (www.flyfca.com) from Fort Lauderdale; and on US Airways (www.usairways.com) from Fort Lauderdale, Orlando, and Washington/National.
Flying in to Key West is generally pricier than catching a flight into Miami (MIA) or Fort Lauderdale (FLL) and then getting a bus or van connection or renting a car, and in fact more than 80 percent of arrivals are by road. You can book said connection from Miami airport on Keys Shuttle (888/765-9997, 305/289-9997) and Greyhound (800/410-5397; www.greyhound.com). If you opt to drive down, both I-95 (in Miami) and the Florida Turnpike (in Florida City) connect with U.S. 1, which runs south through the Keys and ends about 3.5 hours later in Key West. It's a mostly scenic drive, with lots of over-water causeways. There's currently no Amtrak service.