When I was a kid in SoCo (that’s Southern Connecticut to you and me, Russ), we lived not too far from this little amusement park in Rye Beach, NY known as Playland.
By today’s mega-park standards, it wasn’t much–kinda like Mini Me to Cedar Point’s Brad Pitt. But when the magic words “Wanna go to Playland?” were heard in our house, it was like Christmas, my birthday, and the last day of school all rolled into one, and I’d go completely outta my mind in anticipation.
Flash forward to adulthood. I get the same rush every time we head down to a tiny chunk of palm-treed rock at the bottom of the contiguous US that’s been a stomping ground for centuries for everyone from pirates to Monopoly Men industrial icons to US presidents.
If you’ve never been, you should understand right up front that KW is not for everyone. Here’s a quick quiz to see if it’s what you’re looking for:
Are you wound tighter than a Baptist baseball and have no desire to un-tighten?
Is your regular bedtime no later than 10pm?
Is Jeff Foxworthy your idea of a wild, cutting-edge entertainer?
If you answered YES to one or more of these questions, then…um…yeah, there are other vacation destinations in the Sunshine State that would almost certainly suit you better (lovely Amelia Island comes readily to mind).
But for those looking for something a little different, left-of-center, off the proverbial path, where the unexpected is an everyday norm, your Playland awaits.
So, what are we waiting for? Let’s roll…
HOW WE LIKE TO GET THERE
Not a plethora of direct flights into Key West Airport, but even with a connection along the way it’s worth it. The lower Keys already feel 3rd World anyway, and this tiny airport definitely fits the bill. You walk off the plane onto the hot, sticky tarmac itself, and the message on the side of the terminal reads “Welcome to the Conch Republic”, a nod to their tongue-in-cheek cessation back in 1982.
The whole place is about the size of a Delaware K Mart.
Expect to pay about $25 for the 15 minute cab ride to the downtown/Duval St area. Expensive, but better than renting a car, as parking can really suck in the downtown area.
If you have a little more time, consider flying into Miami or Ft Lauderdale, renting something cool, and following the Florida Turnpike down to Overseas Highway, one of the all-time great scenic drives. On the downside, it’s mostly one lane in each direction, and dang easy to get trapped behind a long line of Winnebagos and trailered fishing boats. But the infinite blue panoramic view, especially from Seven Mile Bridge, is magically delicious.
WHERE WE LIKE TO STAY
There’s several fine hotels all over the island, but we honestly prefer Key West’s stellar B&Bs. Normally, I’m SO not a B&B guy, as I don’t understand the point of doilies, but KW-style can be a universe away from the B&B norm.
Our favorite is the Mermaid & the Alligator (729 Truman Avenue). It’s not exactly cheap (around $300 a night in season), but the place is a classic Key West Victorian, circa 1904, with dark, oiled wood, high ceilings, wrap around balconies, warm breeze flow-thru, each room an autonomous theme (with private bath–bonus!). We chose the Audubon Room, with louvered patio doors that open out to the grotto, complete with exotic plants, plunge pool. and the sexy, original statue that inspired the inn’s name. The sun-dried tomato frittata and fresh-baked muffins we had for breakfast were delicious day-starters, for sure. And 4pm is afternoon wine time, complimentary for guests.
Mermaid & the Alligator is close enough to the action that you can walk to the bars and restaurants, yet you’re far enough away that the Last Call diehards aren’t peeing outside your window and singing slurred Buffett tunes at 4am.
One tiny little disclosure: M&A sits across the street from a Catholic church that kicks in the bell chimes about 7:30 am daily, so be aware if you’re a light (or late) sleeper.
Mrs. Bunny says: We prefer to be away from the bars for where we stay, sexy and fun are just a bunny skip away!
HOW WE LIKE TO GET AROUND
Like I said, car parking can be an expensive and time-sucking pain in the coconuts on and around Duval St. So instead, we rent scooters, which you can park just about anywhere, for free (just remember where you’ve parked, as they’re everywhere down there, and they all look the same! We’ve seen several hungover scooter-hunters wandering the streets the morning after).
