THE ABSOLUTE TEN BEST BARS IN THE FLORIDA KEYS
^ Listen to “Raise My Glass To The Upper 48” at every one of the bars listed below, you CAN do that!^
THE ABSOLUTE TEN BEST BARS IN THE FLORIDA KEYS
What makes a great bar? We all may have different opinions on them, but these are my favorites. In my view, the first part of the criteria is the place has to have character. If you’re going to be in a bar in the Keys, it HAS to have that Keys feel, otherwise you might as well stay in Miami, New York, Cincinnati, wherever. History can have a major influence as well. Even in the newer bars listed here, they may be new as a bar, but the structure they are in has been around for a while. We call this the "If The Walls Could Talk" ratings, which many will have. There certainly are places which are pleasant places and nice bars in the Keys, however the places listed here are the stand outs. These bars are head and shoulders above the rest. Additionally, regretfully two of my former absolute favorites, owned by the same individual, are no longer rated. The list is in no particular order. These are all exceptional bars.
THE GREEN PARROT - 601 Whitehead Street, Key West
The Green Parrot has been around since the island was founded.. okay not that long, however it’s been there in various guises and names since 1890. It’s been The Green Parrot for about forty years. Before that it was The Brown Derby, however I don’t know for how long. There’s no food, it’s a bar. Live music is every Friday, Saturday, and Sunday, sometimes in the middle of the week as well. It’s open air, rustic, with large windows always open, not forgetting doors as well. The floor is uneven. The walls and ceiling are draped with pictures and knick knacks. Only negative thing that can be said about the ‘Parrot is that they don’t allow dogs. Pool table and two streaming web cams. “If The Walls Could Talk” Rating 10+
THE CARIBBEAN CLUB - MM 104 Bayside, Key Largo
The Caribbean Club is an incredible bar, very much like The Green Parrot, only with a spectacular view of Blackwater Sound as its backyard. Built in the 1938 as a fishing camp, nine years later the Bogart/Bacall movie “Key Largo” was filmed there. Another bar where it’s a bar only, there’s no food. Dogs welcome. Fireplaces on either end get use in the winter months. Live music at night, closes at 4am. “If The Walls Could Talk Rating” 10+
CAPTAIN TONY’S SALOON – 423 Greene St, Key West
Without doubt, the most fascinating bar in the Keys. Captain Tony’s, as far back as I have traced, started life as an ice house back in the early 1800’s. There is also a grave of a woman in the pool room who, legend has it, was hung on the hanging tree, which is on the other side of the bar. I don’t know how many people were hung on the tree, but she wasn’t alone. During prohibition it was a speak easy called “The Blind Pig” owned by a man named Joe “Josie” Russell, who, when a bank would not cash a $1000.00 check for Ernest Hemingway, who just moved to town, Russell did. Quite a sum in those days! Russell and Hemingway became fast friends and often would sail to Havana (rum smuggling perhaps? It was a speakeasy after all!) and hung out at a place called Sloppy Joe’s there. When prohibition was repealed, the Blind Pig went legit and took the Havana bar’s name, as it fit Russell’s. Hence, Sloppy Joe’s was born! Ernest and Josie would hang out there daily in the afternoon between when Hemingway moved to Key West in 1929 and when Russell did not renew the lease in 1937. During this stint, Hemingway also met his future third wife, Martha Gelhorn there, who apparently made a point of it. Hemingway left Key West in 1939 with Gelhorn and headed to Cuba. Some years later, a man who came to Key West fleeing the mob in New Jersey, only to become a fishing captain, Tony Toracino . The bar was then named “Captain Tony’s Saloon” and Captain Tony later also became mayor of Key West. He was a known romantic with the ladies and a notorious philosopher of all things good. Additionally he was also a major supporter of Jimmy Buffett and actively encouraged him to play his own songs in the bar. Hopefully one day they will encourage songwriters again with the enthusiasm Captain Tony did, though you will hear some, snuck in between the cover songs.
The place itself is wallpapered with business cards stapled to the walls, from ten minutes ago to fifty something years back, maybe more. Additionally, braziers hang from the ceiling and various license plates pepper what free space is on the walls. The ladies room is said to be haunted, but it may very well be the whole place. Live music all day and night long, as well. Dogs are welcome until 5pm. . “If The Walls Could Talk Rating” 10,000+!!!
Sharkey’s Pub and Galley - 522 Caribbean Dr. Key Largo
Sharkey’s is tough to find, but well worth it. Located off the beaten path of Overseas Highway, down a street or two and on a canal in Key Largo, Sharkey’s is a wonderful local’s place that serves food and also offers live music. It’s one of those out of the way places that is a treasure and deserves to be checked out and enjoyed. Additionally, a respectable selection of craft brews on hand and a full bar. Live music at night as well. “If The Walls Could Talk” Rating .. mostly an outdoors affair so there are no walls, per say, though under cover: 4.
SMOKIN TUNA SALOON - Charles Street, Key West
Charlie Bauer, Scott Kirby, and partners opened Smokin’ Tuna nearly two years ago in the former El Alamo location, which is actually quite a large complex. Charlie has applied his nearly twenty years’ experience in starting and running The Hog’s Breath Saloon and making it the success that it’s become. The Smokin’ Tuna has quickly gone the route of becoming the nucleus for being Key West’s go to spot for music. When the question arises “Hey, do you know who’s playing in town tonigfht?” and the answer is “No”, the subsequent reply is “Well let’s go to Smokin’ Tuna, they always have something good happening!” Open air, but cover is available in the event of rain.
