An insider's guide to Key West bars

June 18, 2009 by John - No Comments

Yeah, it’s a fishing site, but into each life a little booze must fall. And what better place to sip a few cold concoctions than sunny Key West, Florida? The name alone evokes a feeling of adventure, escape and, well, debauchery. Those who have been feel its draw long after they’ve left the island behind. Those who have never visited are missing out on a remarkable experience.

At the heart of Key West is Duval Street, a mile-long stretch featuring a wealth of bars, restaurants, cafes, art galleries, and tourist traps of every stripe. Onetime home of pirates, renowned writers and artists, world class anglers, and every type of ne’er do well, latter-day Key West is primarily known for its active (some say overbearing) gay community, laid-back attitude and hedonistic profile. Old timers will tell you that the Duval Street of yore is long gone, and it’s a tough point to contest. I’ve been traveling to Key West since the 1980s, and I’ve seen many of its original establishments fade into obscurity. Look away. But enough charm remains to make it a novel destination that, in many ways, has no peer in the modern world.

If this will be your first trip to the “Conch Republic”, indulge in iconic (and often shamefully commercial) stand-bys like Sloppy Joe’s, Irish Kevin’s, Rick’s/Durty Harry’s, Margaritaville, the Hog’s Breath Saloon, and The Bull. These raucous, must-see bars shouldn’t be missed – they’re all found in roughly the same high-traffic area of Duval. But if you wish to get a better feel for the real Key West (and avoid the ear-splitting music and press of over-heated bodies for a time) try bouncing between the establishments listed below. Note that it’s an evolving list – we’ll be adding new reviews, and editing old ones, after each repeat visit. And we’ve added a few eateries, as well, since eventually one must eat. Of course, we welcome input from our loyal readers. All three of them.

To add to the fun, try to find the items we list under some of the entries as you peruse each new spot. Send us proof that you found them all, and we’ll send you a free Shallowfish tee. Such a deal.

And now, on the the rankings…

THE WONDERFUL

The Green Parrot
601 Whitehead Street
The “Parrot”, a crude Key West gem adorned with the work of local artists, features the best jukebox selection on the island, arguably in the land. A parachute flares across the entirety of the main bar, presumably to help with soft landings. We’re told they have great live music, but on our last three outings to the island we never saw a band. They only accept cash, so go liquid or go without liquids. And they don’t serve food – just cold booze and beer. The bar is dubbed “a Sunny Place for Shady People.” By “sunny”, they mean “sweltering.” The absence of air conditioning makes it a sweatshop in the summer months, though it’s surprisingly comfortable in the evenings and into the night. Of course, senses are generally dulled by that time, which may have something to do with the improved heat tolerance. Personable bartenders cater to a colorful local crowd, but are tourist friendly. Say hello to Beaver, who treated us well. On this latest trip a local on an adjacent stool sat with a beer perched atop his head, from which he took the occasional swig. No explanation offered. When he and his companions settled up, bidding us a polite farewell, he sallied forth into the night with a fresh drink atop his flat pate. At 2 AM, one doesn’t think to ask questions. In short, this quintessential Key West tavern is authentic and timeless.
Find: The Grinch
Extra Credit: Who ran for mayor in 1997?

Louie’s Afterdeck Bar
700 Waddell Avenue
In the heart of every man lies the dream of the perfect waterfront bar. Dream no more. It’s fading rep as a dining establishment aside, Louie’s is still a Key West masterpiece. The restaurant area (inside and out) offers excellent fare and a stellar wine list at staggering prices, and drips with atmosphere. The Afterdeck Bar, however, steals the show with incomparable views of the shimmering Atlantic. Order something chilly, find an empty seat and cast your gaze southward at a painted sky. Aaaaaaahhhhhh. A tip: if you don’t want to drop $250 or more on dinner and a bottle of red, sneak upstairs where a series of flavorful appetizers will suffice as dinner (we highly recommend the Beef Carpaccio, Picollo Fritto and Capicolla Pizza). Then it’s back downstairs for another sip or two under starlight. Divine.

