The Southernmost Food Tour: Eating our way around Key West

One of my favourite ways to understand a destination is by simply eating the local cuisine. I mean who doesn’t enjoy taking a gastronomic tour where you get to walk, talk, eat and drink your way through an area’s best restaurants, bars and culinary institutions?

Key West Food Tours are one of the best-known food tour groups in the Florida Keys. They offer three main food and drink tours around Key West. But their Southernmost Food Tour is the best excursion you can do if you want to eat like a local and get a full understanding of the island’s food culture.

Within half an hour of arriving into Key West, we were at Siboney Restaurant where we were ready to meet our Key West food tour guide, Analise Smith.

Analise has Cuban heritage in her family so she was well qualified to educate us on the Cuban food scene in Key West.

The Southernmost Food Tour: Eating our way around Key West, Florida

Key lime pies

El Siboney, Key West

El Siboney is one of the most famous Cuban restaurants here and has become something of an institution since it opened in 1984. You’ll find El Siboney in the Old Town and it’s an unassuming red brick building, yet constantly draws in the crowds for its authentic Cuban cooking.

So, if you want to eat here, seriously consider booking ahead.

The Southernmost Food Tour lasts three hours, but there’s a lot of eating to do. So Analise doesn’t mess about.

While our food was being prepared, she gave us a crash-course in how to drink Cuban coffee and the various ways you can order it.

There’s the Cafecito or Café Cubano (served in a thimble-sized cup), a Café con leche (coffee with steamed milk), a Cortadito (served with a tiny splash of steamed milk) or the Bucci (a strong shot of espresso that’s served with cane sugar.)

If there’s more than one of you, you can go with the tradition of ordering a Colada which is essentially an extra-large cup of the sweet Bucci, which you then share between several people in the thimble-sized cups (see picture below.)

Another Cuban tradition is also to order the ridiculously more-ish pan Cubano (Cuban bread) and dunk it in your drink. Delish.

Colada of Cuban coffee

Cubans have a very sweet tooth, or as Analise says, they’re ‘sweet freaks’. So adding sugar to the coffee is a given. If they ask you whether you’d sugar, they’re actually asking if you’d like even more sugar than what they automatically put in.

So you could be bouncing off the walls after tasting this. You have been warned!

Colada of Cuban coffee

The food dish we try at El Siboney is the classic roast pork, or Cuban Puerco Asadoas it’s known. If you read my review of Versailles in Miami, you’ll know that BC tried a dish like this there. However, I have to say, this one was tastier. It was served with white rice, fried plantain and a squeeze of fresh lime, with a hot sauce on the side. Delicious.

It was time to move on.

Cuban Puerco asado

Badboy Burrito

Badboy Burrito, our next stop, is a hole-in-the-wall restaurant and bar. It’s here you’ll pick up what are arguably, the best tacos and ‘build-your-own’ burritos in Key West. The long queue says it all.

It’s a no-frills kind of place, so you pull up a chair outside, grab a chilled drink and prepare to get your hands messy. The Southernmost Food Tour highly recommended we tried the fish taco. And for good reason. They’re made using ‘tile fish’, which are one of the most sustainable fish you can eat in the Florida Keys.

Many people are still unaware of this more ‘environmentally friendly’ choice of fish. And while I’d say it’s not bursting with flavour, it was certainly livened up by the salsa verde, sour cream and cilantro. The executive chef at Badboy Burrito is very passionate about using the freshest ingredients. So much so, they don’t even have freezers. You can guarantee on ocean-to-plate quality and you can’t beat the name either.

Fish tacos

A bit of history and culture

In between all the eating, Key West Food Tours will make sure they fill you in on the many cultural and historical places of interest you pass on the way. On the Southernmost Food Tour, Analise regaled us with all sorts of tales about Key West’s cigar-making history, the ‘shotgun houses’ where factory workers lived, as well as the stories behind the many quirky shops and houses you’ll find on the island, such as the Tomasita Seafood shop.

Tomasita Seafood, Key West

Thanks to its proximity to the Caribbean, Key West was a huge player in rum importation, even during America’s prohibition era.

And after all our walking, Analise decided it was time for a tipple – which takes us on to one of the island’s most famous speakeasies, The Rum Bar.

The Rum Bar, Key West

The Rum Bar

I’m a huge fan of rum, so it was a little disappointing that I was unable to make the most of this bit, being six months pregnant! But whether you’re drinking alcohol or not, The Rum Bar is an interesting place to visit. You’re bound to meet a quirky character or two.

