When you’re dining in the Florida Keys, a series of tropical islands off the state’s southern tip, it’s pretty much a no-brainer that you’ll want to make the most of their waterside locale and perennial vacation atmosphere when you plan your activities. And that includes your dining experiences. What could be better than a delicious meal and drink (with or without an umbrella) with sides of balmy breezes and nearby Gulf, bay, or Everglades vistas? And throw in a serving of blazing sunset and you’ve got a meal fit for, well, an expert traveler. The places below, reps of both Old Florida and new deliver all these things and more with their original takes on Florida specialties and rare waterfront locations.

Don’t leave this mind-blowing part of the world without giving these restaurants and bars—and the dishes they’re most known for—a try. Seriously.


Coopertown Airboats, a premier guided tour company offering airboat adventures in one of the nation’s most incredible natural environments—the Everglades—knows a thing or two about the waters around these parts and the creatures that inhabit them. Take a 9-mile airboat tour with your family and besties to see and learn all about them—you’ll remember it for the rest of your life! Then refuel on some of the area’s most characteristic delicacies served at the outfit’s very unassuming Coopertown Restaurant & Giftshop. Snap the dishes before digging in and then post to your fave social channels. ‘Cause who wouldn’t ‘like’ the frog legs, gator tail, and catfish you chow down on? Nothing says ‘taste of Florida’ quite like these fresh catches served in a downhome country style in a rustic Old Florida (the company’s been operating for 45 years) building.

For another Florida shack that serves unique foods and puts on zero airs—really, it couldn’t be any more down-to-earth—aim for Alabama Jack’s on Card Sound Road (aka County Road 905A). Resting on a pair of barges in the mangroves, this dive bar is open-air, right on the open water and, much like its house band (The Card Sound Machine), which has been playing here for more than a generation, it never misses a beat.

In addition to the motley crowd of locals and other fun-loving patrons you’ll find here (not to mention motorcycles, which are the measure of any bar on the water worth its salt, or saltlessness), you’ll experience Florida friendliness at its best (yep, that’s a thing, even if you’ve never heard the term). The burgers and steamed shrimp are dope, but the dish that really slays is the Conch Fritters—tropical pancake-like bites loaded with conch. Down them with a margarita or a cold beer and feed on the energy, too.

Key Largo

Natural aquarium bar is unique to the Pilot House

Are you a fan of the Netflix series, Bloodline? Well, Pilot House is one of the star restaurants in this show and it was also featured on Food Network’s Diners, Drive-ins & Dives. For good reason: Few places say Key Largo more than this landmark—a signature dining destination since the ‘50s, located in the downtown area, right on Lake Largo. It has a super cas vibe and marina and manatee views from a covered outdoor patio. You’ll swear the creatures are dancing to the live music.

Oh, and let’s not forget the menu, which showcases some of the best seafood dishes the Florida Keys have to offer, along with weekly specials, prime rib Thursdays and a mouthwatering Sunday Brunch. You get the picture—there are tons of options. And when it comes to drinks, sure, you can order your favorite cocktail and great wines, but we suggest taking a ‘when in Rome’ approach…. Meaning, since you’re in Key Largo, sip a cold one from Florida. The local Florida Keys beers at Pilot House make for a perfect accompaniment to the sandwich Diners, Drive-ins & Dives touted on their ‘Succulent Sandwiches’ episode—the Harvey Fish Sandwich. Order it—and then give your dining adventure a sweet ending with a serving of key lime pie.

But don’t stop there! Key Largo is also home to the uber-gourmet Bayside Grille and Sunset Bar on Florida Bay—the water and sunset views will knock your flippers off, but your grams will face stiff competition. The elevated indoor dining room offers panoramic vistas along with a thoroughly island (Keyribbean, that is) atmosphere and menu—the locally caught seafood dishes and angus steaks are to drool for. An open kitchen gives you a glimpse of the bustling prep of yum entrees like Keyribbean Lobster Tail and Seafood Enchiladas.

The Sunset Bar, just below the restaurant, puts the outdoor setting, more Keyribbean specialties, and live music front and center. Every perch here is a privilege.


outside view of lorelei restaurant over the water


The spectacular sunsets in the Florida Keys deserve the love they get, especially the ones you’ll see at Lorelei Restaurant and Cabana Bar, whose location maximizes the wow factor. The tables here are planted right at the edge of Florida Bay and give westerly views over the water that looks just like the images on souvenir postcards. No wonder the restaurant stages sunset celebrations every single night! Whether you go for one of Lorelei’s outstanding seafood catches of the day, their Surf & Turf, or Lemon Caper Chicken entrée, two undeniable truths remain—there’s plenty more beyond those options and everything tastes better with an Islamorada sunset and live tunes in the background.

Just so you know though, the daytime dining here is also great (think: deep blue skies and waters). Come for breakfast on the bay and sip a Bloody Mary with your Three-Egg Omelette, Short Stack or Shrimp & Grits.

Marathon & The Lower Keys

Calling all lobster lovers: Dash over to Keys Fisheries Restaurant on Marathon’s commercial fishing dock on the edge of Florida Bay and order the Lobster Reuben it’s sooo famous for. Yep—we said lobster reuben (forget the corned beef, guys—you’re in the Keys now!) Maybe it’s because Keys Fisheries is also a seafood market that sells unbelievable Florida Keys seafood, but you’ll be hard-pressed to sample something fresher and tastier than the reuben.

No need to limit yourself to that specific culinary invention, of course. Folks come by land and sea (there’s an on-site marina) to sample any number of seafood specialties here, from the Hog Fish Francaise to the Key West Shrimp to the Conch Chowder. They’ll even cook your own catch.

If you’re bad with names but can never forget a great meal and love funky off-the-beaten-track hangouts with crazy pasts, then No Name Pub in Big Pine Key is your place. It may be isolated and a bit hard to find (hint: it’s across from Bogie Channel and there’s water near those colorful outdoor picnic-style tables and umbrellas), but Zagat has rated it the ‘Best casual dining experience in the Florida Keys” and heartily recommended their pizza, chili, smoked fish dip, and sandwiches. Actually, you can’t go wrong with anything on the menu—it’s all good! As for the crazy history aspect: The upstairs featured a brothel back in the 30s—it didn’t last long. There are still things to buy in addition to the fab food and drink, but they come in the form of souvenirs, like T-shirts, hats, and can koozies emblazoned with their logo. Grab some—there’s just something about that name (wait…no name).

Key West

stools and tables on an outside deck at a Key West restaurant

Key lime desserts rock in the Keys. It’s worth sampling as many versions as you can when you visit. But the oh-so-tropical Stock Rock Cafe’s claims to sweet fame have nothing to do with those treats—it’s the irresistible soft-serve ice creams they dish out in their ice cream shop. Also, the waterfront restaurant’s dishes like fish tacos, Kickin Chicken Sandwich, and B.S. Burger (uh-huh, the B.S. stands for Bull Shit ‘cause the names of the dishes are as awesome as their flavors). Oh—and the beer bar’s regional craft beers, too.

And did we mention the manatees? With a prime location right on Cow Key Marina overlooking crystal clear waters known for manatee action, Stock Rock Cafe all but guarantees sightings. They’ve even named the manatees that hang out here. Say hello to Marshal, Big Moe, Speedy, Pete, Otto, and Little Rich (that is rich—he weighs 900 lbs.)

Hey, you’ll want to hang at this chill spot, too. Over and over again. And the dock welcomes you whether you come by boat or car.