Captain Tony’s Saloon
428 Greene Street
This is the location of the original Sloppy Joe’s where Hemingway spent much of his time drinking Papa Dobles (white rum, lime and grapefruit juice, maraschino juice, blended) and trading epic fish stories – most of them true. In fact, it’s here where the famous writer met his third wife after she paid a 300 lb. bouncer $20 to introduce her. Features the most treacherous floor in the history of bars…all the more frightening in that it must be navigated in semi-darkness. Get your “sea legs” before staggering from room to room. Their present-day bouncer told us he sees patrons “bust ass” nightly on the way to the privies. Forewarned is forearmed. The walls are laden with thousands of business cards, memorabilia of Captain Tony’s colorful life, and more female undergarments than A-Rod’s back seat. (Note to self: frequent Captain Tony’s more often). Check out the (unoccupied) barstools for the names of famous patrons past, including Al Pacino, Robert DeNiro, and Martha Gelhorn, the aforementioned vixen who stole Hemingway’s heart, and who ultimately led him to leave his beloved Key West. Shoot some pool in the recessed game room, pee into the ice-laden urinals, surf the pitched floors with abandon and smell history in the walls. Note that history smells like old sweat and spilled beer.
Find: picture of a young Bob Dylan
Extra credit: Gordon Lightfoot

Sunset Pier
0 Duval Street
Yeah, it’s a cliché on pilings, and not a great fit within a list of “out of the way” or “lesser known” Key West establishments. But heaven help us, it’s just grand. Just around the corner from Mallory Square, where bizarre behavior and fabulous people-watching opportunities abound. Features the most stunning views of Key West Harbor and Gulf of Mexico sunsets you will find on the island (hence the name) with laughter, great frozen drinks and extraordinary live music creating an unmatched backdrop to the close of day. (Try the Pain in the Ass, which is simply a Piña Colada and Rum Runner, mixed). Yeah, the bartenders can be lazy and overworked (insist on the fact that you HAVE had a banana daiquiri here in the past, thank you) and the crush of the crowd can be a bit much. But push along regardless, find an unobstructed view, tilt your sweating plastic cup and b-r-e-a-t-h-e. On this most recent trip local musicians (including renowned guitarist Fritz Sigler) launched into a soulful rendition of “Guantanamera” just as the sun kissed the azure horizon, and bliss ensued. Get some of your own.

Hogfish Bar & Grill
6810 Front Street (Stock Island)
You’ll need a car, cab or scooter to get to this spot, as it’s located over the small bridge that separates Key West from Stock Island. You’ll also need a measure of faith to prove that it is indeed located at the end of a long maze of dilapidated buildings and trailer parks. But it’s worth the effort. The burgers they wrestle out to the tables are obscenely big, juicy and delicious, and the drinks are strong and cold. Their menu features a number of local treats, including Lobster BLTs, Baja Fish Tacos and their signature Killer Hogfish Sandwich. You’ll primarily find locals here, which adds to the color. Sit on a canal overlooking fishing craft or hide inside at the bar, then order some local fare and a cold one and blend right in. You’re on island time.

Virgilio’s Bar
524 Duval Street
On our trip to Key West last year we had a nice dinner at La Trattoria, a quaint Italian eatery that fronts Duval Street. Good food, sultry atmosphere. (If you follow suit, try to cop one of the two window seats to watch the passers-by). But on this year’s trip we stumbled onto a surprise. Back in the bowels of the building we found a dimly lit Virgilio’s Bar ensconced like an old-time speakeasy. Naturally, we dispensed with La Trattoria and ventured further in where two empty seats and a jolly bartender greeted us. We ordered food at the bar. It was good, not great. We ordered two dirty Martinis with blue cheese olives (given that it was Martini Monday), and they were great, not good. The place was quiet…for an hour or so. Then a local band featuring the aforementioned Fritz took a small stage, and the place bloomed with a vibrant crowd of (mostly) locals, all grooving to the sexy Latin beats. We stayed longer than planned, swaying to Fritz’s magic and blending in with the shop owners, waitresses, dancers, bartenders and other permanent residents. We’ll certainly be back, sans the sleeveless shirts and camera bag.
Find: a young Frank Sinatra
Bonus: name the five members of the Rat Pack

B.O.s Fishwagon
801 Caroline Street
Why would one assign an eatery an acronym most associate with body odor? And what the hell is a fishwagon? Questions that demand answers. We do know this: if Sanford & Son ever owned a bar, it’d be this one. Most patrons eat their meals with a sense of unease, waiting for giant metal jaws to pick up entire structure and drop it in a trash compressor. But they chew with gusto, especially the succulent conch fritters and chunky, skin-on fries. It’s a cash-only outfit, with friendly waitresses and enough trapped heat to cook a paella. Sit on the side nearest the bay, preferably under a chugging fan. Sweat out your silly worries.
Find: meat grinder
Extra credit: fishing reel

