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Key West, Florida

Key West. Just the name of America’s tropical island-city makes many boaters yearn to shuck their mainland shackles and cruise south — for racing, fishing or just hanging out.

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If you do, you’ll be following the 1820s Connecticut fishermen who sailed here to fish all winter for the lucrative Havana market.

Although you can drive to Key West — at the end of Route 1 — it’s really a state of mind, and arriving by boat gives you time to adjust to the uniqueness. Dockage can be reserved at city marinas, eight private marinas downtown, at the Historic Seaport or neighboring Stock Island, or yachts can anchor out. The city’s Key West Bight Marina — (305) 809-3984 — rents slips and offers dinghy dockage for boats anchored across the channel. Key West City Marina — (305) 809-3981 — rents dockage in Garrison Bight and moorings. Once ashore, walk or bicycle to avoid traffic and parking hassles.

Key West’s infamous end-of-the-road, devil-may-care reputation might tempt you to spend all your shore time sampling the 200-plus bars and restaurants on this 2-by-4-mile island. And some do, beginning with Schooner Wharf’s 7 a.m. happy hour and ending at 4 a.m., when bands stop and bars close. Capt. Tony’s and Sloppy Joe’s — Ernest Hemingway’s haunts — along with the Green Parrot, Schooner Wharf, Hog’s Breath, Margaritaville and others line Duval Street and the Historic Seaport, the former commercial fishing harbor and red-light district.

But Key West isn’t just another tropical paradise. It’s a mix of New Orleans’ French Quarter, Havana, Greenwich Village and New England moving to a Caribbean beat with the exuberance of a college town after a division championship. Explore its flamboyant 200-year past and you’ll find its funky, trendy, historic and diverse ethnic elements clashing, competing and blending into an increasingly gentrified, touristy present. Everything’s bathed in brilliant sunshine and overrun with tropical foliage.

After Alabama businessman John Simonton bought pirate-frequented Cayo Hueso (Spanish for “island of bones”) in 1822 for $2,000, the U.S. Navy routed local pirates and established a base here at the “Gibraltar of the West.” Bahamians, New Englanders, Cubans, adventurers, Africans, military personnel and shipwreck victims settled here.

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By the mid-1800s — decades before Miami was incorporated — sharpies, schooners and steamboats linked Key West with its cultural and economic peers: New York, New Orleans, Havana and Charleston, S.C. Key West was Florida’s largest and richest city per capita, home to the state’s first millionaire. His ship chandlery served neighbors who salvaged vessels wrecked on the reef — an honorable profession. Key West is believed to be the only city in the world that issued federal salvage licenses. For almost 100 years, the U.S. District Court in the Customs House distributed profits from auctioned cargoes among ship owners, the wreck master and other salvors.

Lighthouses ended that prosperity. Fishing, turtling, sponging and cigar-making boomed and busted, leaving Key West bankrupt in 1933. The 1935 hurricane destroyed Henry Flagler’s engineering marvel, the “Railroad that Went to Sea,” which opened in 1912. Completion of the Overseas Highway in 1938, the Navy, World War II and subsequent tourism revived the city.

My favorite activity is strolling the byways in Old Town, a National Historic District of some 3,100 homes, churches and commercial buildings. Side by side sit renovated classic Greek Revival homes with two-story porches, opulent Victorian mansions, cigar makers’ “shotgun” cottages and simple wooden homes pegged together by shipwrights. Louvered shutters and more than 50 varieties of intricate gingerbread decorate all but the earliest homes. Ornate fences often enclose cool, shady gardens of murmuring fountains and the flamboyant flowers I recall from South Pacific islands, which flourish in Key West’s climate. The majority of buildings date from 1886, when fire destroyed most of the city as the lone fire engine was being repaired in New York City.

Ernest Hemingway’s home, of course, draws crowds. The walking map also marks the homes of Tennessee Williams, Robert Frost, eight other Pulitzer Prize winners and scores of other famous residents, including John James Audubon, President Harry Truman and singer-songwriter Jimmy Buffett.

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Guided walking tours can’t compare with the funky Conch Tour Train, which winds through Old Town. The trolley tour also includes the shopping centers and Atlantic beaches of the island’s dredged and filled northern side.

The above-ground cemetery, sculpture garden and two dozen museums, including three Civil War masonry forts that kept Confederate-sympathetic Key West in Union hands, explain every facet of Key West’s history, geography, and flora and fauna. Mel Fisher’s Maritime Heritage Museum displays mind-boggling salvaged Spanish treasure. Don’t miss the Key West Butterfly and Nature Conservancy, an oasis of calm and serenity.

Key West adapts to its diverse visitors with activities — ghost tours and pub crawls, Fantasy Fest and Conch Republic Independence Days, parasailing and sky diving, fishing charters and biplane rides — and culture — the annual Key West Literary Seminar, whimsical outdoor sculpture, theater, music, galleries and upscale boutiques in Bahama Village, along White Street and Upper Duval. The concession-dotted 2-mile stretch of free public Atlantic beaches lures tourists, but locals prefer Fort Zachary State Park’s sands.

Don’t miss the sunset celebration on Mallory Square and Dock. With a conch fritter and a libation, take in the spectacle — musicians, jugglers, fortune tellers, buskers and crafts vendors, with sightseeing sailboats crisscrossing the harbor. Toss some cash into the waiting hats, then cheer as the sun sinks beneath the sea. And watch for the elusive green flash. (The Westin Resort, Pier House and Ocean Key Resort have quieter waterfront tables. White Street Pier offers only the sunset.)

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Scores of highly rated restaurants serve excellent cuisine, from continental to Cuban, seafood to sushi. We prefer the Old Key West ambience and lower prices at Pepe’s (any meal), El Siboney (Cuban), Courthouse Deli (sandwiches) and Blue Heaven (breakfast with the roosters). Fausto’s Food Palace is the lone supermarket among downtown’s many takeout stands, ice cream shops and convenience stores. Pepe’s Restaurant and others sell package goods.

The Southern Ocean Racing Conference’s annual Fort Lauderdale to Key West Race, Quantum Key West Race Week (119 boats in 2012) and Key West Super Boat World Championships attract Olympic medalists and international competitors.

Whether you come by car, plane or yacht, who can resist year-round boating in shorts and T-shirts, with camaraderie ashore on every corner? And after a hard day of racing or a hard night of partying, when you breathe in that soft tropical air, it’s hard to believe you’re still in the United States.

See related articles:

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- Stonington, Conn.

- St. Marys, Ga.

- Rockland, Maine

This article originally appeared in the August 2012 issue.