Key West

48 Hours: Key West

This southernmost city in the United States has a way of achieving notoriety. Take the time it “seceded” to become the Conch Republic. Or José Martí’s historic attempts to galvanize exiled Cubans. Then there’s the renowned Fantasy Fest, an annual jaunt that empties stores across the nation of glitter, body paint, and dubious costumes! Now, we’re not promising that much infamy in a single go, but follow these recommendations and you can certainly regale others with stunning tales from your trip to Key West.

Key West For Foodies

If it’s Sunday, taxi over to Matt’s Stock Island Kitchen and Bar for buffet mastery. Sample some of the thickest bacon on the island, a raw bar, and unlimited small plates in addition to all the delicious staples of a superb breakfast spread.

Stay downtown and nestle into the intimate courtyard and wild Frida Kahlo decor at Frita’s Cuban Burger Cafe located at 425 Southard St. Owner Marcia Weaver offers up her popular Frita Burgers and extraordinary pork tacos.

Similarly, The Castellano Brothers at Blackfin Bistro never disappoint with their Wagyu Burger, decadent goat cheese croquettes, and rich Carbonara in their minimalist chic setting right on Duval for lunch and dinner.

Later, retro supper club vibes meet fine dining at the quirky Flaming Buoy Filet Co., hosted by witty proprietors Fred Isch and “Scot” Forste. Tucked away at 424 Eaton St., reservations are recommended to try their Lobster Macaroni & Cheese, Filet Mignon Flatbread, and Bacon Wrapped Scallops. As a bonus, try to spot all the science fiction film references hidden throughout the funky decor. 

Best Views in Key West 

Just off Mile 0 Duval lies the world famous Mallory Square and its sensational southernmost sunsets. Feline ringmasters and acrobatic street performers gather alongside artists and food vendors for a high-energy evening of zaniness. Get there early to secure a spot close to the water’s edge. While you’re at it, seek your fortunes from local tarot card reader, Ronald Augustine. 

RELATED: A Cruiser’s Guide to Key West 

Angling for even more time on the water? See island life from a wetter perspective with a private, four-hour leisure or fishing adventure aboard a private charter. Discover the dolphins, sandbars, and glistening underwater scenery with your closest friends and family led by an experienced hand such as Zia Charter’s Captain Jeremy. 

Key West is All Culture 

Step back in time at the San Carlos Institute. This testament to Cuban-infused architecture is a cultural monument in the middle of Duval t. The institute formerly hosted Cuban philosopher José Martí’s rousing speeches, housed one of the country’s first bilingual and integrated schools, and celebrated annual festivities including….

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By Kevin Assam

Photo: Fritas Cuban Burger Cafe

Now in its 25th year, Porthole Cruise and Travel Magazine is published bi-monthly and available worldwide through digital subscription. It offers the latest news in cruise and travel, with in-depth features on voyages, new ships, the best destinations, readers' picks, onboard cuisine, entertainment, and more!