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.
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.)
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.
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.
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.
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).
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
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
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