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.

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

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.

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 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 aoli.

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.”

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.)

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 serve 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.

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.

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.

Foods You May Try on a Key West Food Tour

One of the best things about taking a food tour in Key West is the opportunity to sample the island’s signature flavors. While each tour has its own unique lineup of restaurants and tastings, many feature local specialties that reflect the city’s rich Cuban and Caribbean influences.

Depending on the tour and the season, you may have the chance to enjoy favorites such as:

• Fresh Key West pink shrimp, known for their sweet, delicate flavor
• Conch fritters, a classic Florida Keys appetizer served with a dipping sauce
• Cuban sandwiches, layered with roast pork, ham, Swiss cheese, pickles, and mustard on pressed Cuban bread
• Fresh seafood like mahi-mahi, grouper, or snapper prepared with local flair
• Key lime pie, the island’s most famous dessert and a must-try while visiting
• Cuban coffee, a bold and sweet espresso that’s a staple of Key West’s café culture
• Island-inspired cocktails, which may include tropical flavors and locally crafted spirits for guests of legal drinking age

One of the things I enjoy most about food tours is that no two experiences are exactly alike. Seasonal ingredients, chef specialties, and restaurant partnerships can all influence what’s served, making each tour a unique culinary adventure.

What Should You Wear?

Key West is warm for much of the year, so comfort is key.

I recommend bringing:

• Comfortable walking shoes
• Lightweight clothing
• Sunglasses
• Sunscreen
• A hat
• Water bottle
• Small umbrella during summer showers

The route is mostly flat, but you’ll be outdoors for much of the tour.

Tips Before You Go

A few things can make your experience even better.

• Don’t eat a big meal beforehand.
• Arrive a few minutes early.
• Let the tour company know in advance about food allergies or dietary restrictions.
• Bring a camera—there are plenty of colorful photo opportunities along the route.
• Consider taking the tour early in your Key West vacation so you can revisit your favorite restaurants later.

That last point is something I always recommend after taking food tours.

Frequently Asked Questions

How long is the Southernmost Walking Food Tour?

Most guests should plan on spending approximately three hours enjoying the food, walking between stops, and learning about Key West’s history.

Is the tour family-friendly?

Yes, although families should consider whether younger children will enjoy several hours of walking and food tastings.

Can dietary restrictions be accommodated?

Many food tours can accommodate certain dietary needs with advance notice. Contact the tour operator before booking to discuss allergies or special diets.

Do I need to book in advance?

Yes. Popular tours often sell out, especially during peak travel seasons, so reserving your spot ahead of time is recommended.

Why Food Tours Make Great First-Day Activities

Whenever I visit a new city, I love scheduling a food tour early in the trip. Besides introducing me to local flavors, it’s one of the fastest ways to get my bearings and discover restaurants I’d probably overlook on my own.

Our guide pointed out local favorites, shared bits of Key West history, and offered recommendations we were able to use throughout the rest of our stay. By the end of the tour, we not only had full stomachs but also a much better feel for the island.

This section is unique to your experience and adds a personal touch that generic travel sites can’t replicate.

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

Final Call

The Southernmost Walking Food Tour combines local history with some of Key West’s best restaurants, giving you the chance to sample authentic island flavors while exploring neighborhoods you might otherwise miss. Rather than wandering Duval Street wondering where to eat, you’ll enjoy curated stops and hear the stories behind the food and the island’s unique culture.

After indulging in conch fritters, Cuban sandwiches, and tropical cocktails on the Southernmost Walking Food Tour, keep exploring Key West’s flavors and charm. Stay in style at Kimpton’s Winslow’s Bungalows, step back in time at the Ernest Hemingway House, or round out your itinerary with more Top Things To Do in Key West. Together, these stops create a full-on island experience worth savoring.

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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