Some rental companies will deliver them right to your door, and pick them up again when you’re done, at no extra charge. And they like to haggle too. I ended up getting 2 scooters for 3 days for $50 total, delivered, after a little wrangling. Talk to the front desk or concierge for a recommendation.
Scooters are super-easy to ride. Even Mrs. Bunny went from “yikes!” to “yahoo!” in about an hour. They’re automatic (so no gear shifting), they’re key start, and they have lockable storage under the seat. Top speed is roughly 40mph, but it takes about four days to hit it.
Mrs. Bunny says: Holy crap! I have never ridden a motorized bike, and omg it was scary at first. But after running around on some quiet side streets, I quickly got the hang of it. Mrs. Bunny advises to not drink and scooter. If going out for the evening, please walk. It’s a softer landing.
Other free-parking vehicle options: bicycles, electric golf cart-looking things.
Key West is a foodie playground, and as always, we go local and avoid the chains. As you can probably guess, there’s plenty of fresh local fish like grouper, tuna, mahi mahi, ballyhoo, conch, shrimp, stone crabs (beware MD Steamed Blue Crab lovers: Stones are boiled and served chilled, no spice, w/mustard sauce for dipping. They’ve got a strange aftertaste that neither of us cared for), plus great steaks, French, Cuban, Spanish, Italian, even good bar food. Here’s a sampling of our favorites:
1. B.O.’s Fish Wagon (801 Caroline St)
Not gonna lie to ya; B.O’s is more of an open air shack than a restaurant, but that’s part of the charm. Fresh grouper and mahi mahi sandwiches (grilled or fried), fresh-cut fries, cold beers, and live blues and jazz music make the Shack a fantastic option for lunch or between pub snack. Figger about $10-$15 to fill your tank.
Mrs. Bunny says: Great place for a hangover, ’nuff said!
2. El Sibonay (900 Catherine Ave)
El Sibonay is on over on the quiet side of the island, and is, hands-down, the best Cuban food we’ve ever experienced. Even my Havana-born father was raving about their marinated pork, fried plantains, and cafe con leche.
This place ain’t first-date fancy. It’s lit up like a cafeteria, you’ll almost certainly have to wait (outside) for a table, and they don’t even bother taking your name (you get a number when you get there). But not only is it fantastic food, the prices are unbelievable (that’s GOOD unbelievable!).
Mrs. Bunny says: Dinner was two orders of marinated pork with sides, black bean soup, a pitcher of homemade sangria, and two flans for dessert = $42 WITH TIP! Furthermore, we could have shared an entree as the portions were HUGE! Still have cravings for their food. Awesome.
A&B Lobster House (700 Front St)
Touristy, yet amazing, A&B is a Key West institution. This is a world class lobster house, with an expansive view of the harbor. The top floor is fancy-schmancy gourmet, and expensive (about $75 a head for dinner + drinks), with both fresh Maine and local spiny lobster on the menu.
Downstairs, Alonzo’s is more lax, and offered a Happy Hour (even on Saturday) that featured cheap drinks and 2-for-1 seafood apps.
(“Only in Key West” side note: while deciding what we wanted to eat at Alonzo’s after several hours of Duval Crawling, I felt something poking me in the back. I turned, and this fairly hammered little woman at the next table says “ya gotta try thish here smoked bluefishhhh. F*cking amazing!” and then proceeds to slide the plate onto our table. So we dug in. The smoked fish was damn good, and her much-saner boyfriend was a cab owner who ended up taking us back to the airport a few days later for only $12.)
AVOID: Mangia Mangia (900 Southard St)
The only thing worse than their mediocre pasta dishes is their painstaking attention to rude and disinterested service. Picture Olive Garden with far less flavor and staffed by NYC bus drivers.
Mrs. Bunny says: While I will admit to being a bit ‘under the weather’ for this dining experience, I did wake up the next day remembering a certain level of rudeness permeating my buzz!! No fun!
DRINKS & NIGHTLIFE
Now we’re getting to the heartbeat of Key West. They make alcohol an art form down there, with diversity, creativity, and open-arms attitude. Sure, you don’t HAVE to drink while you’re there, but that’d be like going to church and avoiding all the religion parts.