Hog’s Breath Saloon
400 Front Street, #C
Further up this list we lumped the Hog’s Breath into a group of overwrought Duval bars that are best seen not savored, but in truth it deserves better. Yes, the Hogs Breath-ers have sold out by adding a shop that sells everything from t-shirts to hot sauce. Yes, it reeks of shameful promotion, and its often populated by pseudo-bikers in pseudo-leather riding pseudo-Harleys. But Lord help us, it’s big fun. No bar on the island offers such a diverse and interesting variety of live music, beefier drinks or a more engaged crowd (not to mention occasional bikini contests that’d make Ron Jeremy blush). If it’s busy (as it often is) sneak around the back side of the bar, squeeze past the big tree, and set up camp next to the band. You’ll lose much of the hearing in your left ear, but after the third song or so you’ll be a bona fide Hog, hooting and swaying like a palm tree in a squall. (Leather chaps optional).

El Siboney
900 Catherine Street
If you’ve never eaten Cuban food, more’s the pity. And as Cuban cooks go, the folks at this out-of-the-way diner are wizards, whipping up mouth-watering meals, often from very simple ingredients. El Siboney (an alternate spelling of “Ciboney” a seafaring people who at one time occupied Florida and the Caribbean Islands) easily holds the Key West title for best “Cubano” food. Order up a pitcher of tart homemade Sangria, then try the ropa vieja (a Cuban beef stew that literally means “old clothes”), yellow rice, black beans and fried yucca, crunchy potato-like fries accompanied by a mysterious and tasty green sauce. And then, well, get sauced. An affordable, delectable eatery.

Blue Heaven
729 Thomas Street
You wake to a dull hammering noise, courtesy of your pounding temples. Damn those half-price Margaritas. The sun is already up and waiting like a wolf, and your stomach is making Chewbacca noises. What to do? Get thee to Blue Heaven, arguably the best recovery spot in Key Westdom. Secure a spicy Bloody Mary at the small bar while you wait for a seat – a hair-of-the-dog elixir that’s a great precursor to a celestial breakfast. Try the thick and fluffy banana pancakes, or opt for the more traditional Rooster Special – an apt name given the number of roosters and chickens strutting around the sun-dappled tables. Note, with a wry smile, that heaven is a sweltering spot.
Find: hanging skeleton
Extra credit: what’s the charge to watch someone shower?

THE WORTHY

Mangia Mangia
900 Southard Street
OK, we’ll admit it. We didn’t really eat at this off-the-path Italian restaurant – we went to meet a few friends for a quick hello, and interrupted their dinner in the process. And what a dinner. Their entrees had just arrived – a simmering selection of seafood, a stout salad loaded with colorful goodness, a wonderful-smelling red sauce over a billowing bowl of homemade pasta. As our friends ate, they made noises most would associate with bedroom pursuits. We talked. We drooled. We coveted. But alas, we had other plans, and we were off. We can’t, in good conscience, rank a spot where we didn’t actually dine in our top-shelf listing. But we’ll be back soon, harboring little doubt that Mangia Mangia will prove itself more than Worthy. Features indoor and outdoor dining…and thick atmosphere.

Willie T’s
525 Duval Street
We must’ve walked by this joint dozens of times in trip’s past, but we stopped this time to escape the heat for a moment. It was blind fate. Mojitos (a Cuban highball made from white rum, sugar cane juice, lime, carbonated water and mint) are a Key West staple, but Willie T’s has raised the bar, offering no less than 28 versions of the traditional libation. We chose the blueberry version, and it knocked our collective socks off. Delicioso. Bolstered by this kiss of luck, we decided to brave their ratty menu, ordering up Tuna Tataki and Mahi-Mahi wraps, respectively. Both were outstanding. The bartender had the personality of a cinder block, the place was dank and greasy, the dollar-bill-adorned walls are an overused ploy and the right-up-on-Duval profile made us leery, but you can’t fight the truth. And the truth is that the S.O.L. Lounge (love the acronym) delivered the goods, and then some.
Find: the “John Lusts/Loves Abby” $1 bill

