I’m sitting on a barstool staring down a pint glass full of frozen margarita. I haven’t had a frozen margarita in years, it makes me feel a little twenty-one again. A woman with big round sunglasses pulls up a stool alongside Barrett, who’s sitting next to me. She eyes my drink longingly, asks how it is. She, too, hasn’t had a frozen margarita in years. The heat in the open-air bar is thick and buttered popcorn smell hangs in it unapologetically. There’s a vintage bicycle dangling from the ceiling above us, along with a half a dozen license plates, stickers, and an old parachute, the kind that’s wide as a room and that was maybe once used in an elementary school gym class for games. It reminds me of the best parts of childhood. I sip my drink, Barrett sips my drink then asks for a second straw, we both nod to the sunglassed lady approvingly. No frozen drink has ever tasted this good in all the history of drinks.
Truth be told, our expectations weren’t high for Key West. “You know…it’s just Key West-y.” That was the typical response we got when we asked fellow Keys-ers about the southernmost city in the continental U.S. Usually, their response was followed with a half shoulder shrug or an eye roll or maybe both. What’s it like? Is it worth the two-hour bus ride from where we were docked in Marathon? Their responses painted a bleak portrait of the small island as an uber-touristy, commercially-driven unrefined grown up kind of spring-break destination. A place where adults fumble down dusty streets with the stink of day-slosh worn on sweat-stained clothes.
This stereotype, though, was the exact opposite of our experience.
Well, maybe not the polar opposite. There were, admittedly, about a dozen adults bicycling through town in varying shades of neon-colored tutus as participants in a hilarious and unabashedly boozy scavenger hunt. But there was also a certain tropical charm and a kind of bohemian artistry. Wide wooden wrap-around porches with fans that swept humid air downward in cascading loops. Palm tree-shaded yards and art galleries built out of 200-year-old stone churches that housed island eccentricities, woodwork and paintings, art that spoke words of the sea and her surroundings. Urban chickens puttered down side streets and live music spilled from local watering holes where the not-quite-sloshed (or at least let’s call them elegantly-sloshed if there is such a thing) day drinkers sipped on Hemingway daiquiris while bartenders squeezed their way through endless crates of limes. The loud crack of pool balls and an acoustic guitar filled the space in between.
We only spent a day in Key West before continuing our not-so-patient wait for a good weather window to sail from Marathon to the Bahamas. And it felt like we only scratched the surface of this zany, islandy, creative person’s paradise that has over the years attracted artists big and small, kitschy and clever, from Jimmy Buffet to Ernest Hemingway.
Of course, I am no expert on the town, having spent only a single day there. But I feel confident in putting this humble guide out there as, perhaps not the definitive or exhaustive guide, but rather a really loose guide for how to have some fun moments should you be lucky enough to find yourself in Key West.
Lunch at Garbo’s Grill
If you’ve arrived around lunchtime, there will likely be dozens of restaurants that call to you, many with open aired spaces overlooking the buzzy Duval Street. We spent lunch, though, posted on a shady patio next to the much talked about airstream that houses Garbo’s Grill. While the menu might be limited in items (I think I counted a total of six), it’s anything but limited in flavor. Each dish punches a tantalizing balance of sweet, salty, sour, umami, and spicy.
Tip: We liked each bite we had there but the Bulgogi Korean BBQ Burrito was a unanimous favorite.
Old Stone Church Art
We hadn’t planned on stopping in Rockhouse Masterpieces, a church-turned-art-gallery that sits on a quiet side street, until we spotted a small iguana happily resting in a Buddha statue’s lap at its entrance. It was a sign, we thought. We should definitely stroll through the sweet stonewalled, heavily air-conditioned gallery. We were wowed by the art and furniture space from the moment we walked in. Entire wall-sized photographs of sea creatures that seemed to jump from their frames. Pastel wood carvings with brass detailing and island-inspired paintings.
Tip: This is only one of the art galleries in Key West, but there are many around town. See this list for a few more places to get your art-interests piqued.
