Taste the flavors of Key West on a sweet and savory food tour

El Siboney restaurant, known for Cuban roast pork, is a stop on the Southernmost Food Tasting and Cultural Walking Tour in Key West, Florida. 
Courtesy of Newman PR

Credit: Handout

Credit: Handout

El Siboney restaurant, known for Cuban roast pork, is a stop on the Southernmost Food Tasting and Cultural Walking Tour in Key West, Florida. Courtesy of Newman PR

While nibbling a flaky chicken empanada in a poolside cabana at the Havana Cabana hotel in Key West, Florida, it dawned on me that my familiarity with Caribbean flavors does not extend to Cuba. Courtesy of the hotel’s food truck, Floridita, I had been dining regularly on Cubano sandwiches, filled with roast pork, ham and Swiss cheese, and ropa vieja, a shredded beef dish traditionally served over rice but stuffed in a roll here. I savored these meaty treats but wondered why Cuban fare wasn’t as seafood-centric as other corners of the Caribbean. And where was the spice?

The conundrum inspired me to tuck deeper into this distinctive cuisine, so I joined the Southernmost Food Tasting & Cultural Walking Tour, a flavorful, three-hour journey by foot through Key West that highlights the island’s Cuban and Caribbean influences.

A Havana Cabana guest enjoys a meal from the hotel's Floridita food truck. 
Courtesy of Havana Cabana.

Credit: Handout

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Credit: Handout

El Siboney restaurant, the first stop, is a Key West landmark cherished by locals of Cuban descent, like Analise Smith, the tour company owner and guide.

Who knew so much history could be on a plate of puerco asado, or shredded roast pork?

Smith explained that Cubans' love of pork can be traced back to the 15th century when Spanish colonizers introduced pigs and cattle to a people that had subsisted mostly on seafood. They’ve been eating high on the hog ever since, serving it at almost every holiday and special occasion.

El Siboney serves succulent roast pork so tender you could eat it with a spoon. It’s piled high with onions and topped with a lime wedge that’s meant to be squeezed over the fragrant meat. A mound of white rice, a sweet plantain and a bowl of black beans round out this “tasting” that is more of a full-blown meal.

The meat gets its tangy zip from a mojo sauce marinade made from sour orange, garlic and Cuban oregano. It’s flavorful, but not spicy.

“There’s a common misconception that ‘Hispanic’ foods are spicy, primarily coming from people who are familiar with Mexican cuisine, which uses hot peppers,” said Smith. “Cuban cuisine has spice, but there’s no heat. You’ll never see Cubans putting hot sauce on their food.”

Even humble black beans and white rice, an everyday staple, reflects Cuba’s multi-cultural heritage. It’s called Moros y Cristianos, Moors and Christians, a reference to Medieval Spain when North African Muslims and European Christians battled for control of the Iberian Peninsula. It’s likely the Moors introduced the dish to Spain, and the Spanish brought it to Cuba.

The Southernmost Tasting and Cultural Walking Tour in Key West, Florida, introduces visitors to the island's Cuban and Caribbean flavors. 
Courtesy of Newman PR

Credit: Handout

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Credit: Handout

Enslaved Africans who labored on Cuban sugar cane plantations ushered in their own culinary traditions, such as mixing white rice with a variety of vegetables and sauces.

When we had our fill, we hit the sunny streets for a little sightseeing, sidestepping the lethargic feral cats that rule the island. Smith pointed out the Key West Lighthouse and the long-shuttered Gato cigar factory that produced cigars made with robust Cuban tobacco.

Raul Vasquez, a prominent Key West citizen, was a cigar selector there, but he had a far more interesting side gig as a Prohibition-era rum runner.

He once owned what is now the Speakeasy Inn, home to the iconic Rum Bar. As we sipped rum punch on the breezy front porch of the historic property, we heard about how his frequent trips across the Straits of Florida kept his not-so-secret Florence Club in the back of the inn stocked with fine Cuban rum.

