Let’s be honest—planning dinner in Key West is like trying to pick your favorite Jimmy Buffett song. There are just too many good options, and you’re probably going to end up a little tipsy either way.
This tiny 4.2-square-mile island packs more culinary punch than a hurricane hitting the Florida Keys. We’re talking 300+ bars and restaurants crammed into a space smaller than most college campuses. From waterfront views that’ll make your Instagram followers weep with envy to Cuban food so authentic you’ll forget you’re still in the United States, Key West is a foodie’s paradise wrapped in tropical fruit and served with a side of live entertainment.
Whether you’re celebrating an anniversary, trying to impress someone special, or just want to eat something more exciting than hotel continental breakfast, this guide has you covered. I’m talking fine dining restaurants with dress codes, dive bars where flip-flops are formal wear, and everything in between. From the historic seaport to the heart of Old Town, these are the spots that’ll make your Key West dinner experience unforgettable.
Ready to eat your way through paradise? Let’s dive in.
Fine Dining with Views That’ll Ruin You Forever
Sometimes you want to get fancy. Like, really fancy. These spots bring the romance, the ambiance, and the kind of waterfront views that make you seriously consider selling everything and becoming a professional beach bum.
Latitudes: The Ferry Ride Worth Taking
Here’s the thing about Latitudes—you have to work for it. This fine dining restaurant sits on Sunset Key, which means you’re taking a 5-minute ferry ride to get there. But trust me, that little boat ride is just building anticipation for what’s about to be an epic dining experience.
They’re famous for their seared scallops (which pair beautifully with tropical fruit and fresh fish), and the romantic ambiance is off the charts. Fair warning: there’s a dress code, so save the flip-flops for another night. The attentive service and waterfront view make this a must-visit for special occasions.
Louie’s Backyard: Where the Atlantic Ocean Steals the Show
Located near the Southernmost Point, Louie’s Backyard offers oceanfront dining that’s both upscale and refreshingly relaxed. This local favorite has mastered the art of the outdoor eatery—you get all the fancy without feeling stuffy.
Their cocktails are legendary, and watching the Atlantic Ocean from their deck while sipping something tropical is basically mandatory. Pro tip: if you’re not ready for the full dinner commitment, their bar seating still gets you those killer views.
Hot Tin Roof: Mallory Square Magic
Perched in the Ocean Key Resort facing Mallory Square, Hot Tin Roof serves up what they call “Floribbean” cuisine—that’s Florida meets Caribbean, and yes, it’s as delicious as it sounds. Their chef-driven menu features standouts like crab cake Benedict with key lime honey glazes that’ll make you question why you ever ate breakfast anywhere else.
The live entertainment and great cocktails don’t hurt either. Plus, their Sunday brunch is worth planning your entire weekend around.
A&B Lobster House: Old School Elegance
This high-end dining spot sits in a historic building with a harbor-facing balcony that screams “special occasion.” They’re best known for their spiny lobster (obviously) and filet mignon, plus an extensive wine list that’ll make wine snobs weep tears of joy.
It’s one of those iconic Key West restaurants where the lobster rolls are legendary and the waterfront view never gets old.
Iconic Key West Eats You Can’t Skip
These are the “don’t even think about leaving the island without eating here” places. The spots that locals recommend and tourists remember forever.
Blue Heaven: Chaos, Chickens, and Culinary Perfection
If Key West had a mascot restaurant, it would be Blue Heaven. Located in historic Bahama Village, this place is pure island magic—and by magic, I mean there are actual chickens and roosters wandering around while you eat.
Their Jamaican jerk chicken is incredible, but honestly, everything on their menu hits different when you’re eating it surrounded by Key West’s most charming chaos. They accept dinner reservations, but brunch is walk-in only (and worth the wait). Grab a cocktail at their sister spot across the street while you wait—it’s all part of the experience.
The live music and favorite dishes make this a perfect spot for your first night in town.
Conch Republic Seafood Company: Happy Hour Heroes
Located in the historic seaport in what used to be an old ice plant, Conch Republic has mastered the art of casual waterfront dining. Their conch fritters are legendary, but here’s the insider tip: ask for the off-menu Key West Reds—these shrimp taste more like lobster and are absolutely worth it.
Their happy hour is buy-one-get-one at the bar, and you get a token you can save for later. I’m not saying I have a collection of these tokens, but I’m not not saying that either.
B.O.’s Fish Wagon: Dive Bar Perfection
This legendary local restaurant has exactly zero frills, and that’s exactly the point. Famous for their fried fish sandwiches and funky vibe, B.O.’s is where you go when you want good food without any pretense.
Show up in shorts and flip-flops, grab a picnic table, and prepare for one of the most authentically Key West meals you’ll ever have. It’s a fun place that perfectly captures the island’s “whatever, we’re in paradise” attitude.
Matt’s Stock Island Kitchen & Bar: Worth the Short Trip
Just off Key West on Stock Island, Matt’s offers a great spot for comfort food with their “hook and cook” local fish options. Their bottomless brunch menu and bloody Mary bar make this outdoor eatery a local favorite.
It’s a bit off the beaten path, but if you want to escape the Duval Street crowds while still getting amazing food, this is your spot.
Eaton Street Seafood Market: Gas Station Turned Gourmet
This vintage gas station turned seafood paradise is one of the best places for fresh catch cooked exactly how you want it. Their lobster rolls and fried conch are perfection, and you can eat in or take your fresh seafood to go.
The staff here knows their stuff—if you caught something on a charter and have no idea how to cook it, they’ll walk you through it.