They’re pretty lax about drinking down there, provided that you’re not acting like a raging asshole. For example, there’s this little bar on the Duval St sidewalk that’s basically like a newsstand. No idea what it’s called, but you can’t miss it. You can grab a beer or cocktail there, and just head on down the street with it, no worries. And if you’re in one bar, and suddenly decide to roll to the next place, you just do it, drink in hand. Just be sure to ask for a to-go cup.
And look: KW has more bars than Alaska has ice cubes. It’s impossible to hit them all, unless you live there, and you’re independently wealthy and constantly thirsty. We’ve only scratched the surface ourselves.
Irish Kevin’s (211 Duval St)
I know it says “nightlife” at the top of this section, but Irish Kevin’s also offers…uh…MORNINGlife, as beers and live acoustic music can start as early as 10am every day of the week during season. Kevin’s is 100% touristy, but that’s cool because it’s a total trip. You may be coaxed by the onstage performer to kiss your significant other when you walk in (cheers will ensue), you may be part of the “running of bulls” where a group of bearded patrons with viking helmets chases a female customer down the street, and you might be heckled when you leave for not sticking around.
Mrs. Bunny says: As my friends/family will confirm. Irish Kevin’s is always the first place I lose the ability to spell while texting about the great time I’m having.
Sloppy Joe’s (201 Duval St)
Basically right next door to Irish Kevin’s, Sloppy’s may be the best-known watering hole on the planet, made famous by Papa Ernest Hemingway (albeit at their original location, about a block and a half away). Sloppy’s sits on a corner, with open entry all the way around that brings in the breeze, street sounds, and thirsties. Like Kevin’s, it’s always a party.
You gotta do Sloppy’s at least once. Grab a drink, call your friends, and make them jealous as hell as you wave to them at the webcam out on their Duval side. And if you get lucky, maybe you’ll catch the great Pat Dailey performing on Sloppy’s stage. Pat is another KW institution, in his mid-60s, and still a wildman.
Bull & Whistle (224 Duval St)
Yeah, the Bull is a solid go-to, with live rock bands day and night in season, and there’s decent pool tables up on their second floor. But what REALLY makes this place like no other is what’s on their THIRD floor rooftop.
It’s the Garden Of Eden, clothing optional bar.
You just don’t see these kinds of things in places like Davenport, Iowa, do ya. Like Sloppy’s, it’s worth checking out at least once. Yes, you will probably see naked people (unless it’s c-c-c-COLD out!), no, you don’t have to disrobe if you don’t want to. No, it’s not an orgy (but we HAVE witnessed some interesting dance floor escapades!). Yes, it’s one hell of a good time.
Mrs. Bunny says: Ladies, it’s not as bad as you think. Sure, there’s the occasional fat, bald, naked guy in view. But for the most part it’s very laid-back and relaxed, with less rampant testosterone than you might think.
1. La Te Da (1125 Duval St)
Cool little outdoor bar with live jazz music + cabaret that has both hetero and homosexual clientele. Great option if you want something a bit more upscale and less turbocharged than down on the louder end of Duval. Last time we were there, this cool couple we met from Pittsburgh was having so much fun on the dance floor, they fell down the stairs and right out the front door, with a potted plant landing on top of them for a great cartoon ending! No injuries, so it was funny.
2. Schooner’s Wharf (202 William St)
Whenever I hear the term “Salty Dog”, I immediately think of Schooner’s. Old-school Key West joint, over on the waterfront. Apparently this was Jimmy Buffett’s hangout back in the early 70s, when he was just another unknown singer/songwriter.
OTHER COOL THINGS
So, besides drinking, eating, and looking at naked people, KW does have some other options for your attention.
1. Ernest Hemingway House (907 Whitehead St)
Sure, as I writer I geeked out when I got to check out Papa’s Key West home, but it’s a good time for most adults (kids would likely be bored, but why are you bringing kids to Key West in the first place?). The house is magnificent, with tons of photos and memorabilia, a swimming pool that cost several times more than the average annual household income when it was built, the latest generation of Hemingway’s family of six-toed cats running around, and his writing loft in the outbuilding, complete with the original typewriter.
