Last updated: 11:00 PM ET, Sun July 03 2016

All-Stars of Key West’s Dining Scene

Destination & Tourism | Charu Suri | July 03, 2016

All-Stars of Key West’s Dining Scene

PHOTO: A rum flight at RUMba. (photo courtesy of the Waldorf Casa Marina Key West) 

The southernmost city in the United States has a party town reputation, with a history of rum runners, bed races (as part of the town’s annual “Fantasy Fest”) and the chance to watch some of the most spectacular sunsets.

But along with its relaxed vibe and literary history (the area was home to Ernest Hemingway, Tennessee Williams, James Merrill and Elizabeth Bishop, among others) is a noteworthy drink and dining scene that include newcomers sidling with tried and true staples.


This lobby bar, located at the mansion-style Waldorf Astoria’s Casa Marina, has an elaborate array of rums that are a nod to the region’s bootlegging history. No pirate will serve you, but you can slake your thirst by going for Dark & Stormies made with Bermuda-based Gosling’s rum, or indulge your curiosity by going for flights that include a 21-year-aged Appleton rum and even a citrusy 40-year-aged Pyrat Cask rarity that can set you back $470 a bottle. The latter is as mellow as a summer’s day.

READ MORE: The Florida Keys Are a Tropical Paradise

RUMba doesn’t allow you to forget that you are only 90 miles away from Cuba: you’ll be wise to relax on the patio with a cigar fashioned by the Rodriguez Cigar Factory, the oldest operating cigar manufacturer in the Florida Keys, and take in a poetic sunset or two.

Phone: 305-296-3535

Blue Heaven

This Key West institution is hip with history, and even housed a boxing ring where Hemingway used to referee matches. Now, it is a lush place to dine in the island’s historic Bahama Village, with a rustic-looking stage for nightly live entertainment, and an authentic menu with a key lime pie that is arguably the largest slice on the island (and made from scratch).

Owners Suanne and Richard Hatch are island free spirits, and the restaurant mirrors their personalities. You’ll find chickens and cats roaming the premises as well as a truly laid-back vibe and the feeling that you are dining hodge-podge style in a family’s hospitable backyard. But the food is truly home-style and delicious: blueberry pancakes, carrot and curry soup, baked meringue and scallops all dance their way to the table.

Phone: 305-296-8666; open seven days a week.


This restaurant, part of the Westin Resort at Sunset Key, is only accessible by boat, with ferries departing the harbor every half hour. But it is such a special affair, because you will see sunsets just as Tennessee Williams would have wanted it, with his “see you at sunset” mantra with gin and tonics in hand, or Audubon’s glowing memories. 

With views of the Gulf of Mexico, guests can dine on Caribbean-style cuisine that includes the popular seafood pasta (“made from scratch,” the chef tells me) to the Lobster fondue. There is plenty of seating on the key’s private beach strip as well as its airy interiors, but you would be wise to make reservations at this popular spot.

Phone: 305-292-5394

Sloppy Joe’s

The bar synonymous with Key West was infamous long before it was famous.

It was a saloon that defied Prohibition and was serving whiskies and gins for dimes during the 1930s. This was one of the few places in Florida where one could get a good drink, and of course Hemingway frequented it and became firm friends with owner Joe Russell himself. But it wasn’t exactly a refined place, and became known as the “Silver Slipper” for a brief time with the addition of a dance floor.

READ MORE: Key West Port Guide: 9 Attractions to Check Out

But the Sloppy Joe’s name and vibe stuck, through the years, even though the facade and interiors morphed from a saloon to a sports bar. Go there for the snacks, the rum and dress like Papa Hemingway during the Look Alike contest and be a true local.

Phone: 305-294-5717

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