White Tarpon Bar & Liquor Store
700 Front Street #107
Remember the girl you dated who always smelled good, smiled demurely and used proper grammar…but who left you sorta cold? That’s the clean and orderly White Tarpon. The drinks are top shelf (ask for a key lime martini complete with graham cracker dusting on the rim, or a thick and complex Key West Lemonade that belies it’s simple name). But the place has a crisp, somewhat pretentious feel likely due to the high-brow yachting set in the nearby marina. Better said, it lacks a measure of soul. An adjacent liquor store lends it a vaguely commercial feel, and the bright lighting would be perfect for an interrogation. That said, it’s worth the stop. We met a consummate gentleman named Al here who bought us a bottle of Argentinean wine while regaling us with stories of Viagra-bolstered Galapagos tortoises. We can’t make this stuff up.
Find: monkey wearing glasses
Extra credit: Fritz the Cat

Bottle Cap Lounge
1128 Simonton Street
A knowledgeable local told us that this place was once known for parking lot fights, loose women and shady dealings, but that it was now a respectable place to hang out. Nothing gold can stay. It charmed us, nonetheless. A traditional old bar is open part of the time, a newer lounge most of the time. The old bartender squinted at us knowingly through Coke-bottle glasses, and we liked him almost immediately. The Bottle Cap is a fair piece from Duval, which can be very nice, indeed. It’s a fun, if somewhat pedestrian, local dive.
Find: what might attack you here

Chart Room Cocktail Lounge
1 Duval Street
The Chart Room is a hidden sippery located within the sprawling (read: persnickity) Pier House Resort, which itself features several bars. Behind the non-descript entrance lies an abbreviated bar with a portion of charm. Not a large serving – more like a quick dab. But it’s worth a stop, since it’s the perfect spot for a breather away from the panic of Duval. Sidle up to the bar and order something cold, eye the nautical charts stapled haphazardly to the cork ceiling, and scoop up some hot popcorn or a handful of peanuts (noting the aged collection on the floor). No bathroom in sight, so plan ahead. But the air conditioning is crisp, the staff looks the other way if you decide to spark up a smoke, and there’s a certain port-in-a-storm appeal hiding in the creases. Very limited seating makes for a cozy feel that’s ideal for a couple or a small group. More than ten people in your party? The bartender may flee. An oversized old TV in the corner seems out of place and the setting within a resort seems to defy established criteria for a bona fide Key West bar, but somehow it all works. At least for a short time.
Find: a rubber chicken
Extra credit: hot dog (hint: it’s in a photo)

Schooner’s Wharf
202 William Street
How can you not dig a place where the musician’s dog cops a squat in a guitar case? This sprawling bar with multiple sections features tolerable live music, a good amount of treasured shade, and a nice elevated level with an epic view of the bay. The drinks were cold, but hardly haunting. It’s like a poor man’s Friday’s (the food chain, not the day of the week). A very poor man, with bad posture. Agreeable, but hardly inspiring. Check out the bookshelf in the back.
Find: Budweiser can bi-plane
Bonus: uptight pumpkin teddy bear

Pepe’s Steakhouse
Pepe’s is the oldest restaurant in Key West (est. 1909), so it deserves a measure of respect right off the bat. A cool dining room is available to stave off the cruel summer heat, and an open patio covered with dripping bouganvilliea provides shade and character. You can count the seats at the tiny bar on one hand, but Pepe’s serves good food indoors and out. The bartender was far from sparkling, but we give this spot good marks for vittles, strong drinks and local vibe. And we’re told they serve a mean breakfast.
Find: ice scraper/snowbrush
Extra credit: mousetrap

Banana Cafe
1215 Duval Street
This place moved to a new spot near the first location, but the great food, relaxing setting and hefty prices ($50 for 2 crepes, side of potatoes, 2 coffee, and 2 OJ) followed. Known for their crepes, the rest of the menu shines, as well. Hip, cool, comfortable, casual. And costly. If your palate is less than distinguished and your wallet is on the lighter side, Blue Heaven offers comparable fare for less…though you’ll miss the rush of blessed air conditioning.

Fogarty’s/Flying Monkey
We can’t give this place a fair review since we breezed in at around 11 PM for some late night sustenance and were back on Duval in under a half hour. But the Ahi tuna salad was surprisingly good, the drinks noteworthy and the wait staff on the ball. The huge patio right on Duval is a people watching mecca. A great late-night stop between drinkie-winkies.

