Key West Southernmost Walking Food Tour

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To truly get a taste of Key West, book a food tour where every bite is a journey through the city’s culinary history. The Southernmost Food Tasting and Cultural Walking Tour takes you on a delightful adventure, introducing you to iconic dishes, hidden gems, and the fascinating stories that make Key West’s food scene so unique. Don’t miss the chance to savor the flavors and uncover the delicious secrets of this tropical paradise!

Collage of food pictures taken in Key West, Florida.

When we travel, we love to book a food tour for the first day or two of our time at our destination. It’s one of the best ways to discover some cool restaurants that fly under the radar as well as learn about the history of the city. The Southernmost Food Tasting and Cultural Walking Tour in Key West, Florida is no exception. It ranks among the best food tours that we have taken.

We searched for Key West food tours and came across the Southernmost Food Tour. It is a 3-hour guided tour that takes place in Old Town Key West highlighting local cuisine and the history of Key West. Limited to a cozy group size of just 12, it ensures an intimate and personalized exploration of the city’s culinary delights.

1. El Siboney Restaurant

Our meeting point and first stop were at El Siboney at 900 Catherine Street where we enjoyed authentic Cuban cuisine. We were served mojo pork with pickled onions, sweet plantains, rice and beans, and Cuban bread. Mojo pork is made with a sour orange and herb marinade. The pork is marinated overnight and then slow-roasted until tender. The pickled onions we were served had a Cuban twist – they were pickled in lime juice. We learned that Cubans use the whole pig, which meant that the Cuban bread we had was made with pork lard.

A plate with pulled pork, rice, beans, and Cuban bread.

Something else that we learned during our meal is that the name of the restaurant, El Siboney, refers to the native people of Cuba (the Siboney tribe). Speaking of Cuba, before the Spaniards arrived in the 15th century, the diet of the natives consisted of seafood, tropical fruits, and yucca. Chicken, beef, and pork did not make their way to Cuba until the Spaniards arrived in the 15th century.

We wrapped up our time and headed to our next destination, Speakeasy Rum Bar. On the way, some of the shotgun houses were pointed out and we were told how Eduardo Hidalgo Gato, a cigar-maker, built 40 homes, including the shotgun houses, in Key West for housing for his employees. The area became known as Gatoville.

2. Speakeasy Rum Bar

Man standing behind a bar.

We arrived at Speakeasy Rum Bar at 1117 Duval Street and sampled the rum runner. (Rum runners are made with rum, banana liqueur, and grenadine.)

Prohibition, the time when it was illegal to make or sell alcohol (1920 – 1933), gave birth to speakeasies, places where it was illegally sold.

The Speakeasy Rum Bar was originally owned by Raul Vasquez, who worked for Mr. Gato, the aforementioned cigar maker.  Once a 2 bedroom home, it was converted into a 7 room brothel in the 1920s. The second-floor balcony is lined with balustrades (railings) shaped like bottles and hearts, subtle shapes that were a nod to what took place at the building.

Jeff and Lynda at a bar.

One of the interesting facts is that the inn/rum bar is one of three homes that has a basement in Key West. This may not sound interesting, but when you take into account that the island has a high water table and is close to the ocean, it’s practically impossible to have a basement there.

When we finished enjoying our drink, we walked nearly ½ a mile to our next destination. On the way, we walked past the Key West lighthouse and stopped in Bahama Village. We learned a little bit about the history of an old wooden church that has been converted into a home. Today, that building is protected by the historical society.

3. Mangoes

Our third stop was at Mangoes at 700 Duval Street where we would sample one of Key West’s signature dishes – conch fritters. Similar to calamari, conch meat is chewy.

Mangoes Island Cuisine restaurant in Key West.

Mangoes fritters are made like a hushpuppy, but instead of cornmeal they are made with flour and they have bell peppers and carrots, and are served with key lime aioli.

While there, we also sampled their conch chowder which is a Manhattan-style chowder, meaning that it is a red chowder and it has onions carrots, celery, and potatoes.

Things that we learned at this stop are that it is illegal to harvest conch in Florida. Due to overfishing in the 1970s, Florida banned it. Don’t pick up a conch shell if you find one in the water. It’s perfectly okay to buy one at a store.
Also be sure to pronounce it “konk“, not “kaunch” – unless you want to get looked at funny.

4. Kaya Island Eats

Just a short walk away was our fourth stop – Kaya Island Eats at 628 Duval Street, a cool restaurant that serves “island fusion cuisine.”

Kaya Restaurant in Key West.

We were served Floribbean aka Reggae fish – Jamaican jerk mahi over coconut saffron rice with jerk sauce, goat cheese, and mango salsa. (It was my favorite dish that we tried on the tour.)