Looking for more ideas on where to eat? Check this out!
Cuban Flavors That’ll Transport You
Remember, Key West is just 90 miles from Cuba, and you can absolutely taste that influence throughout the island.
El Siboney: No-Frills Cuban Authenticity
This Cuban food spot off Duval is where locals go when they’re craving the real deal. Their ropa vieja is incredible, and the black beans are some of the best you’ll find anywhere.
Fair warning: the portions are huge. Like, “definitely sharing this or taking half home” huge. But the prices are reasonable, and the good food is consistently excellent.
El Meson de Pepe: Salsa Music and Cuban Sandwiches
Near Mallory Square, El Meson de Pepe brings the party with live entertainment and a festive vibe. Their mojitos are dangerous (in the best way), and their Cuban sandwiches hit all the right notes.
The live music makes this a great spot for dinner with entertainment built right in.
Amigos Tortilla Bar: The Square Taco Revolution
Okay, hear me out—square tacos. They claim scientifically that square tacos hold more stuff than regular tacos, and honestly, I’m not arguing with science. Located near Duval Street and Sloppy Joe’s, this casual spot serves fresh seafood in those genius square tortillas.
The people-watching from their patio is premium entertainment, and their margaritas don’t hurt either.
Small Plates, Big Flavors
Sometimes you want to graze, share, and make dinner last all evening. These spots are perfect for that.
Santiago’s Bodega: Tapas and Good Times
This small plates and wine bar is perfect for groups who can’t agree on just one dish. Their goat cheese shrimp and saganaki are standouts, and the cozy ambiance makes conversation flow as smoothly as their wine.
Reservations are definitely recommended—this place fills up fast, and for good reason.
Café Marquesa: Intimate Fine Dining
With only 50 seats, this intimate dining room creates an automatically exclusive experience. They’re known for seasonal menus that take advantage of what’s fresh, plus homemade breads and standout cocktails.
The entire menu changes regularly, so you’re always in for something new. The attentive service and citrus beurre blanc preparations make this a favorite among serious foodies.
Casual Spots That Still Deliver
Not every great meal requires getting dressed up. Sometimes the best dining experiences happen in flip-flops.
Garbo’s Grill: Korean BBQ Meets Key West
This food truck tucked behind Hank’s Hair of the Dog is a Key West institution. Their Korean BBQ tacos are exactly the kind of fusion that shouldn’t work but absolutely does.
The chill vibe, live entertainment, and the fact that you can wander into Hank’s for drinks make this a perfect casual dinner spot.
DJ’s Clam Shack: TV Fame for Good Reason
Featured on Diners, Drive-Ins and Dives, DJ’s serves up Northeast meets South cuisine right on Duval Street. Their Maine-style lobster rolls sit alongside mahi tacos and conch fritters.
You can people-watch from their front seating or retreat to the back for a quieter meal. Either way, you’re getting good food with zero pretense.
Caroline’s Café: Duval Street Classic
This bustling location serves classic island eats like po’boys and Cajun chicken. It’s always busy (which tells you something), and the people-watching opportunities are unmatched.
It’s not the fanciest spot on this list, but it’s convenient, fun, and consistently delivers.
Breakfast and Brunch Worth Waking Up For
Dinner not your thing? These breakfast and brunch spots will start your day right.
La Grignote brings French bakery vibes to the heart of Old Town with fresh fruit, croissants, and French toast that’ll make you question why you ever ate cereal for breakfast.
Banana Café, right next door, specializes in crepes—both savory and sweet—plus they serve key lime pie that rivals the best Key lime pies on the island.
Cuban Coffee Queen has three locations and serves breakfast sandwiches that’ll cure any breakfast hangover. Their café con leche is the perfect way to start any Key West morning.
Two Friends Patio Restaurant is famous for their signature bloody Mary and offers live entertainment throughout the day. It’s the kind of place where breakfast can easily turn into an all-day affair.
Planning Your Key West Food Adventure
With over 300 options packed into this tiny island paradise, you really can’t go wrong. But if I had to narrow it down to the absolute must-tries for dinner, here are my top picks:
For Special Occasions: Latitudes and Café Marquesa
For Iconic Key West Vibes: Blue Heaven and Bo’s Fish Wagon
For Cuban Flavors: El Siboney
For Casual Excellence: Garbo’s Grill and DJ’s Clam Shack
For Tapas and Wine: Santiago’s Bodega
The beauty of Key West dining isn’t just the incredible food—it’s the whole experience. Whether you’re watching the sunset from a waterfront restaurant, listening to live music while you eat, or sharing tapas with friends, every meal here comes with a side of island magic.
Pro tip: Make reservations where possible, especially during peak season. And remember, this is Key West—even the fanciest places have a laid-back island vibe. So relax, order another drink, and enjoy the fact that you’re eating amazing food in one of the most beautiful places in the United States.
Ready to Eat Your Way Through Paradise?
Key West isn’t just a destination—it’s a culinary adventure waiting to happen. From fine dining restaurants with million-dollar views to dive bars serving the best fish sandwiches you’ve ever had, every meal here tells a story.
The hardest part isn’t finding good food in Key West—it’s choosing where to eat next. Whether you’re craving fresh seafood, authentic Cuban food, or just want to sit somewhere with a great waterfront view and watch the world go by, this island has you covered.
So pack your appetite (and maybe some stretchy pants), make those dinner reservations, and prepare for some of the best meals of your life. After all, you’re not just dining in Key West—you’re dining in paradise.
