12 Cuban Sandwiches Across Florida Worth Trying

Florida’s love affair with the Cuban sandwich runs deep, from Miami to Tampa and beyond. This iconic sandwich, with its perfect blend of roasted pork, ham, Swiss cheese, pickles, and mustard pressed between crispy Cuban bread, has countless variations across the Sunshine State.

I’ve traveled the state to find the most mouthwatering Cuban sandwiches that showcase Florida’s diverse culinary heritage.

1. Versailles Restaurant’s Classic Cuban

Nothing beats the iconic status of this Little Havana landmark. Since 1971, locals and tourists alike have flocked to this Miami institution for their perfectly pressed sandwiches.

The bread achieves that ideal balance – crispy exterior with a soft inside. Their roasted mojo pork practically melts in your mouth, complemented by the tang of yellow mustard and pickles.

For the authentic experience, enjoy it with a colada (Cuban coffee) at their walk-up window like a true Miamian.

2. Columbia Restaurant’s Historic Tampa Cuban

Founded in 1905, Columbia Restaurant claims to serve Tampa’s original Cuban sandwich, complete with their controversial addition – Genoa salami. The Italian influence comes from Ybor City’s immigrant history, creating a uniquely Tampa twist.

Each sandwich gets pressed on a hot plancha until golden brown. I love how the Swiss cheese melts perfectly into the layers of meat while the bread develops that signature crackly crust.

Pair it with their renowned Spanish bean soup for a meal that spans generations of Florida history.

3. La Segunda Bakery’s Authentic Cuban

The secret weapon at this Tampa institution is their handmade Cuban bread, baked fresh daily since 1915. Each loaf comes with the signature palmetto leaf strip on top – a tradition that creates the perfect split down the middle.

When I bite into their Cuban, the freshness of that bread makes all the difference. The ham is carved in-house, and they don’t skimp on the roast pork.

What makes this place special is watching the multi-generational bakers work their magic before your sandwich even begins its journey.

4. Enriqueta’s Sandwich Shop’s No-Frills Masterpiece

Hidden in Miami’s Wynwood neighborhood, this unassuming counter-service spot serves what many locals consider the city’s best Cuban sandwich. There’s nothing fancy about Enriqueta’s – just consistently excellent execution.

Their sandwich comes stuffed with generous portions of slow-roasted pork that’s marinated in a family-secret mojo. The bread gets a liberal coating of butter before hitting the press, creating an irresistible golden crust.

Ask for a side of their homemade hot sauce for an extra kick that cuts through the richness perfectly.

5. Sarussi Cafe’s Massive Original

Size matters at this Miami institution, where their signature sandwich stretches a whopping 16 inches long! The Sarussi Original isn’t your traditional Cuban, but rather a delicious variation featuring smoked ham, roast pork, pickles, and melted mozzarella.

What makes it unique is their secret “Sarussi sauce” – a tangy, slightly spicy spread that elevates every bite. The bread gets hollowed out slightly before filling, creating the perfect meat-to-bread ratio.

Come hungry or plan to share – this monster sandwich could easily feed two people!

6. El Cochinito’s Award-Winning Cuban

When a sandwich wins the “World’s Best Cuban Sandwich” competition, it deserves your attention. This Little Havana gem earned that title with their perfectly balanced creation featuring 24-hour marinated pork leg.

Family recipes passed down from Cuba give their sandwich authentic flavor. The bread develops an audibly crunchy exterior while maintaining a soft interior – exactly what you want in a proper Cuban.

Pro tip: Their house-made chipotle mayo makes an excellent dipping sauce if you’re feeling adventurous with your traditional Cuban.

7. The Cuban Sandwich Shop’s Old Florida Treasure

Tucked away in St. Petersburg, this family-owned spot has been serving the same recipe since 1975. Walking in feels like stepping back in time – complete with vintage decor and friendly staff who know many customers by name.

Their Cuban comes wrapped in paper, allowing the sandwich to steam slightly before you unwrap your treasure. The bread has that perfect crackle while the interior remains moist with butter and pork juices.

Don’t miss their homemade flan for dessert – the perfect sweet ending to a savory classic.

8. Luis Galindo’s Latin American Cafe’s Media Noche

For a delicious twist on the classic Cuban, try the Media Noche (midnight sandwich) at this Miami favorite. Instead of Cuban bread, it’s served on a sweet egg bread similar to challah, creating a wonderful sweet-savory contrast.

The filling remains traditional – layers of roast pork, ham, Swiss cheese, pickles and mustard. However, the softer, sweeter bread transforms the experience entirely.

According to local lore, this variation got its name because the sweeter bread was gentler on late-night revelers’ mouths after hours of drinking and dancing!

9. Mary’s Cafe’s Seafood-Inspired Cuban Mixto

Located in Key West, Mary’s puts an island spin on the Cuban with their famous Mixto sandwich. Alongside traditional ingredients, they add a layer of local shrimp salad – a nod to the Keys’ seafood heritage.

The contrast between warm pressed sandwich and cool shrimp salad creates a temperature and texture playground in your mouth. Their bread gets a brush of garlic butter before pressing, adding another dimension of flavor.

Enjoy it on their outdoor patio with a cold beer while watching boats pass by for the full Keys experience.

10. Sloppy Joe’s Bar Havana-Style Cuban

Hemingway’s favorite Key West watering hole serves a Cuban with history. Their version pays homage to the original Sloppy Joe’s in Havana (where the famous sandwich originated) rather than the Tampa or Miami styles.

The difference is in the preparation – they use less mustard, more butter, and press the sandwich just enough to warm it through without creating the characteristic flatness. The result is slightly thicker with a softer texture.

Enjoy yours with their signature rum cocktail while live music plays in the background for a true Keys experience.

11. Sergio’s Restaurant’s Elena Ruz Sweet Variation

For something completely different, try the Elena Ruz at this Miami Cuban institution. Named after a 1930s Havana socialite who requested this special combination, it features turkey, cream cheese and strawberry preserves on sweet Cuban bread.

While purists might argue it’s not a true Cuban sandwich, its Cuban origins and popularity in Florida earn it a spot on this list. The sweet-savory balance creates an unexpected delight.

I recommend trying it for breakfast alongside a café con leche – the combination will change how you think about Cuban sandwich possibilities!

12. Brocato’s Sandwich Shop’s Devil Crab Cuban

This Tampa institution combines two local favorites – the Cuban sandwich and devil crab croquettes. Their “Devil Crab Cuban” places a spicy crab croquette directly inside the traditional sandwich before pressing.

The contrast between the crispy bread, melty cheese, savory meats, and the spicy seafood croquette creates an explosion of textures and flavors. It’s definitely not traditional, but it’s become a Tampa cult favorite.

Be prepared for a wait at lunch – locals line up daily for this unique creation that perfectly represents Tampa’s Cuban-Spanish-Italian heritage.