Key West, baby! We’d finally made it to the bottom of the 120-mile string of islands that make up the Florida Keys. After wildlife encounters in Fort Lauderdale, Key Largo, and Islamorada, we were excited to see what Key West had to offer.

So… do feral animals count as wildlife?? Bear with me, trying to keep with the theme… How about Key West’s wild night-life? I’m grasping at straws here, huh? Okay, out with the wildlife theme. Moving on…

Despite staying out wayyyyyy too late and drinking wayyyyyy too much the evening of our arrival (thanks for that, Sloppy Joe’s), we wanted to get-up-and-go bright and early on our first morning in Key West. (On that note, I was having some real trouble holding my camera still after the previous night’s debauchery. So lemme go ahead and apologize upfront for the shakey, Blair Witch-esque nature of the blurry photos you’re about to endure… pretty much throughout this entire post.)

We hopped on the bicycles we rented from Eden House, the inn we were staying at on Duval Street, and headed for what we thought would be a quick coffee and breakfast before touring the island. We were told Cuban Coffee Queen, a little coffee stand adjacent to the ferry terminal on the northwest side of town, was a Key West staple we shouldn’t miss. Little did we know it’d be a destination in itself!

Those feral animals I mentioned? Chickens. Pretty much the first thing newbies discover about Key West… there are chickens everywhere. Everywhere. It’s one of the things that makes Key West, Key West. Early residents brought them along for eggs and food and, over the years, some escaped and some were turned loose. Folks didn’t seem too bothered by it and, as time went on, a huge free-ranging population became the norm.

Huge as in thousands. All over town. On street corners, in the park, along the main drag, at the bars, on the waterfront and, on this day, at the coffee stand.

If you rely on me, in all my hungover glory, this is all you’d get ↑…

So, here’s an un-blurry smattering of what you’ll see ALL OVER Key West ↑ (Google search to the rescue… again!)

Rather than the quick breakfast we initially envisioned, we decided to spend some time with these local island residents. We snagged a picnic table and settled in. Y’all, fowl-watching is just as good as people watching. Call me lame, but it was yet another novel encounter for us and so much fun. Locals (of the human variety) may find them annoying after a while, but for a girl who doesn’t typically hang out with chickens at her average downtown coffee shop, they were pretty entertaining. How often am I gonna have my café con leche and Cuban cheese toast while cocks and hens strut around at my feet, chasing each other away from the imaginary morsels they’re pecking at? This is probably it.

On that note, Cuban Coffee Queen was an excellent recommendation. The java hit the spot and my cheese toast (white American, tomato and onions) was delicious. I’ll admit I was severely disappointed to see that it came slathered with mayonnaise (my nemesis in the food world), but it’s not their fault, I suppose. Apparently, you’re un-American if you don’t like mayonnaise. But, mayo on cheese toast?? Gotta say, though… despite my intense dislike of all things mayo, to my surprise it was actually freaking delicious. The toasted, cheesy goodness was just what I needed after a night that had left me fairly hungover. Mayo for… the win??

Another look inside my to-go bag revealed a dum dum! I got a kick outta that. Never been to a coffee place that serves suckers with their java… gimmicky, sure, but certainly memorable. It was just an all-around fun place to spend our morning.

Off we cycled down Duval Street, headed all the way (i.e. about a mile) to the opposite end of the island. Along the way, we passed by some famous Key West imbiberies like Sloppy Joe’s (hello, again), The Smallest Bar, and Fogarty’s Flying Monkey Saloon (where we stopped for one of their signature frozen drinks), before detouring a block to Whitehead Street to drop by Ernest Hemingway‘s house. From outside the gate, we were able to catch a glimpse of the gorgeous house and grounds, and even saw several of the famous six-toed cats roaming around (ick… sorry, not a cat person). But with a big enough line and a big enough entrance fee, we decided a tour of Hemingway house could wait till later.

We were off again, dialed-in to our destination – the famed buoy at the Southernmost Point. Despite having only been there since 1983, it’s become Key West’s most photographed spot. So, it was obligatory photo-of-Key-West’s-most-iconic-landmark time! Fun fact: this spot only marks the southernmost point of the continental US that’s publicly accessible by road. There are points in Florida that are farther south, and Hawaii’s Big Island is even farther south.

I’ll spare you the dozens of selfies we took. You’re welcome.

After getting our fill of photos, off we went again, taking a turn that led us through the super creepy Key West Cemetery before returning to Eden House to relax poolside for a couple hours. Just the rest we needed for the evening that awaited.

