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Key West

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907 Whitehead St, Key West, FL 33040, USA

Key West’s most famous literary resident, Ernest Hemingway, lived in this two-story Spanish-colonial villa for nearly a decade and composed several of his best-known works here. His second wife, Pauline, insisted they add a pool to the...

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202 William St, Key West, FL 33040, USA

Take your pick of schooners, catamarans, even a pirate ship—any one you choose will get you out on the water, one of the best ways to experience a Key West sunset. Most tours leave from the harbor at Key West Bight and sail south to the tip...

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Florida, USA
Set 110 kilometers (70 miles) south of Key West is a group of seven uninhabited islands known as the Dry Tortugas, which makes for one of the area’s top day trips. Once there you can explore the historic Fort Jefferson, an enormous military...
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220 Simonton St, Key West, FL 33040, USA

New Orleans may be home to America’s most festive thoroughfare, Bourbon Street, but Key West’s Duval Street is a close second. This two-kilometer-long (1.25-mile-long) road runs from north to south, from one end of the island to the...

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601 Howard England Way, Key West, FL 33040, USA
Yes, there is a fort here—a National Historic Landmark built in the mid-1800s to protect the country’s southernmost coastline—but locals know it for its excellent beach. A nice sandy expanse is a rarity in the Florida...
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Whitehead St & South Street, Key West, FL 33040, USA
The Southernmost Point buoy, at the corner of Whitehead Street and South Street, marks not only the spot for the southernmost point of the continental United States but also the distance (90 miles) to the next country, Cuba. The...
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303 Front St, Key West, FL 33040, USA

Get an overview of the most important historical sites in Key West’s Old Town district on this narrated 1.5-hour-long ride, which is technically not on a train but on a brightly colored train-shaped shuttle. It starts at Front Street and...

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400 Wall St, Key West, FL 33040, USA

Key West is billed as "the Home of the Sunset," which means every time the sun sinks below the horizon, it’s time for a party. Since the 1960s, Mallory Square’s dock has been hosting this nightly celebration, which begins two hours...

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200 Greene St, Key West, FL 33040, USA

This museum showcases treasures from 17th- and 18th-century European and English shipwrecks discovered in the waters around Key West. Artifacts include navigational instruments, armaments, silver and gold ingots, cannons and shackles from slave...

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Pigeon Key, Florida, USA

Not to be confused with the modern bridge that runs parallel to it, the Old Seven Mile Bridge was originally part of the Overseas Railroad built in the early 20th century by Henry Flagler. It began allowing automobiles in 1938, but after being hit...

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420 Eaton St, Key West, FL 33040, USA

Expect exotic flavors—and long queues—at this gourmet donut shop in the heart of Old Town. Along with the usual—vanilla, jelly-filled—look for hibiscus, blood orange and Key lime donuts.

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245 Front St, Key West, FL 33040, USA
Latitudes is the acclaimed restaurant at the Sunset Key Cottages, on Sunset Key, a small private island accessible only by boat. Take the ferry across the Key West Harbor—your scheduled ferry time is your reservation time. The dreamy...
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429 Caroline St, Key West, FL 33040, USA
In the land of piña coladas and light beers, The Other Side cocktail lounge is chiseling out new booze territory one ice globe at a time. Drinks, loosely inspired by the Keys, are like nothing else on the island. There’s the frothy...
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806 Caroline St, Key West, FL 33040, USA

Old-school Key West at its best—this steak house and seafood spot near the waterfront has been around since 1909. The fun, funky atmosphere with lots of wood and a mishmash of nautical memorabilia has a laid-back vibe, and you can dine...

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201 Duval St, Key West, FL 33040, USA

No place is quite as synonymous with the Key West spirit as Sloppy Joe’s, which has been around since 1933 and was a regular hangout for Ernest Hemingway; the bar even hosts an annual Papa look-alike contest, with white-bearded men competing...

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602 Greene St, Key West, FL 33040, USA
Voted the #1 shop in Key West on Trip Advisor Peppers has hundreds of different hot sauces to take home as the ultimate Key West souvenir. Ranging in heat from mild to 'weapons grade' there is a flavor suited to anyone who loves to use this...
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113 Fitzpatrick St, Key West, FL 33040, USA

Founded in 1984, this is the oldest cigar factory operating in the Keys, and it uses traditional Cuban methods to cure and roll its stogies. You can choose from a large selection of cigars and also watch a skilled torcedor (cigar roller) in...

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1207 Duval St, Key West, FL 33040, USA

The oldest gallery in Key West, Gingerbread Square is housed in a historic building and features paintings, limited-edition prints, glassware, ceramics and sculptures crafted by noted artists, many of them local.

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1 Whitehead St, Key West, FL 33040, USA

Set in a former icehouse in the Mallory Square shopping area, this store stocks shells galore (ones found in the Keys and others from around the world), as well as jewelry made from shells, coral and shark's teeth. There are also sea-themed home...