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The Perfect Weekend in Key West

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Key West's relatively small, compact size makes it easy to explore if you've only got three days, either by foot or try the hop-on-hop-off trolley. Don't miss Ernest Hemingway's House, the buoy marking the U.S.' southernmost point, and shopping the boutiques and art galleries on Duval Street. And at the end of the day, follow the crowd to Mallory Square to watch the sunset.
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601 Front St, Key West, FL 33040, USA
Key West’s small downtown is undergoing a renaissance of sorts, perhaps best characterized by The Marker, a new hotel opening in early 2015 that straddles the line between iconic and forward-thinking.
 
The wrapping is classic Key...
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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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400 Front St, Key West, FL 33040, USA
The Hog's Breath Saloon on the corner of Duval and Front Street in the heart of Old Key West has been in business since 1988. The Saloon was a hit from the day it opened. It's a place to enjoy lunch or relax after a day of swimming, fishing, or...
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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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1435 Simonton St, Key West, FL 33040, USA
You can enjoy a romantic dinner at a table set up on the beach at Spencer’s by the Sea, the upscale steakhouse at The Reach, A Waldorf Astoria Resort. (You can also eat on a less sandy deck over the beach or in the dining room.)...
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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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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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3101 N Roosevelt Blvd, Key West, FL 33040, USA
Opened to celebrate Florida's healthy way of life, the Eco Bar is the only bar on the island to serve sustainable cocktails, wine, and craft beers. Chris Holland, who owns the Stoned Crab, is passionate about keeping things green....
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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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1500 Reynolds St, Key West, FL 33040, USA
Key West doesn’t have many swimmable beaches, but this elegant 1920 oceanfront resort sits on the largest private one in town—an 1,100-square-foot strand punctuated with tall palms. While the shoreline itself is on a rocky shelf, a...
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938 Whitehead St, Key West, FL 33040, USA
The U.S. Navy opened the Key West lighthouse in 1848 to help commercial and military vessels navigate the coral reefs around the harbor. After decommissioning, the lighthouse and the house in which its keeper lived were converted into a museum....
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1075 Duval St, Key West, FL 33040, USA
Ocean Grill & Bar is the locals' choice for special occasions. While the mood is relaxed (it's still Key West, after all), the cuisine hits all the right notes for a big night or brunch out. The generously wide porch is set with tables...