This past weekend, Alex and I took a tiny trip to Key West. Just two days and two nights, but as always it was just perfect. Only a few short months into dating, we did the same thing…and we are convinced that’s where we fell in love. So this trip is a really special one, and the Keys are near and dear to our hearts. If you’re looking to book a quick trip with your loved one, you’ve got to consider Key West.
Jimmy Buffet’s Margaritaville | I mean…a classic. You can’t go to Key West and not stop by Margaritaville. You may even need a shirt… I may or may not have one.
Schooner Wharf Bar | An outdoor bar/restaurant on the water in “old town” Key West. The band of older men is super sarcastic and entertaining, and shoes and shirt are definitely optional.
Ana’s Cafè Cubano | The tiniest of cafès, with the best Cuban sandwich! Alex died for their spicy Cuban, while I kept it original with their authentic. You will probably overeat because you can’t stop…
Sloppy Joe’s | One of my favorite places in all of Key West. The lunch menu is to die…and see below for the evening scene.
Sloppy Joe’s | Ahhh Sloppy Joe’s. Home to a plethora of mediocre cover bands that feature songs from every decade of life! The drink prices are good, and you will dance and sing the night away. Expect a sore throat the following day.
Fat Tuesday | A very, very close second favorite. You’ve probably heard of Fat Tuesday before…but no location compares to Key West. Their entire wall of blended adult beverages provides a thirst quench for any and all taste buds, and their music guarantees you’ll be booty poppin’ all night (or in my case, trying to). AKA what’s not to like?
Rick’s Bar | A two story indoor(ish)/outdoor bar who’s happy hour includes all you can drink for $15 from 9pm-12am… Need I say more?
Rent Mopeds | We really enjoy renting from HydroThunder, as they don’t break down on you (yes, some other companies do). Honestly, neither Alex nor I had done this before we met, and now it is our favorite thing about the trip. Take a tinyyy break from drinking, and explore the island by moped!
Smathers Beach | A super mediocre beach (however, I am spoiled by St. Pete/Clearwater), but the only real beach on the island. You have to go just to say you have…and if you go on the right day, the food trucks have some REALLY good crab cake sandwiches.
Booze Cruise | I think this is a must do! Take your pick of multiple cruises (each of which is only a few hours long) depending on whether you want to snorkel, dolphin watch, or simply enjoy the sunset from the water. All offering all you can drink, but only after you’re done with your swim (safety first!).
Drag Show | Judge me all you want…but don’t knock it till you try it! The drinks are super over-priced but the entertainment is prime. If you’re sensitive to dirty humor, this is not the place for you.
Southernmost Point | Literally a giant buoy that says “Southernmost Point” on it…because it is the southernmost point of the continental USA. There will be an obnoxiously long line for photos, so just stand a few feet away and take a selfie 🙂 It’s just something you have to do!
Still on my bucket list
Ernest Hemingway House | All I know is there are a LOT of cats and I’m sucker for an old American novelist…so obvi I will be checking this out.
Dante’s Pool Bar & Restaurant | Basically a Vegas pool party, but in Florida. I have yet to go but I’ve heard a million good things.
Key West is very casual… Unless you are going for Spring Break and just feel like being extra (which I definitely have been there, done that) you honestly can get away with wearing your swimwear and cover up anywhere and everywhere, at all hours. In fact, that’s all I wore this entire trip. But that’s one of the things I love about the island life! There’s no expectation except for you to show up and have fun. And I guarantee you will!
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