The self-proclaimed "Conch Republic" is one of Florida's most unique and colorful escapes, with a long and fascinating history to match. Here's where to eat, drink, play, and stay in the land of Buffett and Hemingway.
In Key West, every day is an excuse for a good time. Its location seems to encourage the anything-goes attitude that pervades this leafy little town. Whether you fly here over the indigo-and-teal waterscape of reefs and islands or drive the 127-mile Overseas Highway, you’ll get the picture: Key West is the end of the American road.
Built in the 1800s on wealth salvaged from shipwrecks, Key West has always been a self-reliant renegade. When the U.S. Border Patrol blockaded the Keys’ access road to limit illegal immigrants and drugs in 1982, Key West seceded from the nation, dubbed itself the “Conch Republic,’’ and petitioned the federal government for foreign aid. (The blockade quickly dissolved.)
In the past few years, Key West has done some growing up, and its insouciance has been tamed―today’s hot debates center around the roosters that wander about town. But you can still soak in the town’s irreverent spirit by hopping on a scooter and wheeling over to one of the myriad bars along Duval Street or joining the throngs that celebrate sunset each night on the town wharf.
So whether you feel like fashion-forward dining, getting a cultural fix at The Ernest Hemingway Home & Museum, or shopping for art, here’s our guide for making the most of a weekend in Key West.
A cat sleeps on the bar, a crowing rooster ambles across the yard, and the irresistible scent of fresh-baked pineapple pancakes wafts across the palm-sheltered courtyard. You’re at Blue Heaven (729 Thomas Street; 305-296-8666 or blueheavenkw.com), the spot for Key West’s best breakfast.
Created by an artist and writer―his brother, a professional chef, has taken over the kitchen―Blue Heaven offers yummy eats inspired by local ingredients. (Don’t miss the silky shrimp-and-grits.) The casual historic house once hosted cockfights, gambling, and boxing matches refereed by Papa himself.
Whether you’re on the hunt for a Hard Rock T-shirt, a Coach bag, or a pink flamingo punchbowl, you’ll want to carve out time for a leisurely stroll down Key West’s main drag, Duval Street. Sure, it has its share of souvenir stalls, but you’ll also find good local artwork as well as crafts and clothing from around the globe.
Be sure to stop in Gallery Key West (824 Duval Street; 305-292-0046) and 7 Artists (604 Duval Street; 305-293-0411). And don’t miss Fast Buck Freddie’s (500 Duval Street; 305-294-2007). Even a beer-deprived husband will get a kick out of the whimsical housewares and tropical-print clothes.
It's touristy and totally worth it: Catch a ride on the Conch Tour Train (800-868-7482 or conchtourtrain.com). Since it first starting giving tours in 1958, the train has offered insights―mostly true―into Key West’s past.
As you roll past blazing bougainvillea cloaking gracious clapboard houses, you’ll learn about the Overseas Railway (completed in 1912 at a cost of $30 million), the sponge trade (destroyed by a 1939 blight), and former Mayor Sonny McCoy’s 1978 feat (waterskiing all the way to Havana).
Refuel at an airy seafood joint where the breeze blows straight in from the water and your food comes in plastic or paper but never china. Choices include the historic Turtle Kraals (231 Margaret Street; 305-294-2640 or turtlekraals.com), once home to corrals for soon-to-be-souped turtles. Now the turtle-free menu features barbecue.
Or hit the Half Shell Raw Bar (231 Margaret Street, 305-294-7496, halfshellrawbar.com) at the old seaport, called the Bight, or the nearby Conch Republic Seafood Company (631 Greene Street; 305-294-4403 or conchrepublicseafood.com). Our fave: hogfish, caught only with a spear and served grilled at its namesake Hogfish Bar and Grill (6810 Front Street, Stock Island, 305-293-4041 or hogfishbar.com) on Stock Island, a short drive away.
Left: Lobster and shrimp pot pie at Hogfish Bar and Grill
No visit to Key West is complete without a tour of author Ernest “Papa” Hemingway’s home (305-294-1136 or hemingwayhome.com), where he wrote For Whom the Bell Tolls and Death in the Afternoon. (Don't miss spotting Hemingway's manual typewriter, on display in his writing studio in a tiny outbuildling linked to the house by a catwalk.) And speaking of cats, visitors come as much for the 50 descendents of the author’s own six-toed felines as the tales of Hemingway’s philandering, drinking, and literary habits.
On Key West’s nicest public stretch of shoreline, Smathers Beach, you can try your hand at kayaking and windsurfing or just spend some time in the sand. But we suggest signing up for a snorkeling excursion (877-994-8898 or furycat.com and 800-507-9955 or keywestsebago.com) to Sand Key reef, with shallow waters, a lighthouse, and endless schools of glimmering fish.
One of the best stays on Key West is the beautifully restored and historic Waldorf Astoria Casa Marina (305-296-3535 or casamarinaresort.com), and its beachfront Spa Al Mare is perfection (the Ocean Breeze Massage may become your daily ritual). The scrubs at Pier House’s Caribbean Spa (800-723-2791 or pierhouse.com) are another local indulgence worth booking.
Every day slips into the shadows with a celebration of sunset as only Key West can do it. Jugglers, tightrope walkers, fire-eaters, and craftspeople gather each evening on the dock at Mallory Square. This is your chance to pick up a hibiscus-patterned collar for Fifi, an agate-and-shell nightlight, or playful Island Time yard sign as you watch the sun slide into the sea. Can you catch the storied "green flash" that occurs right when the sun dips below the horizon? It's a Key West tradition to try.
While hanging out in Mallory Square is a party any and every night, there's nothing more romantic than a Keys sunset from the deck of a boat. Capture that romance aboard a catamaran from Fury Water Adventures, and don't overlook the beer and wine included with your purchase price. For music fans, The Live Music Sunset Cruises are a total blast (877-994-8898 or furycat.com).
Key West’s top restaurants reach far beyond fried shrimp and burgers. You’ll do best to look for a menu featuring both imported ingredients and local seafood. Try Nine One Five (915 Duval Street; 305-296-0669 or 915duval.com), Key West’s best gourmet option, featuring award-winning fusion preparations like clams with imported chorizo. If the weather’s good, aim for a table on the porch.
Or visit Café Marquesa (600 Fleming Street; 305-292-1244 or marquesa.com), part of the casual yet elegant Marquesa Hotel. Menu items emphasize local ingredients; the macadamia-crusted yellowtail is sure to please.
Left: Nine One Five
Margaritaville is more than a song. In Key West, it’s a state of mind, and no evening is complete with a stop for a drink and tunes (or several). For rowdiness, head for Sloppy Joe’s (201 Duval Street; sloppyjoes.com), which is open 365 days a year, from 9 a.m. to 4 a.m. (except for Sunday, when you've got to wait until noon). One of Papa’s favorite watering holes (and the 165-year-old location of the original Sloppy Joe’s) is now Capt. Tony’s Saloon (428 Greene Street; 305-294-1838 or capttonyssaloon.com), cozier and― sometimes―less boisterous.
Don't miss the Green Parrot Bar (601 Whitehead Street; 305-294-6133 or www.greenparrot.com), another classic joint where the music just seems to spill out onto the narrow sidewalk, and for a nightcap and classic rock, hit the Hog’s Breath Saloon (400 Front Street, 305-296-4222 or hogsbreath.com). Somewhere along the way, you’re sure to hear the Jimmy Buffett anthem.