2. Mallory Square (1 Whitehead St)
Come for the world-class sunsets, stay for the world-class street performers. The Square gets packed as the day goes on, so arrive early for a prime spot along the rail, grab a snack, and wait for Mother Nature to break out the paint brush.
3. Butterfly Conservatory (1316 Duval St)
Exactly what you think it is, you’re surrounded by hundreds of technicolor moths as you tour the conservatory. Guys, yeah, I know, it sounds about as exciting as shopping for curtains, but it honestly was pretty cool.
4. Fort Zachary Taylor State Park (601 Howard England Way)
Key West’s most popular beach, but that’s not saying much. The sand part is just fine, lush and tropical, with the famous “mileage” sign, and a decent snack bar. But like most beaches in the keys, there’s a ton of rock and coral under the water’s surface. Wear water shoes, flip flops, something. Or just chill under the palm trees, because the view is unparalleled.
4. Southernmost Marker (201 Front St)
Another iconic photo op, this buoy typically has a line of folks waiting to snap a pic. Took us about 10 minutes, chatting with a Dutch couple behind us, who ended up serving as our photographer.
5. Key West Cemetery (701 Passover Lane)
Like everything else down there, this cemetery isn’t your normal breed. Dating back to the 1840s, the graveyard has sections for Cuban Freedom Fighters from the Spanish American War, Confederate Navymen, and the Battleship Maine, plus some individual stones with memorable epitaphs (one woman’s reads “See? I told you I was sick.”)
BE AWARE OF…
Here’s some other info that might come in handy.
1. Chickens roam free
These wandering KFC menu items date all the way back to the 19th century, when Key West was a fairly lawless fishing and sailing village. Cockfighting was a popular sport back then, mainly because ice dancing hadn’t been invented yet. When civic leaders tried to bring a little order to the island, they outlawed the feather-based brawls, so their owners either ate their warriors, or set them free. Waking up to ‘cock-a-doodle-doo’ is completely normal down there.
2. Beach swimming isn’t great–Like I said, there’s rocks and coral aplenty as soon as you step into the sea, all through the Keys. If you’re jonesing for a true swim, your best bet is to head north up to Bahia Honda State Park, about 20 minutes north of Key West. Try their north side (to the left) as you enter. This is the best stretch of beach we’ve found, south of Miami. And, if you see something that looks kinda like a plastic, semi-inflated shopping bag floating on the top of the waves, don’t turn into Captain Cleanup and swim out for it. Chances are it’s a Portuguese Man o War, a fairly deadly type of jellyfish that, like an iceberg, is MUCH bigger under the water than what it looks like above it.
3. Strip Clubs–If you like to include adult entertainment in your vacation plans, KW has good (and some very bad) options.
The Good: Red Garter (208 Duval St) Across the street from Irish Kevin’s sits this gem of a gentlemen’s club. It’s clean, it’s not that expensive, and most importantly, the girls are pretty hot. Many (from what I’ve heard!) are from eastern Europe, and have the sexy accent to go with the sexy view. And ladies, we’ve found, no we’ve HEARD that it’s a perfectly fine and acceptable place for you to visit, with your man or on your own.
The Bad: Bare Assets (1029 Truman Ave) It’s no secret that strip clubs use sex to separate men from money. The good ones do it deftly and subtly. Bare Assets tries to do it with a sledgehammer. I must’ve had my idiot look on that night, because the bartender tried to give me the wrong change three separate times (really dude?), and several friendly ladies who stopped by to say hello between stage sessions tried to distract me so they could attempt to swipe bills from the tip stack under my beer bottle. Fail.
It’s easy to fall in love with Key West’s beauty, charm, and “why worry?” attitude. And it’s consistent. No matter what’s going on in the world, or how much you’ve changed since your last visit, returning there still feels as comfortable and natural as a great old pair of jeans.
And it doesn’t take long to get into the Key West flow, once you arrive. Be prepared: you’ll likely be engaged in friendly conversation with complete strangers, you’ll probably try a food or drink you’ve never had before, you’ll almost certainly be in the general vicinity of drunk people, and you may decide to get a tattoo. But all that is the easy part.
The toughest thing to do is leave.
Got a Key West story or tip to share? Lay it on us.