Taking a Big Bite Out of Little Havana with a Food and Walking Tour

Where we’re at: I’m recapping my summer of 2018, which included this trip to Florida in July. Want to explore Florida with me? Be sure to nab one of the last few spots to our Wander Women Key Largo: A Sustainability Dive + Yoga Retreat rescheduled for July 15-18, 2021.

Miami wouldn’t be Miami without its Cuban flavor. Which is why I couldn’t believe I’d waited until my third trip there to finally get my Latin-culture loving booty over to Little Havana! I’d read enough about the area to know that there weren’t really huge sights or attractions to tick off; visiting Little Havana is more about soaking up the atmosphere, learning about the history of Cuban Americans in Miami, and of course, enjoying one of their greatest gifts to the city — their food.

While I often love to just explore a new city of neighborhood on my own, I was really keen on getting the full vibrant Calle Ocho experience — I didn’t want to just wander aimlessly, take a few token photos, and randomly chose a Cuban sandwich to scarf down. I knew a tour by someone with a personal connection to the neighborhood was the way to go here.

So, after having a great experience with a food tour of South Beach on my very first trip to Miami years ago, I signed Ian and I up for a Little Havana Food and Walking Tour with the same company.

We made our way from South Beach to the Agustin Gainza Arts and Studio where our tour began and chatted with our incredibly friendly guide while mentally preparing our stomachs for an overload of Cuban delicacies like flan ice cream, chicken and picadillo-stuffed plantain cups, guava pastelito, cubano coffee, guarapo juice and more.

Like the gallery we were kicking off our tour in, all the restaurants we’d be visiting that day were family owned and operated, and eager to share Cuban culture with the curious.

We’d arrived hungry, and so were thrilled when our first stop was just steps away at the charming El Pub Restaurant. Here, we tucked into picadillo-stuffed empanadas, a strong start I wondered if we’d be able to beat. We also sampled Café Cubano here, from the onsite La Ventanita, translated to “the little window” in English, where countless Little Havana locals pop by and start their day with a shot-sized dose of the potent, espresso-like and super sweet fuel. While I love the idea of such a sweet and punch-packing little dose of energy, my lifelong aversion to coffee sadly didn’t end here.

While I can’t say I’m a huge fan of cigars either, I did enjoy our quick wander through the The Cuba Tabacco Cigar Co., if only to meet our gregarious host, the patriarch of the Bellos family. Involved in the Cuban cigar business for over a hundred years, they certainly know their stuff, and I loved watching the tobacco-stained fingers of the masters at work — until my allergies got the better of me and I had to step outside for some fresh air, anyway.

Next up? A major hit on my end — guayaba pastelitos, or guava pastries, from Yisell Bakery. While they weren’t something I’d have picked out for myself, I adored the smooth, flakey and flavorful dessert — discoveries like this are one of the reasons I love culinary tours that push me outside my comfort zone a bit.

Next up? The place in Little Havana I was most itching to visit — the iconic Ball and Chain. With a bandstand in the back shaped like a pineapple and the best mojitos in Miami served up in the bar up front, it’s like a dream come true for the modern millennial — though having first opened its doors in 1935, this bar and lounge holds decades and decades of history.

Between stops, our guide told us the stories not just of the food and drinks but of those doing the cooking and the pouring — the family recipes passed down for generations, the spiritual beliefs of those practicing Santeria, the political struggles of a fascinating nation three hundred and thirty miles away. While Little Havana is a very compact geographical area, the culture spills out into all of Miami, and you’ll feel like you’ve visited another country without ever whipping out your passport.

Our mojitos were followed by another quintessentially Cuban drink — guarapo fruit juice from Los Pinarenos Fruteria. Made of fresh mango, sugarcane juice, and whatever else was fresh, it was tropical bliss in a sip (though I’d love to see them ditch the unnecessary plastic straws). Our guide pointed out several exotic South Florida fruits we were likely to be unfamiliar with, and I went crazy with my camera and all the colors.

The tour was perfectly timed so that we were ready for our next big bite — authentic Cubanos at Old Havana Restaurant. Made with cuban bread, yellow mustard, roast pork, glazed ham, swiss cheese, and thinly sliced dill pickles, it’s not a sandwich I’d have ever ordered for myself. Still, I enjoyed my half-sample (Ian was more than happy to finish off the rest) and am grateful for the opportunity to have tried such a classic Cuban dish in such an authentic way.

Weaved throughout our food stops, we stopped at famed Calle Ocho landmarks like Domino Park and the Cuban Memorial Boulevard.

Domino Park is exactly what you’d guess; a park where locals — often retired older residents — spend their days playing dominos, as well as chess and checkers. Once upon a time, locals would crowd into the barren space with fold up chairs, plastic crates and homemade game pieces. In the 1980’s, the local government remodeled the park into the much loved community space it is today.

At the Cuban Memorial Boulevard, our guide touched briefly on the Bay of Pigs Invasion Memorial and the many political struggles commemorated by demonstrations in this very square.

Our final stop was, unsurprisingly, a sweet one –mantecado ice cream at Azucar, an ice cream shop that promised to combine abuelita’s secret recipes with fresh and local flavors and ingredients.

This tour is more than just the food — it’s traditional Cuban music wafting from a window, it’s overhearing more conversations in Spanish than English, it’s the genuine warm hugs and greetings you’ll see your guide getting from locals. We learned so much about the culture, visited in a respectful way, and supported small local businesses — exactly what we’d hoped for.

The Little Havana Food and Walking Tour departs daily at 11:30AM, 12:30PM, and 3:30PM, lasts 2.5 hours, meanders about half a mile, and costs $56USD. I’m a fairly picky eater (less so as the years tick on) and while I don’t love coffee and cuban wouldn’t be my go-to order, I tried everything on the tour and enjoyed all of it — minus the coffee, sorry brew fans! I also found it to be a very generous serving of food. As always, this tour operator does accommodate food restrictions with a heads up, however this tour in particular is not recommended for vegan or strictly gluten-free guests.

The same operator also does a shorter version of their Little Havana tour, a South Beach food tour, a Coconut Grove food tour, a Wynwood food tour, and a Design District food tour (the last of which is top of my list for my return).

Want to linger longer in Little Havana? Check the movies at the iconic Tower Theater, have a cocktail at Nancy’s Bar or a brew at Union Beer Store, see what shows are happening in the pineapple bandstand at Ball and Chain, stay and wander through galleries — perhaps even long enough to stick around for dinner, if your appetite allows.

Without a doubt, I’ll be back for all of the above. And perhaps next, a trip to the big Havana!

Are you a food tour fan? Have you been to Little Havana?

I took this tour as part of a photography assignment with Viator and was compensated for my time. I was not asked to write a review on my blog but had a great time and wanted to share it with you!