The Cork and Stogie - 1218 Duval St. Key West
The Cork and Stogie isn’t really a bar per say actually. The simple fact of the matter here is that it is a charming place that serves craft beer and wine. It is literally a “Mom and Pop” place with a quaint, warm atmosphere hosted by owners Dave and Leslie, along with their son, Dave Jr. They have a regular local crowd and also get their fair share of folks visiting town. Dogs are allowed outside on the porch and patio. There’s often food in the late afternoon/early evening as well. Great, laid back, easy going atmosphere!
The Dockside Bar - 35 Sombrero Blvd. (MM49) Marathon
It’s pretty damn hard to beat a bar on a marina and the Dockside Bar at Sombrero Marina is the personification of that statement. The Dockside Bar is located on the road directly behind the Publix in Marathon (Sombrero Blvd.) about a quarter mile down. Covered seating outside, with a stage, as well as an inside bar, it overlooks the Sombrero Marina at Boot Key. They have live music and a very cool, casual, local atmosphere. They were doing some renovations there when I was by last January. Whenever I see historic places getting renovations, I get worried. I haven’t been back since, so I have my fingers crossed that it hasn’t lost its funkeyness. Bars like The Green Parrot, The Caribbean Club, and The Dockside Bar all have a fantastic uniqueness that’s a rustic Keys “joint” that really can’t be beat. Fingers crossed.
Schooner Wharf – Corner of William and Lazy Lane, Key West
Charles Kuralt said “The world revolves around the Schooner Wharf Bar” and who would argue that? Schooner Wharf is a Key West staple! Here’s a bar that sits on a Marina, plus throw in that Key West legend and icon Michael McCloud, who plays there five days a week, so what more could anyone ask? Schooner’s has a full bar, a web cam, outstanding staff, live music, incredible view and atmosphere, and always a great crowd. They also sponsor several events, such as the January – April Wrecker’s Races, plus the dropping of the wench (the owner Evalina) off a yard arm docked next to the bar for New Years… among other fun stuff! Dogs are not only allowed, but encouraged! “If the Walls Could Talk Rating”: Half of Schooner’s is outside, the inside walls and ceiling however warrant an 8.
The Porch - Duval and Caroline St., in the Porter Mansion
When Chris Schultz started The Porch a couple of years ago, I doubt he realized that he’d just started a craft beer revolution in Key West since then!The Krawl, 2 Cents, The Cork and Stogie, Shots and Giggles, World of Beers, have all either opened, or started carrying craft brews since The Porch started the trend. Plus, there are more on the way. There is the former Waterfront Market, which Schultz is turning into the Waterfront Brewery. In addition t that, there is another brew pub under construction on Eaton St. next to the restaurant store. The Porch carries only craft beer and wine and is located inside the Porter Mansion, which dates from the 1840’s. Craft beer is the main focus with well over 150 available from both the U.S. and around the world. They also have a very respectable wine selection available. A great staff, plus it’s said to be haunted by a friendly ghost who moves things around in the off hours. The atmosphere is incredible in the antique home, with ceilings I would guess between ten and twelve feet high. Seating at the bar is about eight or nine, with additional seating in the attached room extension. With a name like “The Porch”, there is obviously seating outside on the grand veranda out front, where you can watch the world walking by on their Duval St. quests. “If the Walls Could Talk Rating”: At one point, they just might! 10
SMUGGLER’S COVE - MM 85.5 Islamorada
Smuggler’s Cove has everything you’d need to survive in a perfect classic Keys setting. It’s an old, classic keys bar on a small marina. It’s quiet, easy, laid back in the afternoon. The personification of what you’d expect in the mind’s eye of what hanging out in a bar on a marina in the Keys, is all about. They also have live music Friday and Saturday nights. In addition, there’s a motel in the event you just want to stay. Laid back, in the Keys? This is it! “If the Walls Could Talk Rating” 7
ALABAMA JACK’S - Card Sound Rd. Card Sound/Key Largo
Alabama Jack’s has had the same band playing there every weekend for twenty eight years. The Card Sound Machine started there twenty eight years ago and every weekend afternoon has the place hoppin’ and cloggin’ to the sounds of good ol’ Country music. It’s consistent! Alabama Jack’s is way, way, off the beaten path, unless you’re going to the Keys by way of Card Sound Rd. in which case it’s twelve miles from Rt. 1. Located in the middle of nowhere, at the base of the Card Sound Bridge, it was started I believe in the late forties or early fifties. It’s been in movies, it’s been written about in books, plus there may be a song or two about it as well. There’s a corrugated tin roof, however there are no walls and it sits on a canal, where the occasional American crocodile meanders by. It has that wonderful Keys rustic feel to it that can’t be replaced or replicated by newer or remodeled places. Many say they have the finest conch fritters in the Keys. This is also pretty much a day place as they close somewhere around sunset. Without question, the best time to go is the weekend. “If The Walls Could Talk Rating” .. there are no walls!
So there you have it! From Key Largo to Key West, the ten best!
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