Hurricane Joes
Like the Hogfish Bar, Hurricane Joe’s is also on Stock island, though it’s far easier to find. Good food and a waterfront setting that provides decent atmosphere are on the plus side, but the rental boats, fishing guides, kayak rentals and dive boat instructors bustling about the place tend to lend it a commercial feel that flies in the face of the relaxed setting that most longtime Key West lovers favor. Worth a look, especially if you’re activity minded. But not a long one.

Jack Flats
Can’t suggest sitting in a sports bar in Key West with so many more colorful options about, but Jack Flats has cold beer, pretty good eats and enough big screens to rank as the top sports bar on Duval Street, and likely on the entire island. Sneak in to see the big game, then sneak quickly back out. You can languish in a sports bar back home in Duluth.

THE WOEFUL

BigUns Sportsbar
If the name refers to the hulking cockroaches gliding under the barstools, it’s the perfect handle. They’re roughly the size of horseshoe crabs. Might (does) appeal to the young and drunken, but not seasoned vets. No velvet rope or body glitter in sight, but the “impromptu” bar-top dances, surly bartenders and pimply, record-spinning DJ nonetheless lend BigUns a “Beverly Hillbillies do South Beach” feel. Run.

Rick’s & Durty Harry’s
A cryer out front beckons with “Come visit our 13 bars.” Loosely translated, that means “We’re not sure what you like, so we’re throwing everything from a wine bar to a hard rock club to a VIP bar into a single over-wrought Barf-o-rama.” This Sybil of Key West bars has no concept of self. Durty Harry’s was passable, but the “band” on stage was poor. In fact, the lead singer forgot the lyrics to a requested song and we ended up carrying the chorus. If you’re a panting pubescent fond of launching Long Island Iced Teas against varied backdrops, welcome. If not, get thee to a proper drunkery.

The Conch Flier
Once a suitably dingy little haven with great view of the airplanes soaring in and out of Key West, the new version – in the new terminal – has the romantic appeal of a Brillo pad. With no views of the shimmering craft, what’s the point? Even a wonderfully winsome bartender couldn’t save the place, as two beers set us back $12…before the tip. (And they say pirates are historical figures). Yeah, it’s big, clean and close to the beach. So is my aunt Gertie in Lauderdale.

Jose’s Cantina
We heard this spot could rival El Siboney for great Cuban food. Game on. The sickly sweet Sangrias made us smile, but in the end the spartan interior and joyless staff lost the day. We scooted after a cassava appetizer, stopping to pinch the hostess – hard – on the way out. She didn’t even flinch.

Bourbon Street Pub
I can’t speak for you, but when I think Bourbon Street, I think beads, Mardi Gras, strong drinks and Cajun food. In Key West, the same term translates to lip-pursing, oil-slicked males in sequined t-backs, pulsing dance versions of Streisand’s Greatest Hits and come-hither looks from paunchy 50-year-old accountants. You’re gay. We get it. Without the man bag and short shorts we never would have known. Really.

Cowboy Bills
A country western style bar in Key West? Come on. I’m the son of a farmer, and I was raised on classic country music. But there ain’t nothing classic about plunky country rock, missing teeth and shameless inbreeding. If you enjoy bare-knuckle fights, spittoons, mechanical bulls and dolled-up bovines testing the structural integrity of plus-size jeans, you done found yer waterin’ hole. If not, skedaddle, pilgrim.

—–

Off to Key West now? Good for you. Go with a spirit of adventure, tempered with tolerance. And if you visit in mid-summer (the preferred time of year among many Floridians like myself), be prepared for mind-numbing heat – the type that, when mixed liberally with tasty libations, melts away inhibitions and philosophical differences and necessitates periodic, coma-like naps. Lose the cell phone, immerse yourself in the local culture and trudge swiftly from the welcome shade of one watering hole to the next in step with the other thirsty revelers. And know this: Key West always holds surprises. On this most recent trip, our innkeeper reported that he was chased by a shark while kayaking, a woman showed her prodigious chest to revelers so many times that even the most lascivious members of the crowd lost interest, and my wife and I drag-raced Hulk Hogan and his date on scooters at 1 a.m. Hulk won. No matter what craziness befalls you, by the time you have a few Margaritas and a new friend or two under your belt (hold the lewd remarks) you’ll be overcome by the seductive charm of the “Conch Republic”. Enjoy.