You’ll find The Rum Bar on Key West’s famous Duval Street and it was originally owned by a man called Raul Vaquez, who was a cigar selector at the island’s famed Gato cigar factory.

They stock an impressive 250+ types of rum, which you can of course sample straight, or in one of their many classic cocktails.

Apparently Vaquez’s true passion was working as a ‘rum runner’ between Key West and the Caribbean. The industry became so in-demand, they established a ‘rum row’ – a three-mile route between Key West and Bermuda where ‘rum runners’ travelled back and forth.

So it only seemed right that on the Southernmost Food Tour, the group tried the synonymous Rum Runner cocktail – a mix of white and dark rum, banana, blackberry, grenadine, OJ, pineapple and sours. Meanwhile, Analise kindly ordered me a Rum Runner sans alcohol.

Man with long beard and dog

Livened up and ready to go, our next stop on the Key West Food Tour was the Bahama Village, one of my favourite areas of Key West and where the majority of Key West’s Caribbean community settled.

Analise filled us in on the history of the colourful clapboard houses and stopped by key points of interest such as the much-loved Rick Worth mural….

Rick Worth Mural, Key West

…and the family home of legendary trumpeter Theodore “Fats” Navarro.

Home of Theodore “Fats” Navarro

But our next stop on the Southernmost Food Tour was another Key West institution, Blue Heaven.

Blue Heaven

If you’re ever in Key West, this is probably the restaurant I’d recommend as a great all-rounder. Positioned within a leafy garden, complete with roaming roosters and a rooster cemetery (they love their roosters here), an outdoor bar and quirky knick-knacks, it’s packed with that Bohemian charm you’ll find in many parts of Key West…

Blue Heaven, Key West

…and they serve a Key Lime Pie that’s to die for.

As you’ll learn on this gastronomic journey, Key Lime Pie is a classic Key West dessert and there are all sorts of variations in how it’s served.

Here at Blue Heaven, we tried it in miniature form, comprising of a delicious biscuit base and a tangy lime filling topped with a pillow-soft meringue.

Key Lime Pies

They were so tooth-achingly sweet, these cute little miniatures were more than enough. If you’re keen to try the many variations of this local treat, head to the many Key Lime Pie shops and factories in the Old Town and sample them all!

We headed back to Blue Heaven for a great brunch a couple of days later and I’d highly recommend a visit.

Lamp at Blue Heaven, Key West


Mangoes is more of a mainstream bar and restaurant you’ll find on Duval Street. But its indoor-outdoor feel and smart cocktail bar vibe definitely make it worth visiting. As we discovered on the food tour, it’s also a great place to sample another culinary staple, conch. 

Mangoes, Key West

Conch is the sea snail you’ll find in abundance in Key West. It’s also what many people still nickname themselves here after the tongue-in-cheek movement in 1982 which saw Key Westers form a micronation dubbed the ‘Conch Republic’.

These squidgy molluscs are commonly used to make ceviche and chowder but you’ll also find them shallow-fried, or deep fried to make fritters. At Mangoes, they were served as fritters with a delicious aioli made using the local Key Lime.

They’re perfect as a tasty snack and taste even better when enjoyed in the sun, with a refreshing beer.

Side note: Part food baby, part real baby growing in my tummy here..

The Travel Journo, Lucy McGuire

Conch fritters

Key West Distilling

Our final stop on the Southernmost Food Tour was Key West Distilling, a small distillery on Southard Street that produces craft spirits, rums, vodkas, gin and whiskey.

Again, I had to smell rather than taste, but Analise provided an interesting introduction into their unique distilling processes, the ways they produce the oak flavours and the various ingredients and spices that are used here.

If you’re brave enough, you’ll try the overproof rum which has a mighty 76.5% alcohol content. Or maybe you’ll sample the horseradish vodka?

Bottles of Key West rum

Barrels in Key West Distlling

Key West Distilling

Either way, it was a great end to a fantastic excursion with Key West Food Tours.

I’m so glad we did the Southernmost Food Tour as soon as we arrived into Key West. It offered a great introduction to the island, it taught us a lot about the Florida Keys culture and we left with a long list of recommendations on places to eat and drink, which is never a bad thing.

The Southernmost Food Tasting & Cultural Walking Tour costs from $75 for adults and $49 for children aged 12 and under. You can find out more about Key West Food Tours on Facebook, instagram, twitter and via their website.

Find out more about the Florida Keys and Key West via the Florida Keys and Key West Tourist Board.

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My ticket for the Southernmost Food Tour was organised by the Florida Keys Tourist Board
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