If there’s one food that sparks an argument in Key West almost as quickly as asking where the best sunset is, it’s the Cuban sandwich.
Mention your favorite at a local bar, and someone will immediately tell you you’re wrong.
Honestly? That’s part of the fun.
The Florida Keys have their own take on the Cuban sandwich. While Miami purists might insist there’s only one “correct” version, Key West has always done things a little differently. Around here, you’ll often find lettuce, tomato, mayonnaise, and sometimes even salami making their way onto a Cuban Mix. It’s a little messy, a little controversial, and absolutely delicious.
I’ve eaten more Cuban sandwiches than I’d probably admit to my doctor, and after years of running charters around Key West, guests ask me all the time where they should go after getting off the boat.
So here’s my list.
Sandy's Café – Captain Zak's Favorite
If you only have time for one Cuban sandwich in Key West, this is where I’d send you.
Not because it’s fancy.
Actually, it’s the complete opposite.
Sandy’s sits beside a laundromat on White Street. You walk up to a little service window, order your sandwich, grab a café con leche, and wait while it comes off the press.
It doesn’t look like somewhere that would make one of the island’s most famous sandwiches.
That’s exactly why I love it.
The bread is perfectly toasted, the pork is flavorful without being greasy, and every bite has just the right balance of meat, cheese, pickles, and mustard. If you’re feeling adventurous, order the local-style Cuban Mix with lettuce, tomato, mayo, and salami. It may not make traditionalists happy, but it’s pure Key West. Sandy’s has become one of the island’s most celebrated Cuban sandwich stops and is consistently recommended by both locals and visitors.
My order?
A Cuban sandwich, a café con leche, and about ten minutes sitting outside watching White Street go by.
Sometimes the simple things really are the best.
5 Brothers Key West
If you’ve asked a local where to grab lunch, there’s a good chance they’ve pointed you toward 5 Brothers.
From the outside it looks like a neighborhood convenience store.
Inside?
One of the best sandwich counters on the island.
Their Cuban Mix has developed a loyal following over the years, and for good reason. Everything is made fresh, the portions are generous, and it’s exactly the kind of place locals stop into during the workday.
If you’re staying downtown, this is one of the easiest great Cuban sandwiches to find.
El Siboney Restaurant
Some people come to El Siboney for the ropa vieja.
Others swear by the roast pork.
Me?
I’m never disappointed by their Cuban sandwich.
Unlike some of the quicker walk-up spots, El Siboney serves a more traditional sit-down Cuban meal, making it a great place if you’re traveling with family or simply want to relax over lunch.
Their roast pork is excellent, and it shows up in the sandwich.
While you’re there, order some black beans and rice.
You’ll thank me later.
Cuban Coffee Queen
505 Front Street, Key West, Florida, 33040
Most visitors know Cuban Coffee Queen because of the coffee.
The sandwiches deserve just as much attention.
Their Cuban Mix is consistently one of the most recommended on the island, especially if you’re heading out for a day of sightseeing or catching a boat. It’s quick, portable, and pairs perfectly with a strong Cuban coffee.
There are several locations around Key West, making it one of the easiest quality lunches to grab on the go.
Ana's Cafe and Southernmost Grocery
Sometimes the best meals aren’t the ones with the longest line.
Ana’s has built a loyal following among both locals and repeat visitors. Their Cuban sandwich is simple, fresh, and consistently well-made.
If you’re staying near the Southernmost Point or spending the day on that end of Duval Street, it’s an easy stop that often flies under the radar.
Several locals consider it one of the island’s best-kept lunch spots.
Honorable Mention: Deluna's Café at Boyd's Campground
Technically, this one’s over on Stock Island.
It’s also absolutely worth mentioning.
Deluna’s Café is tucked inside Boyd’s Key West Campground, and if you didn’t know it was there, you’d probably drive right past it.
That would be a mistake.
Their Cuban sandwich is outstanding, and everything else coming out of the kitchen is just as impressive. It’s one of those places that feels like you’ve discovered a local secret.
If you’re staying at Boyd’s—or even driving through Stock Island before heading into Key West—stop in; you’ll be glad you did.
So…Who Really Has the Best Cuban Sandwich?
Honestly?
You could ask twenty locals and probably get twenty different answers.
That’s part of what makes Key West such a fun food town.
But if you asked me while we were cruising back from the sandbar and I could only recommend one place, I’d point you toward Sandy’s Café on White Street every single time.
There’s just something about ordering a Cuban sandwich from a tiny walk-up window next to a laundromat that feels perfectly Key West.
Hungry After Your Charter?
One thing I’ve noticed over the years is that everyone steps off the boat hungry.
After a day spent snorkeling, exploring the backcountry, or relaxing at the sandbar, a great Cuban sandwich somehow tastes even better.
If you’re joining us aboard a private charter with Casual Monday Charters, ask your captain where they’re grabbing lunch after work.
There’s a pretty good chance one of these places is at the top of the list.
