Overview

Key West, Florida, is a haven for the famous, the nonfamous and for those looking to get a little lost. Everyone seems to enjoy Key West's relaxed pace, storybook architecture, colorful history, live-and-let-live local attitude and end-of-the-world feel.

The natural surroundings in Key West are just as pleasant: Hibiscus, bougainvillea, palm trees and other flora and fauna give the island a tropical feel and smell.

And when the sun begins to set each day, there's cause for celebration in Key West as street performers, arts-and-crafts vendors and other characters participate in the waterfront activities at Mallory Square.

Venture off the island for snorkeling, diving or fishing. Or you can just walk around Old Town and soak up the mix of flavors, including hints of Cuba and Old Florida.

But no matter how you spend your time in Key West, expect to be part of a crowd, because Cayo Hueso, as the Cuban locals call it, draws droves of visitors, many of whom wish they could become locals, if not genuine conchs (that's Key West-talk for island natives).

Note: Key West sustained serious damage during Hurricane Irma in September 2017. Recovery efforts will take months or even years. Travelers should investigate current conditions prior to planning a visit.

Geography

The tiny island (2 mi/3 km wide by 4 mi/6 km long) is one of about 1,000 coral islets in the Florida Keys, an archipelago that stretches 126 mi/203 km southward from the tip of mainland Florida. U.S. Highway 1, also known as the Overseas Highway (it spans the East Coast and straddles the Gulf of Mexico and Atlantic Ocean in the Keys), links Key West to the rest of the state. The roadway ribbons its way across 34 of the islands that form the Florida Keys and over 43 connecting bridges, including one that's a spectacular 7 mi/11 km long.

Because Key West is small and a snap to navigate, you can easily explore most of it on foot (or, better yet, on bicycle). The main sights are concentrated in Old Town, on the western side of the island. Duval Street is the main thoroughfare, packed with bars, souvenir shops and bed-and-breakfasts. Off Duval, Old Town's streets are lined with picket fences and Victorian-era frame houses decorated with gingerbread trim.

History

The U.S. government acquired Key West from Spain in 1819 as part of the Florida Purchase, and back in those days, pirates were active in the area. After the U.S. Navy put the pirates out of business, most of the isolated islanders made lucrative livings as wreckers, salvaging the booty from ships that wrecked on the coral reefs offshore. In fact, between 1828 and the 1850s, Key West was considered the richest city, per capita, in the United States.

That business waned in the mid-1800s after the government built lighthouses, so the islanders turned to shrimping, fishing, sponging and cigar making—with the help of Cuban dissidents who had fled their island and Spanish rule. John James Audubon visited Key West and the Dry Tortugas in 1832, but for the most part, the islands were unknown to outsiders. During the Spanish-American War and World War I, major military installations were built on Key West, but much of the local economic base began to fade in the 1920s as the military left and the cigar industry moved northward to Tampa.

After the Depression, the city began to bill itself as a tourist destination, advertising its weather, architecture and lifestyle. Artists and writers flocked there; notable 20th-century visitors included writers Tennessee Williams, Elizabeth Bishop and Ernest Hemingway, as well as U.S. President Harry S. Truman.

In 1982, Key West residents declared it tongue-in-cheek as the Conch Republic, as a means of attracting attention to local concerns they felt the Florida legislature was ignoring, and—quite intentionally—brilliantly used the attention to showcase Key West as a quirky tourist destination .

Today, tourism remains the mainstay of the local economy—each year this city of slightly more than 25,000 permanent residents draws hundreds of thousands of visitors, who arrive by plane, car and cruise ship.

Sightseeing

Key West is small enough that you'll need little more than a comfortable pair of walking shoes (or perhaps a bike) to take in most everything the city has to offer. To start, you may want to get the lay of the land by hopping on the Conch Tour Train or the Old Town Trolley—both will take you past virtually every point of interest on the island. (The Conch Train is nonstop, and the Trolley has 13 hop-on/hop-off points.)

Most of the sights are located in Old Town, where you'll find charming bed-and-breakfasts and Victorian houses with gingerbread trim mingling with packed bars and countless souvenir shops. The main drag, Duval Street, is crammed with restaurants, bars, galleries and shops. The Duval Crawl is a popular phrase used to describe evening explorations up and down the island's main street to sample many taverns and entertainment venues. Duval is a good landmark to use for figuring out where you are and where you're going. The southeastern end of Duval is near the Southernmost Point in the continental U.S. (a requisite photo op for all visitors).

From there, you can stroll north on Whitehead Street, passing several popular attractions. These include the Ernest Hemingway Home and Museum and the Key West Lighthouse. Farther north are the historic Audubon House and Tropical Gardens, Harry Truman's Little White House Museum, and the Mel Fisher Museum (filled with gold artifacts recovered by the underwater treasure hunter).

Head a few blocks east of Duval to explore the Key West Cemetery; the often-irreverent inscriptions on this must-see collection of aboveground graves capture the island's quirky character. At the far-northern end of Whitehead, you'll find Mallory Square, home of the not-to-be-missed nightly Sunset Celebration. Or, for a less-hectic sunset experience, order a cold, fruity drink and relax at an outdoor bar at waterside. Nearby White Street features an array of art galleries.

Nightlife

Although proud of its party-town reputation, Key West parties flip-flop style—casual more than crazed—and the rum drinks are sipped at outdoor bars rather than in neon-striped nightclubs. The party often starts on sunset catamaran cruises and continues into the early-morning hours.

Along Duval Street, there's lots of live music: sometimes full bands playing rock, jazz and reggae, but more often solo guitar strummers and singers cast in the mold of Key West's strummer-made-good, Jimmy Buffett. (According to our research, you can't spend more than 27 minutes in any Key West bar before hearing a Jimmy Buffett song.)

A night out in Key West can last until 4 am at bars and clubs that cater to a late-night crowd. On the flip side, partiers always have the option of starting their fun early—say, about 9 or 10 in the morning.

Remember to not drink and drive—on land or on sea.

Dining

For such a small island, Key West has more than its fair share of quality restaurants. Foodies can delight in the choices, while those who just don't care will be very happy with the easy options.

Seafood, not surprisingly, is the mainstay in Key West, and much of it is fresh from nearby waters. Florida lobster and stone crabs are good choices, as is conch, a chewy shellfish best served in soups or in fritters (deep-fried in a spicy batter). Many of the restaurants have been influenced by flavors from Cuba and other parts of the Caribbean and serve what is known as Floribbean-style cuisine. For dessert, try—what else?—key lime pie, which has a tart yellow (not green) custard filling and a graham-cracker crust.

General dining times are 6:30-10:30 am for breakfast, 11 am-2 pm for lunch and 6-10 pm for dinner. Many bars and restaurants in Old Town serve food until the wee hours of the morning.

Expect to pay within these guidelines for a meal for one, not including drinks, tax or tip: $ = less than US$15; $$ = $15-$25; $$$ = US$26-$40; and $$$$ = more than US$40.

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