Article — Boston BarHopper

Shortly after my brother Andrew announced his engagement this past spring, I asked him a question that was sure to elicit a zinger. “Have you been thinking about what you want to do for your bachelor party?”

He didn’t disappoint.

“Yeah, since I was about 14.”

If you know my brother at all, you realize he wasn’t exaggerating.

So what was the outcome of his approximately 19 years’ worth of planning? A weekend of drunken debauchery in one of the most popular destinations in the world – Key West.

Known for its tolerant, easygoing island culture, Key West has been called home by the likes of Ernest Hemingway, whose spirit still looms large over the island, and Jimmy Buffett, who made a career and a fortune by singing about its boozy, laid-back lifestyle. A favored destination of presidents and celebrities of all stripes, the southernmost city in the United States has a lot going for it – fun tourist attractions, a long and colorful history, unique architecture, breathtaking sunsets.

At least, that’s what I hear.

My brother didn’t choose Key West for its sightseeing opportunities (actually...eh, never mind). No, this was a drinking trip, and the city’s (in)famous Duval Street boasts one of the more impressive concentration of bars in the country. The bars open early and close late, and there’s a lax open container law – meaning you can roam the streets with a drink in your hand. In Andrew’s words, “it’s like Bourbon Street in New Orleans, but clean.”

So a bunch of us piled into a van and made the four-hour trek from my brother’s place in Pompano Beach to Key West. There won’t be a quiz or anything, but just for archival purposes, the crew ultimately consisted of the following characters: Andrew and myself; our friend Paul, who was celebrating his own bachelor party; my cousins Adam and John; and Mickey, Kenny, Mike, Gary, Steve, Ryan, Kevin, Powell, and “Mayday” Malone.

What followed were two days and nights packed with all the shenanigans, nonsense, and sophomoric humor you’d expect of a proper bachelor party. We made no friends and possibly a few enemies. There were exhilarating highs and embarrassing lows (the nadir coming when one member of our group emptied a bar of its customers with his flatulence, drawing a stern reprimand from the bartender). There were also plenty of bars, needless to say, and since there’s no point in mentioning every one we hit, I thought I’d pick a couple to focus on. The two we’ll look at are complete opposites, in many respects; but both are steeped in local history, and each offers a different perspective on drinking in this splendid, quirky city.

Opinions may differ on which Key West bars are considered “must visit,” but given the illustrious clientele that Captain Tony’s Saloon has entertained over the years, you’d be hard pressed to pass this one up. More importantly, this is a bar that truly epitomizes the character of Key West – a kaleidoscopic mix of history, legend, charm, and delightful eccentricity.

Captain Tony’s is named for its longtime owner, the late Tony Tarracino. Even in a city known for its colorful characters, Tony was truly larger than life. Born in New Jersey, Tony dropped out of high school and made money as a bootlegger during Prohibition. He later graduated to gambling, but when one of his schemes burned the Mafia, the mob took him to a New Jersey dump, beat him within inches of his life, and left him for dead. He survived, though, and fled to Key West in 1948.

You might say life improved a bit for Tony upon his relocation. After a series of odd jobs such as a charter boat captain, a shrimper, and a gunrunner smuggling weapons and mercenaries to Cuba, Tony purchased the bar that still bears his name. He owned it until 1989 – when he was elected mayor. Universally lauded as one of the most popular citizens of Key West, Tony died in 2008 at the age of 92. But his legacy lives on at his namesake bar.

It seems only fitting that the history of this bar is as long and peculiar as that of its legendary owner. The building itself dates back to 1851, when it served as a morgue. In subsequent decades it became the site of a telegraph station, a cigar factory, a brothel, and during Prohibition, a series of speakeasies. It began legally serving drinks in 1933 as Sloppy Joe’s, which later moved down the street and still operates today.

Varied and unusual as the building’s past may be, the present-day incarnation is infinitely more bizarre.

Captain Tony’s is without doubt one of the strangest bars I’ve ever set foot in. The walls and ceiling are almost completely plastered with business cards, dollar bills signed by patrons, license plates from all over the country, and a collection of bras that would rival the inventory of Victoria’s Secret.

And that’s just the beginning.

You can’t help but notice the 200-year-old tree growing from beneath the floor and through the ceiling. This is known as the hanging tree – because it was used for hanging people in the 19th century. Apparently 17 people got the noose here: 16 pirates, and one local woman who murdered her family…and is rumored to haunt the bar to this day.

Indeed, there are plenty of creepy accounts of paranormal activity in the bar. And while there may or may not be a ghost in Captain Tony’s, there most certainly is a corpse.

I thought this “grave” was just for effect, but no – the remains of an actual person are under there.

The fire hydrant almost seems passé by comparison.

The rest of the décor is less grim but no less fascinating. A gallery of framed photos, news clippings, and paintings of the Captain adorn whatever wall space isn’t already occupied by dollar bills and undergarments.

