Ah, the Florida Keys. The closest you can get to a Caribbean vacation without having to fly. This wonderful chain of islands stretches from just south of Miami all the way to the Dry Tortugas, although the road will only take you from Key Largo to Key West. This hundred mile stretch is full of fun activities like wreck diving and dolphin encounters, and has some great state parks and beaches along the way. The vibe is definitely more “island time” than the rest of the country, and you are sure to have a good time when you visit. Wherever you are in the Keys, you’re never far from a good bar. Whether you stop in for a pint after a full day of diving, or hang out all day sipping margaritas with your feet in the sand, you are sure to find a great place to while away your time in the islands. This is in no way an all-inclusive list, and it’s not meant to be. These are just some of my favorites as you make your way south through the Keys. You should definitely not try and hit all of these in one day, and I always recommend using a designated driver. Also remember there’s only one road, so you could hit a few on the way down and a few on the way back up.

Alabama Jack’s

Dancing at Jack’s on a Saturday Afternoon

Alabama Jack’s is definitely either your first or last stop in the Florida Keys (or both). It sits somewhat off the beaten path as you have to take Card Sound Road to get to it and is literally a hundred feet past the “Welcome to the Florida Keys” sign. This is a great little waterfront dive-bar in the midst of a mangrove swamp. You don’t get sweeping views out to sea, but you can sit and watch the boats go in and out on the channel. The beer is super cold, and their conch fritters are among the best to be found anywhere in the Keys. Regular live music will get your toes tapping and warm you up for the drive south. This place is great for a quick stop or you could easily while away the afternoon there. No Keys pub crawl would be complete without a stop at Jack’s.

Caribbean Club

Humphrey Bogart Was Here

Caribbean Club is the oldest bar in the upper keys, and one of the most storied. Opened in 1938 by real estate promoter Karl Fisher, it was once part of a larger fishing camp. The hotel burned down under mysterious circumstances long ago. Caribbean Club served as both the inspiration and filming location for the 1947 classic Key Largo starring Humphrey Bogart and Lauren Bacall. More recently it served as the filming location for the Netflix original series Bloodline. Caribbean Club is a great little divey bar with a pool table and an awesome view out over the bay. If you’re looking for somewhere to watch the sunset in Key Largo, look no further than this Keys classic.

Hog Heaven

Hog Heaven Across the Lagoon

Hog Heaven is one of my absolute favorite waterfront bars not just in the Keys, but in the country. Located just over the bridge into Islamorada, this is a great place to cap off a long day of exploring the islands. The outdoor part of Hog Heaven is situated around a beautiful lagoon full of fish. There are tables out on the dock or you can sit at the nice long bar. The dock leads out to “Hog Island” which has a picnic table and a fantastic view of the sunset. After the sun goes down, the live music starts on the floating stage out in the lagoon. The underwater lights come on making for a beautiful evening venue. The food is good, the staff is friendly and a good time is sure to be had at this Islamorada classic that’s open until 4AM. There’s also an indoor bar if you’re there in summer and want some air-conditioning or to watch the big game.

Sunset Grille

Let’s Go Down to the Sunset Grille

Just before you get to the Seven Mile Bridge on your way from Marathon to Big Pine Key, take the last left hand turn and wind your way down the road to the Sunset Grille and Raw Bar, right on the water. The outdoor tiki bar and swimming pool make for a wonderful stop on a nice afternoon and the views out towards Bahia Honda are great, especially right around sunset. The bartenders will be happy to whip you up a great island cocktail in a fancy parrot or pineapple glass (or, if you dare, the giant volcano Tsunami or the 48oz. Titanic). Sunday Fun-day, pool parties and a great Happy Hour menu make this another favorite place to while away the afternoon in the Middle-Keys.

No Name Pub

The Name is No Name

This is an old favorite dive bar on Big Pine Key and a classic of the Keys Pub Crawl for many years. It used to be a quaint little local bar a few miles off the main drag and away from the crowds. No longer much of a secret, No Name Pub gets pretty busy on most days. Service isn’t great and the staff seems pretty overwhelmed most of the time, but it’s still a neat little stop. The walls are covered with signed dollar bills from all those who have come before (I’m sure at least one of them has my name on it). This tradition goes back a while to when sailors and fishermen who had an extra dollar would stick it to the wall in case they came back with nothing one day and still wanted a drink. Be sure add yours to the collection while you are there. The bar does have a name - it’s called the No Name Pub in honor of No Name Key which is right across the bridge.

