Attractions
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.
Day Sails
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).
DAY TRIPS
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.
Miami/Miami Beach
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.
$279+: 5-nt exotic cruise to Western Caribbean ports from FL Royal Caribbean
$125+: Key West, Cococay & Nassau 4-nt cruise from Miami Royal Caribbean
$349+: Caribbean & Cancun 7-night cruise on MSC Poesia MSC
76% off Caribbean and Bahamas Cruises from Baltimore Editors' Review
$334+: Cheap 7-nt winter cruise to Western Caribbean cities Cruise.com
$334+: 7-nt Montego Bay & Key West cruise, kids sail free Cruise.com
$164+: Bahamas 4-nt cruises with $25 onboard ship credit Royal Caribbean
$149/nt+: Key West beachfront hotel w/4th nt free & champagne Perfect Escapes
$109/nt+: Key West hotel w/pool & 2 restaurants Travelocity