There’s a good-size pool room. Right off of the pool room (you’ll need to step over the grave) is another room with a foosball table and an old Ms. Pacman arcade game.

There’s a stage in the back, which is where Jimmy Buffett got his start as a performer (he immortalized the bar and Tony in his song “Last Mango in Paris”).

And speaking of famous, check out the barstools. Each is painted with the name of a celebrity who’s visited the bar. Actors, musicians, authors, politicians, presidents, athletes; you’re drinking in pretty good company here. (I assume the owners got started on the Boston BarHopper stool shortly after I left.)

In addition to serving as a monument to its former owner, a depository of random mementos, a de facto museum of local artifacts, and a resting place for the dead and undead, Captain Tony’s also serves drinks. The beer selection is pretty standard, but the drink of choice here is the Pirate’s Punch. The recipe is a secret but, like most Key West drinks, contains plenty of rum. You get a generous portion in a commemorative cup for $7.99.

For all the things that make Captain Tony’s unusual, it is in many respects typical of the bars in the vicinity – dark, divey, and well worn. You can enjoy a mellow afternoon with some light beer, listening to the singer/guitarist as he customizes songs for the sparsely populated crowd.

By nightfall the crowd will have swelled, you’ll have downed some frozen drinks and maybe a couple of shots, and you’ll be screaming along while the cover band plays “Don’t Stop Believin’” or some other crowd-pleasing staple.

This is not, by any stretch, a bad thing.

At the same time, you can be forgiven for wanting a change of pace. While plenty of the bars on and near Duval Street cater to revelers in search of a quick and easy buzz, there are options for the more discerning cocktail crowd. And for that we head a mile or so down the road.

What is now known as the Speakeasy Inn was once the home of Raul Vasquez, another favorite son of Key West. Vasquez worked in the cigar industry until 1920, which is when Prohibition went into effect. Recognizing the entrepreneurial opportunities associated with the 18th Amendment, Vasquez set up a speakeasy behind his house and became a rumrunner, making frequent trips to Cuba to stock his illicit bar.

Of course, one of the challenges of running a hidden bar is that it’s difficult for customers to find; and you can’t exactly put up a big sign advertising your illegal products and services. Vasquez found a clever way around that problem. On one of his trips to Cuba, he purchased some elaborately carved balustrades for his house.

Tasteful and decorative, yes they are; but a closer inspection reveals liquor bottles, hearts, diamonds, clubs, and spades carved into the woodwork. These shapes served as a subtle hint to those in the know that liquor and card games could be found in the club behind the main property.

The balustrades still exist, as you can see, and the Speakeasy Inn is now a Key West landmark. It is one of the only buildings in Key West with a basement – which, of course, was used for hiding liquor. But the booze doesn’t need to be hidden anymore, and neither does the bar, which has moved to the front of the building and is now known as the Rum Bar.

This refurbished building truly feels like an old but well-maintained home. Small and cozy, its creaky hardwood flooring, wooden walls, and crown molding make for a comfortable, intimate atmosphere (though I suppose the bras in Captain Tony’s evoked a sort of intimacy in their own right). There’s an L-shaped bar with about 11 seats, and a few tables in the corners. Windows on all sides of the room let in ample sunlight, further contrasting the Rum Bar with some of the darker dives we’d been inhabiting up until that point.

It was fairly early on Saturday (“early” being a relative term at this point) when I stopped in with Andrew and Paul. The Rum Bar is, unsurprisingly, known for its expansive selection of rums, which find their way into some of the best drinks on the island thanks to the cocktail sage behind the bar – “Bahama” Bob Leonard.

I’d first heard about Bob from my brother, who makes the occasional trip to Key West even when he’s not having a bachelor party (ah, the benefits of living in South Florida). Andrew would often tell me about the great drinks he was having at the Rum Bar, urged me to follow Bob’s blog, and even sent me an autographed copy of Bob’s book of cocktail recipes and island tales (autographed by Bob, not by Andrew).

So here I was, at long last, face to face with the man, the myth, the mixologist, Bahama Bob…and I suddenly realized I needed to order something. So of course I was like….”ohhh, uhhhh, I don’t know…rum and Coke maybe?” Thankfully Paul stepped in and recommended I try one of Bob’s many specialties – the Papa Dobles. Also known as the Hemingway Daiquiri, the Papa Dobles is made to the late author’s specifications – no sugar and double the rum (hence the name, which roughly translates to “Papa’s double”). Hemingway liked his drinks strong and not too sweet, and this mix of white rum, grapefruit juice, lime juice, and Luxardo maraschino liqueur was almost like a dry daiquiri. The grapefruit added a pleasant sour essence.

With that we settled in for a round of classic island drinks. Now let’s face it – there are few scenarios in which you can order a Pina Colada at a bachelor party without enduring some heavy taunts from the rest of the group; fortunately, drinking at a rum bar in Key West is one of them. Paul took advantage of the setting and began with an exceptional Pina Colada.

