Tasty Travels Key West: Cuban Sandwich

Taste the Place — where culture, history, and flavor get pressed together

There are meals you eat…and then there are meals that tell a story.

The Cuban sandwich is one of those rare creations where every bite carries history—migration, hard work, and cultural fusion—pressed into something simple, portable, and unforgettable.

Where It All Began

While many assume the Cuban sandwich came straight from Cuba, its true roots live right here in Florida—shaped by Cuban immigrants who brought their traditions north.

In Key West, one of the earliest Cuban immigrant hubs in the U.S., the sandwich took form as a working-class staple:

• Built for cigar factory workers - a working man’s lunch
  
  
• Easy to carry, filling, and affordable
  
  
• Made with ingredients that reflected both Cuban heritage and local availability

This version is often considered the purest expression of the Cuban:

• Mojo-marinated roast pork
  
  
• Ham
  
  
• Swiss cheese
  
  
• Pickles
  
  
• Yellow Mustard
  
  
• Pressed on authentic Cuban bread
  

That’s it.

No extras. No overthinking.

Just balance.

(Side note: in Tampa, you’ll often find salami added—thanks to the Italian influence. In Key West and Miami, that’s considered sacrilegious. Both will tell you they’re right.)

The Bread That Makes It

The magic starts with Cuban bread—light, airy, with a crisp crust that shatters just enough when pressed.

It’s what separates a good Cuban from a real Cuban.

When pressed, the outside turns golden and crisp while the inside melts into a perfect blend of savory, tangy, and rich.

Without the bread, it’s not the same story.

A Taste of Key West Culture

Key West isn’t just a backdrop—it’s part of the recipe.

This is a place where:

• Cuban and American cultures have blended for generations
  
• Food reflects movement, resilience, and simplicity
  
• The flavors feel honest and unpretentious, just like the island itself

It’s the kind of meal you grab after a long walk down Duval Street, or before heading out on the water—nothing fancy, just exactly what it should be.

A Sandwich That Tells a Story

What makes this sandwich special isn’t just the flavor—it’s what it represents.

Migration.

Work.

Community.

Adaptation.

It’s the story of people bringing pieces of home with them and building something new in a different place—something that still holds onto where they came from.

You taste that in every bite.

Our Experience

We didn’t just make this—we live it.

Spending time in Florida, you start to realize quickly that this isn’t just “another sandwich on a menu.” It shows up everywhere, but the best ones always feel like they come from somewhere deeper.

There’s a rhythm to it:

The press.

The crackle of the bread.

The smell of the pork and mustard hitting the heat.

It’s simple. But it’s not basic.

📍 Where to Get the Best Cuban Sandwich in Key West

If you want the real experience, these spots deliver:

🥪 Sandy’s Cafe

A local favorite known for doing it the right way—simple, fast, and consistently excellent. This is the kind of place where locals grab lunch without thinking twice. Yes, it is next door to a laundromat on White Street-don’t let that fool you-this is a must stop! 

🥪 El Siboney Restaurant

More of a sit-down experience, but deeply authentic Cuban cooking. Their Cubano reflects the broader menu—rooted in tradition and flavor. True Cuban and a staple stop for you to get other items including traditional Ropa Vieja!

🥪 5 Brothers Grocery & Sandwich Shop

Part convenience store, part sandwich institution. Known for generous portions and a loyal following. A great spot on Southard-grab a cafe con leche for a fix in the am on your way to the boat and for other pickups including cold drinks.

Field Notes: Pressed Between Past & Present

There’s something fitting about the Cuban sandwich being pressed.

Because that’s exactly what it is—

cultures pressed together… histories layered… traditions carried forward.

And in Key West, maybe more than anywhere else,

you can still taste that origin in its purest form.

Tasty Travels — Taste the Place

That’s what this series is about.

Not just making something.

But understanding where it comes from.

Because when you do that—you’re not just cooking.

You’re bringing a place back to life.

This is the classic Key West-style Cuban—the pure version. No extras, no shortcuts. Just the right ingredients, layered and pressed into something unforgettable.

Ingredients (Serves 2)

🥖 The Build

• 1 loaf Cuban bread (or substitute: soft French or Italian bread-but there is a real difference in getting your hands on authentic Cuban bread)
• 8 oz mojo-marinated roast pork *future Tasty Travel*  (see below or use slow braised Pork Shoulder made at home or picked up at your local hot food deli or store)
• 4 oz sliced ham (sweet or smoked)
• 4 slices Swiss cheese
• Dill pickle slices (lengthwise)
• Yellow mustard
• Butter (for pressing)

Mojo Roast Pork (The Heart of the Sandwich)

Ingredients:

• 1–1.5 lbs pork shoulder
• 4 cloves garlic (minced)
• ½ cup orange juice
• ¼ cup lime juice
• 2 tbsp olive oil
• 1 tsp oregano
• 1 tsp cumin
• Salt & pepper

Instructions:

1. Mix all marinade ingredients together.
2. Coat pork thoroughly and marinate overnight (minimum 4–6 hours).
3. Roast at 325°F for 2–3 hours until tender and shreddable or internal temperature is at least 190 degrees F.
4. Slice or pull into sandwich-ready portions.

👉 Pro tip: Slightly crisp the pork in a pan before assembling for added texture.

🔥 Assembly & Press

1. Slice the bread lengthwise (keep it hinged if possible).
2. Spread yellow mustard on both sides.
3. Layer in order:

• Roast pork
• Ham
• Swiss cheese
• Pickles

    4. Close the sandwich and lightly butter the outside of the bread.
    5. Place in a sandwich press (or skillet with weight on top).

• Press until:
• Bread is golden and crispy
• Cheese is fully melted
   (about 3–5 minutes per side if using a pan)

Tasty Travels Note

This isn’t a sandwich that tries to impress—it just does.

The balance is everything:

• Citrus + garlic pork
• Salty ham
• Creamy Swiss
• Sharp pickles
• Crunchy pressed bread

And when done right, it tastes like Key West itself—layered, lively, and rooted in tradition.

Be sure to watch our how-to video on Instagram. Like and follow for more! 

Featured in the video, check out our Key West Travel Poster Merch.