(We really enjoyed Eden House for it’s budget accommodation, location and daily FREE happy hour. Click here to see details and current rates. Or check below to compare rates for other Key West hotels.)

We got our second wind and ventured back out to stuff our faces at Blackfin Bistro for dinner. Of course, we then had to stop for more drinks at KW’s usual suspects – hello, Capt. Tony’s, and hello again, Sloppy Joe’s (seriously??).

Then, the day’s finale… we decided to hit up a drag show. Another “quintessentially Key West” thing to do, there were several options to choose from. We randomly settled on Aqua bar and nightclub. Part stand-up, part musical, and pretty much all lip-synched, it was nothing short of hilarious.

We had the pleasure of being entertained by Inga, Victoria and Elle. Inga, the lead Aquanette, kicked off the show in a ridiculous costume that featured gigantic eyeballs at her boobs and a moving mouth at her crotch. A mouth that happily accepted tips, BTW. She did a few ditties before a wardrobe change that had her in a fully-sequined Superman costume – which she totally rocked. She then “sang” several more covers with some lame-yet-super-catchy jokes sprinkled in between numbers.

Next up was Victoria, who kicked ass with her impersonation of Karen from the sitcom Will and Grace, and Dolly Parton singing 9 to 5. She circled the room accepting all the dollar bills patrons could manage to shove between her ginormous flannel-clad boobs.

Finally, teeny-tiny Elle came out and wowed the crowd with all her contortions. This girl was limber, y’all! She was full of jumps, splits, bends and twists that I can’t understand how she got into. It was one trick after the other after the other, with literally no rest in between. She danced… She twerked… She spun around until I was dizzy… I have no idea how a human being can have as much energy as she did.

The crowd got super into it. The audience was whooping and hollering, people were tossing out cash like their very lives depended on it, folks were grinding on the performers… To say it was a riot would be an understatement. It was some of the funniest shit I’ve ever seen.

We were seated smack in the middle of the dance floor, where we could have a ton of interaction with the entertainment. Don’t worry, though, for those who prefer to admire these beauties from a far, there’s plenty of booth seating lining the walls. Just make sure you share the experience with other cool people…

Most tables on the dance floor are four-tops, so parties of two or less will get seated together. You’d think this would make for a good time, right? It should… Half the fun of this kind of thing is experiencing it with other rando drag show virgins. But, wouldn’t you know our luck… We were seated with what were probably the two bitchiest visitors to the island that day. From the moment they arrived, all they did was talk shit to us about the seating arrangement (apparently, ours were better, despite the fact that we were all at the same table), and by the end of the night I was fuming at the injustice of having had such terrible table-mates (these things are enormously unjust when you’re tipsy, you see). Corrie, in a much more enlightened state of maturity than I, shrugged it off. But I’d been robbed of the opportunity to make new travel friends… oh, the humanity!

Okay, end of dramatic, drunken rant. Back to the show. Needless to say, we were thoroughly entertained by these dancing girls ladies queens. And, surprisingly, afterwards we found ourselves back at Eden House well before midnight. After the previous night’s imbibement it was good to be in at a decent hour, especially considering all we’d packed in… we started the day hanging out with chicks, ended the day hanging out with chicks, and had a ton of fun in between.

If you go

I’ll work backwards, here. Aqua was obviously the highlight. Smack on Duval Street (711 Duval, to be exact), it’s right in the thick of all the touristy spots. You can reserve seats online in advance or, for same-day tickets, just give them a call (305.294.0555). That’s what we did, and the super friendly guy (gal?) on the phone hooked us up. If you’re ever in Key West, this is a MUST DO. Just note that the show is lip-synched – both the songs and most of the monologues. As in, you won’t be seeing any original material. Didn’t bother me in the slightest, I only feel the need to say that because I heard some folks complain about it as we were leaving (total fuddy-duddies, if you ask me).

At night, go to Sloppy Joe’s for loud music and a rowdy crowd. During the day, go to The Smallest Bar to have a drink on one of only two barstools in the joint. And go to the Flying Monkey Saloon for a Monkey Slush in one of their souvenir cups.

Eden House was a great budget place to stay – they often run specials under $100/night (click here for details and current rates). Five blocks from Duval Street at 1015 Fleming, it was just far enough removed from the action that we didn’t have to hear it all night. The pool and gardens offer a super tropical respite from all the partying and drinking that you pretty much can’t escape – though, they have a free daily happy hour, so that doesn’t help much! Enjoy!