Prohibition ended long ago, but the U.S. enforces import restrictions on Cuba, so commercial importation and distribution is still illegal. At the Rum Bar, drinkers make do with a selection of 350 rums from around the world and an impressive list of rum cocktails that includes the house specialty, the Painkiller, a riff on the Piña Colada. Blend Pusser’s rum with coconut cream, orange juice and pineapple juice, sprinkle with a dusting of fresh nutmeg, and you’ve got a panacea for whatever ails you.

Conch fritters from Mangoes restaurant are served on the Southernmost Food Tasting & Cultural Walking Tour. 
Courtesy of NewmanPR.

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Credit: Handout

Rounding up a herd of content rum-imbibers proved to be a bit of challenge, but Smith eventually persuaded us that a world of gastronomic delights awaited, if we would only pry ourselves out of those comfy chairs.

We were well rewarded for our efforts at Mangoes, a Duval Street restaurant known for Caribbean classics such as fish tacos and deep-fried conch fritters served with a dollop of key lime caper aioli. These are the Caribbean seafood dishes I know and love, and I could have wolfed down every last one of those delectable fritters.

Duval Street has its share of fine restaurants and other attractions, but this tour goes beyond the touristy hotspots and onto charming side streets.

Bahama Village, a 16-block Old Town neighborhood founded by 19th-century Bahamian immigrants, features rows of pastel cottages with tropical flowers tumbling over fences with quirky cut-outs. The neighborhood teems with restaurants and bars with a cool calypso vibe.

“A lot of people think of Key West as just a big party town, and they stay on Duval Street,” said Smith. “But this a culture-filled town with a rich history that has been passed down through generations of families, so I’m proud to share a different side of the island.”

Dessert is served at Moondog Café & Bakery, an eatery with eye-catching murals reflecting Key West life. Key lime pie is an American creation without Cuban or Caribbean roots, but who cares? You can’t have a Key West food tour without a slice.

One bite delivers a trifecta of contrasting textures and flavors — a delicate graham cracker crust, a tart-sweet filling made with condensed milk and a puffy cloud of meringue on top. There’s a longstanding meringue versus whipped cream debate among “conchs,” as Key West residents are called, but since practically every restaurant in the city serves some version of this Southern specialty, finding your topping of choice is easy as pie.

I return to the hotel not only sated by delicious Cuban and Caribbean fare, but full of knowledge about the cultures that brought those flavors to Key West. But now I’m curious about the origins of Key lime pie. I guess that’s a food tour for another day.


Key West, Florida, is 820 miles south of Atlanta. Non-stop flights from Atlanta are available on Delta Air Lines.


Southernmost Food Tasting & Cultural Walking Tour. $75. 305-570-2010, www.keywestfoodtours.com. Tour begins at El Siboney.


Floridita. Poolside food truck at Havana Cabana hotel that serves authentic Cuban food. Entrees $12-$17. 3420 N. Roosevelt Blvd., Key West, Florida. 305-294-5541, www.havanacabanakeywesthotel.com

El Siboney. Authentic Cuban food. Entrees $12-$22. 900 Catherine St., Key West, Florida. 305-296-4184, www.elsiboneyrestaurant.com

The Rum Bar. Speakeasy Inn, 1117 Duval St., Key West, Florida. 305-296-2680, www.speakeasyinn.com

Mangoes. Caribbean-inspired fare. Entrees $22-$36. 700 Duval St., Key West, Florida. 305-294-8002, www.mangoeskeywest.com

Moondog Café & Bakery. Serves breakfast, lunch and dinner. Entrees $18.50-$32. 823 Whitehead St., Key West, Florida. 305-741-7699, www.moondogcafe.com


Havana Cabana. Waterfront Cuban-themed hotel. $159 and up. 3420 N. Roosevelt Blvd., Key West, Florida. 305-294-5541, www.havanacabanakeywesthotel.com

Barbary Beach House Key West. A Caribbean-style, all-suite hotel on Smathers Beach. $254 and up. 2001 S. Roosevelt Blvd., Key West, Florida. 305-292-9800, www.barbarybeachhousekeywest.com