Kiki’s Sandbar

Kiki’s Kickin’ Tuna Nachos

Just across from Big Pine Key on Little Torch Key sits wonderful Kiki’s Sandbar. This brightly colored, sandy, barefoot bar sits right on the water and is not to be missed. The speakers plays Jimmy Buffet and the beach lounge chairs beckon you to stay longer than you had planned. The biggest reason to come to Kiki’s though are the amazing tuna nachos. Fresh ahi tuna on a bed of fried wontons covered in seaweed salad, ginger, wasabi peas and sauce, this is one of the most beautiful and delicious dishes in the Keys. Come for the nachos, kick off your shoes and stay awhile. You didn’t really have anywhere better to be anyway.

Mangrove Mama’s

A Sugarloaf Key Institution

If you’re still hungry, Mangrove Mama’s will give you a good taste of the old Keys and a great taste of local seafood. Some of the best seafood in the Keys at reasonable prices in a bright and cheery island courtyard make Mangrove Mama’s a must-stop at some point during your visit. They also have frequent live music in case you needed another reason to stop in. Mangrove Mama’s is quiet and unassuming compared to a lot of the newer places around, and that’s just how we like it. Come for a drink, stay for a meal, and this is another spot you’ll end up staying way longer than you had planned. Opened in the late seventies, Mangrove Mama’s is a Sugarloaf Key institution.

Sugarloaf Lodge Tiki Bar

Hunter S. Thompson Was Here

If you’re looking for a place to escape the crowds, sit under a thatch roof and chat with the locals, the tiki bar hidden behind Sugarloaf Lodge may be your spot. Tiny and unassuming and right on the water, this is one of my favorite little bars in the Lower Keys. It was one of Hunter S. Thompson’s favorites too. He spent a lot of time at Sugarloaf Lodge over the years and wrote about the antics he got into there on numerous occasions. The beers are cheap and while I always promise myself I’m only stopping here for one, I always end up staying for another. If you need one last stop before pushing on to Key West, this is it.

Green Parrot

A Key West Icon

The Green Parrot is one of two absolute must-visit bars in Key West. They bill themselves as the First and Last Bar on Route 1, and they certainly are. I love this statement from their website: “The Parrot is a jury of non-judging peers, a rugged and ragged council of friends. It is a place of hi-jinks and misadventures, of understated kindnesses, and everyday miracles. It has seen all manner of human exploits, from poetry slams to divorce celebrations, from memorial services to hurricane parties and pet birthday bashes, from tattoo contests to fundraising benefits. The Green Parrot is more than a bar; it is a Key West icon; it is Key West. It has been so many things, to so many people, for so many years. And that spirit will never change.”

The Green Parrot is a great place to relax over a cold beer in the afternoon or to listen to live music in the evening. This place can be packed any time of the day or night, and if you come during Happy Hour you may even see some locals hanging around with their own pet parrots on their shoulders. It’s that kind of place.

Captain Tony’s Saloon

Come See Me, I’ll Be Here

Captain Tony’s Saloon is one of my two favorite bars in the whole country (the other being The Salty Dawg in Homer, Alaska), and is the last stop on this epic Florida Keys pub crawl. Pull up a seat and stay awhile, there isn’t anywhere better to be. The site of the original Sloppy Joe’s, and the go-to bar of Earnest Hemingway, this bar has been open since the repeal of prohibition in 1933. The building’s history stretches back further though. There’s a tree growing right through the middle of it, which used to serve as the town’s “hangin’ tree” where pirates were strung up for all to see. The building has also served as a brothel, a morgue and a cigar factory over the years. When they pulled up some old floorboards during a renovation, several skeletal remains were found, and there are even a few tombstones in the bar. Jimmy Buffet used to play here in his early days and immortalized the place in his song Last Mango in Paris. Despite all of this, Captain Tony’s seems to maintain its busy-but-not-overrun, dive-bar atmosphere year in and year out. It never seems to change. If you ever come and meet me in Key West, I’ll always tell you to meet me at Captain Tony’s.

So there you have it - my favorite spots up and down the Florida Keys. Pick a few the next time you’re making that run, and let me know what you thought. Please don’t try to hit all of these places in one day, and please don’t drink and drive. Cheers!

The View From My Barstool at Hog Heaven in Islamorada