Andrew went with another regional favorite in the Rum Runner. A mix of light rum, dark rum, banana, blackberry, and fruit juices, it was strong and bursting with flavor.

Next up for me was the Pain Killer – Pusser’s rum, cream of coconut, orange juice, and pineapple juice. Pusser’s rum differs from most other rums in that it’s distilled in a wooden pot still instead of a metal one, with no flavoring agents or sugars added after distillation. Rich and dark, it made for a strong, naturally sweet cocktail with a distinct rum flavor that didn’t get buried beneath the juices.

As much as we were enjoying our drinks, it was Andrew’s next choice that demonstrated what a unique place the Rum Bar can be to drink. The “Bark” and Stormy is a variation of the well-known Dark and Stormy, swapping out dark rum with something called “Bahama Bob’s Bark Juice.”

Intrigued, I had a sip of Andrew’s drink. Yes, it was reminiscent of a Dark and Stormy, but the mysterious bark juice gave it a smoother, more vibrant freshness.

The bark juice is Bob’s own innovation, and as the name suggests, it involves tree bark. In short, Bob takes different types of bark from all around the Caribbean – Key West (of course), Barbados, Antigua, St. Lucia, the Virgin Islands, and more – and infuses them with white wine and honey. After a couple of weeks he strains the mixture and adds 151-proof rum, letting the barks soak for a few more weeks.

The resulting elixir is positively exquisite. I quaffed down a generous shot, expecting the familiar burn that accompanies any straight alcohol. But this was smooth as silk – not bite whatsoever. The earthy, woodsy, herby freshness made me wish I had sipped it slowly to savor the spirit as well as the moment.

In addition to being a highly skilled mixologist, Bob is quite the genial character. As he whipped up complex cocktails for an ever-expanding crowd, he regaled us with stories about his drinks, his travels, and the island he calls home, never missing a beat or anybody’s order.

Eventually the rest of our group started trickling in, and we began discussing our next move. I opted for one more round, knowing that my chances of finding cocktails this good anywhere else on our journey were pretty slim. My final choice was the Goombay Smash – a potent mix of light rum, coconut rum, peach schnapps, orange juice, and pineapple juice.

Strong and fruity, with a prominent peach flavor, it was a satisfying conclusion to my long-awaited visit to the Rum Bar and set the tone for the rest of the day.

Which included a rum-induced nap.

Last Call

No, I didn’t make it to the Ernest Hemingway Home and Museum. Nor did I witness one of the island’s majestic sunset celebrations in Mallory Square. I didn’t smoke a cigar, eat Cuban food, or get a picture of myself at the concrete buoy marking the southernmost point in the continental United States. Not that I feel like I missed out; I just have a lot of reasons to go back.

Besides – who among a group of 14 dudes in various states of inebriation and rowdiness is going to say “Hey guys, let’s go watch the sunset!”

Local attractions or no, I definitely soaked up the Key West drinking experience. I’m sorry I don’t have a full report on bars like the Lazy Gecko (known as the nation’s southernmost Red Sox bar), Irish Kevin’s, the Green Parrot, or anywhere else we stumbled into. They all have their own style and character, but the scene is similar to what I described at Captain Tony’s – a laid-back vibe, live music, cheap drinks and lots of happy people throwing them back.

At the risk of unfairly painting all those bars with one brush stroke, I’d say they’re more about quantity than quality when it comes to drinks. Almost everywhere you look, you’ll see happy hour specials, cheap beer in plastic cups, and very basic, island-themed mixed drinks. There’s nothing wrong with a $6 cup of some brightly colored, cloyingly sweet concoction, but they can be hit or miss.

I'm pretty sure this "Mai Tai" was mostly grenadine with a splash of rum. Still, I drank it.

Fortunately, quality drinks are available if you know where to look. The Rum Bar certainly isn’t the only place where you can get expertly crafted cocktails, but with “bark juice” and a slew of house-made syrups, you’re getting original creations that you won’t find anywhere else on the island.

So whether it’s a quiet afternoon of craft cocktails with Bahama Bob or a booze-fueled Duval Street bar crawl – or both – there’s more than one way to enjoy yourself in Key West.

Finally, I’d like to congratulate my brother, who gets married next month, and Paul, who gets hitched in February.

They orchestrated an incredible weekend for 14 people, and in the haze of it all, it was sometimes easy to forget that they were the guests of honor.

Then again, on a weekend like this, it was easy to forget a lot of things.

Captain Tony’s Saloon: 428 Greene Street, Key West, Florida

Website: http://www.capttonyssaloon.com/

The Rum Bar at the Speakeasy Inn: 1117 Duval Street, Key West, Florida

Website: http://www.speakeasyinn.com/

Bahama Bob’s Rumstyles:http://bahamabobsrumstyles.blogspot.com/

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One for the Road – Adventures in Key West

Matthew Maslin