The Florida Keys: Escaping to this archipelago has been a longstanding American tradition, and one look at the colorful colonial houses and casual beach shacks peeping out from the lush vegetation is enough to show you why. The islands are mainstays for artists, fishermen, nature conservationists, and, of course, tourists — all of whom love to chill out and enjoy a laidback drink, making dive bars an essential Florida Key feature.
Unless you’re flying into Key West International or sailing in on a cruise ship, you’ll drive the 112 miles off of mainland Florida on a grueling (we’re not going to lie) trip down U.S. Highway 1, most of which is one lane. Trust us, frequent breaks and pit stops are the only way to keep your sanity in check and the only way to start your vacation off on the proper, flip-flopped foot (not primal screaming behind a delivery truck for over an hour).
As you race off the mainland, you’ll notice a few reoccurring themes: sunshine, unpretentious locals, fishing (you are surrounded by water, after all), and the unspoken mutual respect of a casual cool atmosphere.
Welcome to the Conch Republic: relax, take your time, and don’t be afraid to venture off the pavement onto the dusty sand roads — you’ll be surprised at what you’ll find. So, whether you’re closer to mile marker 0 or 112, we have the best places to pull off and let the world melt away. In order of mile marker, here are the Keys’ can’t-miss watering holes.
License plates and fishing paraphernalia cover the walls of this institution that has been holding the fort down since 1947. Frequented by recreational fisherman, Harley bikers, and anyone starting the trek down the Overseas Highway, stop here for solid bar grub, eccentric company, and a cold one.
Set on the water with driftwood walls and patches of glass on the floor that give patrons a peek below deck at crystal-clear green water, the Pilot House is known for its solid seafood (both fried and fresh) as well as a bar menu that will make everyone happy (colorful, tropical mixed drinks are not only offered, but encouraged). The décor proves just as colorful with a sign that reads: “Drink till he’s cute.” What happens in the Keys, stays in the Keys.
Follow the dusty sand drive down to the water where you’ll find sun-bleached picnic tables and matching docks jutting out into the sound providing unobstructed views of the endless water and one of the best places (besides Key West itself) to see the sunset. Rich history (it’s world-famous…but you’ll have to visit to truly understand why!), good food, and stiff drinks are just some of the reasons to stop by and visit.
Located on the sweet escape of Islamorada, Hog Heaven provides a relaxed contrast to some of the finer/upscale locations on the island. As the name suggests, the place is frequented by motorcyclists, passersby, and locals looking for a chill scene. Dine and drink in the shade or hang out on the docks under the umbrellas — either way, you’re in for a barfly’s dream come true.
Decorated in dollar bills and surrounded by docks where you’ll find dancing tarpon, this outdoor bar features sun, fresh food, and a “shoes optional” sort of attitude. The dusty sandlot where it’s located plays home to vendors selling straw hats, sunglasses, fun painted signs, and wooden parrots (you know, typical Keys stuff). Arrive by boat, car, or jet ski to relax with a frozen beverage and chow on the fresh food. Just remember: don’t feed the pelicans.
If you love mingling with locals, don’t drive another mile! Located in the K-Mart plaza (sort of the ultimate indication of a dive bar, no?) this liquor store/bar is perfect for stoping off quickly or for staying awhile. This is as chill as it gets.
Would a bar by any other name be as awesome? No, probably not. If you’re driving through to the southern Keys, No Name Pub occurs at the perfect time for a pit stop. To put it simply, this place is money… seriously, dollar bills hang from the ceiling and line the walls (make sure to ask for markers to decorate your own to make your mark). If you happen to sit outside, keep your eyes out for the native Key deer that congregate. Like common Keys dive bar culture, the menu is packed with fried pub favorites and fresh seafood (when the ceviche is on the “specials” menu, pounce!) and the service is notably amazing. It’s even Zagat-rated — enough said.
Sure, there are no dollar bills hanging from the ceiling or driftwood covering the walls, and the place looks like it’s been vacuumed in the past year, but that does't mean it doesn’t count as a dive bar… have some good clean fun! Whether you sail, drive, bike, or row here, the drinks are classic and stiff, and the food is excellent. You can even bring your own catch and the chef will prepare it!
If there is only one reason to visit Mangrove Mama’s, it’s for the Key lime pie, but pie is not the only thing that makes Mama’s great. This chill bar is clean, but not pretentious. The food is top-notch (two words: lobster Reuben) and Mama’s drinks are classic and tropical, delicious, and strong. This place is totally worth the right turn heading south, because, you know, carpe diem!
Ever hear that expression: “small but effective”? That basically sums up Smallest Bar. On Duval Street among the large-bar institutions, Smallest holds its own; located in the Old Customs House, the walls are spray-painted with tropical scenes that lay just a few blocks away while the bar seats just two to three at most. Here, intimate is not a dirty word. If you’re feeling retro, grab the drink in a pineapple and enjoy a solid menu of well-made tropical drinks that keeps this tiny place on the map.
If building your own Bloody Mary isn’t enough to get you visiting the Green Parrot, then the location will: it’s known as “The first and last bar on U.S. 1.” Anything goes under the “big top” bar where live music, pool games, pets, and random parties of locals spilling out onto the street are all commonplace. Enjoy the mixed frozen drinks or the great selection of beer on tap. Can’t find the place? Look for the glowing green light.