Who Makes the Best Cuban Sandwich in Key West

A Foodie’s Guide to Finding the Best Cuban Sandwich in Key West  

Ever had a meal so good you thought, Hey, I could live off this forever? That’s how I feel about Cuban sandwiches here in the island paradise of Key West—a glorious spot where delicious Cuban flavors meet the laid-back vibe of southern Florida.  

Packed with roast pork, ham, Swiss cheese, pickles, and mustard, and pressed between the iconic Cuban bread, a Cuban sandwich is more than just food—it’s a slice of history (and trust me, it’s far better than any “cheese sandwich” you’ve grabbed in a hurry). And while Ybor City may claim to have created the original Cuban sandwich, Key West has put its own spin on this classic, proudly offering some of the tastiest versions you’ll find anywhere.  

Whether you’re a first-time visitor, a hardcore foodie, or just hungry after a day at Mallory Square, I’ve rounded up the best places to get this mouthwatering marvel. Bonus points? Many come with authentic Cuban coffee or some killer twists. 

What Makes a Cuban Sandwich Truly Cuban?  

Before we get into who makes the best Cuban sandwich, here’s a quick crash course for the uninitiated.  

A traditional Cuban sandwich (or “Cubano”) includes Cuban bread—a soft, handmade loaf brushed with lard for its chewy texture—stacked with slow-roasted pork, ham, Swiss cheese, pickles, and yellow mustard. No lettuce, no tomatoes, and absolutely no mayo on this classic unless it’s a local variation. The whole thing is pressed to perfection until the bread is crispy and the cheese is irresistibly melty.  

But in Key West, there’s a magical variation called the Key West Cuban mix sandwich, often adding lettuce, tomatoes, onions, salami, and sometimes even mayo to the equation. Only in the island of Key West will you find this unique twist!  

Now that you’re drooling, here’s where to get the best versions on our sunny little island.  

1. Cuban Coffee Queen  

Known for its iconic café con leche, Cuban Coffee Queen is not just your ultimate coffee stop, but also a go-to for Cuban sandwiches. They’ve even got their own twist—the Cuban Queen Mix, which swaps out pork for chicken, creating a lighter yet equally flavorful combo.  

With three convenient Key West locations, this is the perfect spot to grab your morning coffee and sandwich before heading off for your day of adventures. It’s an ideal starting point and a local favorite for good reason.  

Look for it: Key Lime Square, Margaret Street, and Clinton Square Mall  

2. El Siboney  

If authenticity is what you’re after, El Siboney is where Cuban food reigns supreme. Tucked away from the bustle, this hidden gem serves up traditional Cuban flavors, from ropa vieja to—of course—stellar Cuban sandwiches.  

Their Cuban sandwiches come with a generous portion of roast pork, and they set the standard for traditional Cuban goodness. Pair it with black beans or yucca fries for the complete experience.  

Look for it: Catherine Street (Old Town) and Stock Island  

3. Sandy’s Café  

If Key West had an MVP for Cuban sandwiches, Sandy’s Cafe would be fighting for first-place votes (and winning hearts). Serving from M&M Laundry on White Street, it’s both quirky and unforgettable—a true “when you know, you know” spot.  

Their award-winning Cuban mix sandwich takes the traditional up a notch with the addition of salami, making it irresistible. Grab yours to-go and enjoy it by the ocean, or sneak it into Mallory Square to watch the famous sunset.  

Look for it: White Street  

4. Frita’s Cuban Burger Café  

Feeling adventurous? Head over to Frita’s Cuban Burger Cafe for a pork burger spin on the Cuban sandwich. Their signature Frita is drizzled with a special sauce that’ll blow your mind. And if you’re in the mood for something lighter, their white Cuban sandwich (made with turkey, chicken, and Alabama white BBQ sauce) is a must-try.  

For an added bonus, treat yourself to one of their thirst-quenching milkshakes while soaking in the nostalgic Key West vibes.  

Look for it: Off Duval Street  

5. Five Brothers Grocery and Sandwich Shop  

Five Brothers is where Key West locals go to satisfy their Cuban cravings. This little spot on Southard Street doubles as a Cuban grocery and deli, serving both the traditional Cuban sandwich and the Key West Cuban mix.  

Insider tip? Grab a sandwich, pick some fresh Cuban toast, and head straight to nearby Fort Zachary Taylor for a picnic with a view. There’s a reason the Green Parrot Bar’s lunchtime crowd often shows up with sandwiches from here!  

Look for it: Southard Street  

6. Anna’s Cuban Café  

Spice lovers, this one’s for you. Anna’s Cuban Café is the proud home of the spicy Cuban, made with pickled jalapeños and habanero mayo. If that’s too fiery, don’t worry—their classic options are equally fantastic.  

With outside seating on South Street, this laid-back casual restaurant pairs perfectly with sunny Key West afternoons.  

Look for it: South Street  

7. El Meson de Pepe  

Located by Mallory Square, El Meson de Pepe offers not just incredible Cuban sandwiches, but a slice of maritime history, too. Their sandwich perfectly captures the flavor of Cuba while keeping the island of Key West charm alive.  

While you’re there, explore their full menu of authentic Cuban dishes. Or, simply sip on a mojito and soak up the upbeat music as the evening Key West crowd comes to life.  

Look for it: Mallory Square  

Why Stop with Just One Sandwich?  

Each stop on this sandwich crawl offers a unique experience, from the different versions of Cuban sandwiches at Five Brothers and Frita’s, to the authentic Cuban coffee found at Cuban Coffee Queen. Whether you love the simplicity of the traditional or the hearty additions of the Key West Cuban mix, one thing’s for sure—your taste buds are in for a wild ride.  

Finally, don’t leave Key West without pairing your sandwich with cafe con leche or grabbing a slice of Cuban toast for breakfast. Trust me, it’s the perfect gift for your soul.  

The Cuban Sandwich Crawl  

Add Key West Cuban sandwiches to your foodie bucket list. All you need is an appetite and this guide! From White Street to Mallory Square, the hunt for the best Cuban sandwiches is worth every bite.  

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