A plate of Raggae Fish with rice, pineapple, and cilantro.

We also sampled Juju’s Maui Mai Tai, their signature cocktail made with silver rum, real passion fruit, almond syrup, and pink lemonade.

We learned about the owner’s background, which, if my memory serves me correctly, was that came from Hawaii. That would explain why the signature dish is Ahi Poke nachos. (They also serve Hawaiian pork sliders and a “Polynesian Party” that features grilled shrimp with pineapple and a toasted coconut Thai chili dressing.)

Botanical Gardens

Our next stop was a diversion at The Gardens Hotel. We are not going to show you pictures of the hotel, but rather the attached botanical gardens which are a hidden gem and free to visit.

In 1930, Peggy Mills had a vision of turning the property of the Gardens Hotel Key West into a botanical garden open to the public free of charge. She went so far as to buy one-quarter of a city block and demolish the existing buildings to create her garden.

Peggy collected plants from all over the world and she became known as “The Lady of the Orchids.” She also bought old bricks from Cuba, Honduras, and England. From Cuba, she acquired four earthenware jars called tinajones that weighed one ton each. It was a feat transporting them and today they are the only tinajones in the United States.

5. Cuban Coffee Queen

Our final stop was at the Cuban Coffee Queen at 5 Key Lime Square, renowned for its – wait for it – Cuban coffee. Here we would sample two items that Southern Living deemed one must order on the island.

Woman holding a frozen chocolate dipped Key Lime pie slice.

Cuban coffee, also known as “Café Cubano,” is a type of strong and sweet coffee that originated in Cuba. It is made using finely ground espresso coffee beans and is brewed using an espresso machine or a stovetop espresso maker called a “moka pot.” The coffee is typically served in small cups called “tacitas” and is often sweetened with demerara sugar, creating a distinctively rich and sweet flavor.

We had a small sample of the coffee and then got to enjoy the fruits of a difficult decision we had to make earlier in the day: did we want a slice of traditional key lime pie or key lime pie on a stick?

I chose the chocolate-dipped frozen pie while Jeff picked the traditional. I think we were both happy with our choices.

Woman holding a frozen chocolate dipped Key Lime pie slice that had a bite taken out of it.

Five Reasons To Book a Food Tour

  1. Diverse Culinary Delights: Key West boasts a melting pot of flavors influenced by Caribbean, Cuban, and Southern cuisines. A food tour lets you taste a variety of mouthwatering dishes, from fresh seafood to authentic Cuban sandwiches.
  2. Local Insights: Food tours are guided by knowledgeable locals who share fascinating stories about the city’s history, culture, and culinary traditions, offering a deeper understanding of Key West’s unique identity.
  3. Hidden Gems: Discover hidden culinary gems and off-the-beaten-path eateries that you might miss without insider knowledge. These spots often serve up some of the most authentic and delicious dishes in town.
  4. Fun and Interactive Experience: Food tours are engaging and interactive, creating a dynamic environment for meeting fellow food enthusiasts, trying new dishes, and enjoying a social adventure through the city.
  5. Time-Efficient Exploration: In just a few hours, a food tour allows you to explore various dining hotspots, giving you a taste of Key West’s culinary scene without spending days hopping between restaurants.

Your tour guide and experience will most likely be different than ours, but you are still bound to have a great time.

Interested in going? You can learn more about the tour by clicking on the (paid) link below.


Have you taken the Southernmost Food Tasting and Cultural Walking Tour in Key West? What did you think? Have you been on other food tours? We would love to read about your experience(s) in the comments below.

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5 Comments

  1. really wish the tour would have ended up where we started, our guide just dumped us to find our way back.
    the food was good, but being unfamiliar with Key West, made the experience undesirable.

  2. (1) I didn’t see the link for the Key West food tour (2) what plane to you fly? I made my first trip to Key West in a Cessna 172.

    1. 1) The link is by a small picture and says “Book Now.”
      2) We flew on a Delta jet. I think I would have been scared on a Cessna 172. You’re a brave soul.

  3. Nice start at ElSiboney but you should have gone south east to Louie’s …. 5 Brothers (Pepe) Grocery store at Grinnell and Southard has better coffee and great sandwiches at less price than Cuban Coffee Queen (Id like to be the PR firm for Cuban Coffee Queen). The deli across from Green Parrot Whitehead St is worh a mention as well….
    I guessyouncan figure out that I like the locals places better than the tourist places….

    1. I thought it was a nice food tour. Two places that were not on the tour that we enjoyed were Pepe’s and Harpoon Harry’s for breakfast.

      We appreciate your comment and insight.

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