Almost the Southernmost Point Buoy
Okay, so it’s technically not the southernmost point in the continental U.S. but it’s pretty darn close. This Black, yellow, and red buoy was one of the more populated (read: crowded) things we did on Key West and would probably be lower on my list of recommendations if you’re crunched for time. But, that said, it was also kind of surreal to see the “90 miles to Cuba” painted across it in bold italics, knowing we’d just made a 192-mile crossing across the northern end of the Gulf of Mexico. A hundred-mile sail to Cuba suddenly felt all the more attainable.
Tip: Can’t make it to Key West in person? Check out what’s going on at the Southernmost point with this live webcam.
At Home, at Hemingway’s
We wandered the streets more after the southernmost point, going nowhere in particular except where we felt inclined to let our feet carry us. A quick turn here, a quick selfie with a chicken there, and next thing we knew we were outside of the Hemingway Home, a sprawling palm-studded cat paradise. Towards the end of the hour or two we spent roaming the house, I found myself somehow alone, without another visitor in sight, at the edge of Hemingway’s airy writing studio. I closed my eyes for a few seconds and hoped that some of the magic he had with plot and dialogue would rub off on me. I’m not actually holding my breath for this to happen but one house cat did, curiously, rub against my shins at that exact moment, so who knows, maybe it’s a sign.
Tip: Have you read much Hemingway? What are your favorites? I just finished Old Man in the Sea and all I can think about is how badly I want to land a marlin.
Frozen Margaritas at Green Parrot
Remember the scene described in the intro at the very beginning of this post? It takes place in Green Parrot Bar, which is conveniently located just two blocks from Hemingway’s. We stopped in for a single drink and ended up staying for a few. And, it turns out, we got some really great recommendations from knowledgeable locals for our next two stops.
Tip: Though we didn’t stay here into the night, there is a live music schedule that was highly talked about in town.
The Real Sloppy Joe’s?
Maybe you’ve heard about how Hemingway once slung lime-laced cocktails in a place called Sloppy Joe’s, maybe you haven’t. Either way, one thing to know is that there are two places that lay claim to Hemingway’s drinking day inspiration, one called Sloppy Joe’s and one called Captain Tony’s. I won’t go into the debate (or lawsuit) hatched between these two places, you can read more about it here. But I will say that we wondered into both and chose to only stay for a drink at one: Captain Tony’s. Whether Hemingway truly drank and found inspiration in those walls and amidst the real tree that grows through its main quarters, wasn’t important. Whether we could have a decent drink (although with a somewhat limited beer list), listen to live music, and play a leisurely game of pool, which I definitely did not win, all in a space that’s covered, in some places an inch deep, in dollar bills and other assorted items from the years. Somehow it just felt much more Key West than Sloppy Joe’s.
Tip: Although we didn’t choose to stay at Sloppy Joe’s, there were some interesting Papa artifacts hanging around its parts that might make it worth a stay to some.
If Only, Onlywood
If there is one thing we wanted after a busy afternoon and miles spent on foot, it was a comfortable chair and piles of food. “You must, must, must go to Onlywood,” the sunglasses-wearing-frozen-margherita-eyeing patron at Green Parrot told us. Having no real plan, no real sense of the food scene in Key West, we agreed we would and soon found ourselves on an open-air patio, tucked in quietly off the busy streets of the city, with a bottle of reasonably priced dolcetto between us and a wood burning fireplace in the background. A plate of truffle-scented arugula salad, a bowl of house-made gnocchi with pesto and fresh caught Gulf shrimp, and one wood-fired pizza later, we were so full we could hardly walk to the bus station for the last bus out of Key West. We made it there, thankful to the nice sunglassed lady at Green Parrot for the tip on the best restaurant we’d dined at since we left New Orleans two months ago, and hopped on a bus to head home.
Know of any great spots in Key West? Any must do’s? We’re likely headed back through the Keys on our return sail back into the States sometime next year and I’d love to hear your suggestions in the comments!