Kicking Back in Key West

Follow our guide to the best food and fun in this quirky little town made famous by the likes of Buffett and Hemingway.

Key West Southernmost Point

Photographer Jennifer Davick

Land's End

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.)

Contemporary Key West

Photographer Laura Davick

Local Buzz

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 67 bars along Duval Street or joining the throngs that celebrate sunset each night on the town wharf.

So whether you feel like fine 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.

Key West's My Blue Heaven

Photographer Laura Davick

Smart Start

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.

Key West Shopping

Photographer Laura Davick

Keys to Home

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), Key West Art Bar (901 Caroline Street; 305/296-0424 or keywestartbar.com), and 7 Artists (604 Duval Street; 305/293-0411 or 7artistskeywest.com). And don’t miss Fast Buck Freddie’s (500 Duval Street; 305/294-2007 or fastbuckfreddies.com). Even a beer-deprived husband will get a kick out of the whimsical housewares and tropical-print clothes.

Key West Tour

Photographer Laura Davick

Road Trip

Catch a ride on the Conch Tour Train ($29 adults, $14 ages 4–12, discounts for online purchases; 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).

Key West's Hogfish Bar and Grill

Photographer Laura Davick

Tropical Fare

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

Hemingway's Home on Key West

Photographer Laura Davick

Hometown Hero

No visit to Key West is complete without a tour of author Ernest “Papa” Hemingway’s home ($12 adults, $6 ages 6–17; 305/294-1136 or hemingwayhome.com), where he penned For Whom the Bell Tolls and Death in the Afternoon. 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.

Key West's Smathers Beach

Photographer Laura Davick

On the Water

On Key West’s nicest 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 ($40–$50; 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.

Key West Spa Treatments

Photographer Laura Davick

Taking It Easy

Luxuriate with a beachfront massage or other signature treatment at Casa Marina Resort (from $179; 888/303-5717). Or try a chocolate chip sugar body scrub at Pier House’s Caribbean Spa (from $249; 800/723-2791 or pierhouse.com).

Key West Mallory Square

Photographer Laura Davick

Sinking Feeling

Every day slips into the shadows with a celebration of sunset. 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 reddish orb slide into the sea.

Key West Sunset

Laura Davick

Sun Catcher

Waterborne option: Take a sunset sailing trip aboard a catamaran ($37 adults, including beer, wine, and sodas, $18.50 ages 6–12, discounts for online purchases; 877/994-8898 or furycat.com).

Key West Fine Dining

Photographer Laura Davick

Memorable Feast

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

Key West drinks and music

Photographer Laura Davick

Only in Key West

Margaritaville is more than a song. In Key West, it’s the quintessential state of being, and no evening is complete with a stop for a drink and tunes. For rowdiness, head for Sloppy Joe’s (201 Duval Street; sloppyjoes.com). One of Papa’s favorite watering holes, the 158-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.

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.

Originally published September 2009

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