Ahoy, sun-seekers and mojito believers! If you’re dreaming of a salty breeze, a buzz from more than just sea air, and waking up just in time for brunch (the most important meal of the day, obviously), then buckle up, buttercup. I just spent three days in Key West and I’m here to lead you—not to salvation—but to the strongest rum punch and the best damn Key Lime Pie you’ve ever tasted.

So, let’s do this. Three days. Zero regrets. 100% good vibes.

Day 1: "Sun’s Out, Rum’s Out" – Welcome to the Party

🏝 Morning: Banana Cafe
Touch down, drop your bags, and head straight to Banana Cafe. This French-inspired breakfast spot is everything—quaint, cozy, and serving crepes so good they might make you leave your partner for a Parisian chef. I had a mimosa and a ham & cheese crepe that whispered sweet nothings to my hangover from last week.

🕶 Afternoon: Exploring Old Town + Sneaky Cocktails
You better be ready to day drink! Wander Duval Street like you own it. Duck into shops, get your picture with a rooster (they run this island), and slip into Willie T’s for an adult beverage under a ceiling full of dollar bills. It's like a jungle bar and a cash explosion had a baby. Only good vibes! You will love it. Make your way to Irish Kevin’s for a big party inside with music, great Ruebens and cold beer! Come prepared to party and sing along.

🍹 Evening: Sunset Pier + Mallory Square
Golden hour is non-negotiable. Make your way to Sunset Pier, grab a frozen cocktail (I recommend anything swirled), and find a spot to watch the sky show off. Afterward, join the chaos at Mallory Square—jugglers, fire-breathers, a guy balancing a cat on his head… you know, standard pre-dinner entertainment.

🎤 Night: Sloppy Joe’s + Green Parrot + the rest is fuzzy…
The night's still young, and you’re headed to Sloppy Joe’s, Hemingway’s old haunt. Live music, dancing, and the kind of drinks that make you text your ex or tip your bartender $50. Then keep the buzz rolling at the legendary Green Parrot—no frills, all fun. There may or may not be a dog on the bar stool next to you. Rumor has it we made it to Tiki Bar, 801 Bourbon Bar, Old Town Tavern and Beer Garden,,,, Let the Advil kick in (Please!)

Day 2: “Brunch, Beach Bars, and Bad Decisions”

🍳 Brunch: Blue Heaven
Wake up (slowly), put on something loose, and strut over to Blue Heaven. Roosters will literally strut with you. Order the Lobster Benedict and a Bloody Mary that bites back. You’ll sit under a tree, listen to live music, and wonder if you can move here and raise goats or something.

🌊 Afternoon: Beach Time + Captain Tony’s Saloon
Walk it off on Smathers Beach or rent a bike and coast lazily along the waterfront. Then cool off the island way—with a cold drink in an old bar. Captain Tony’s is the dive bar of your dreams. Walls made of history, bras hanging from the ceiling, and possibly haunted (but in a flirty ghost way). Meander over to Schooner Wharf Bar to watch people age dis-gracefully with live music and cold drinks! For the wild ones, walk down to Dante’s for fun in the pool then tip toe out once you have seen or shown more than you anticipated!

🍽 Dinner: Local Seafood + Live Music at Hog’s Breath
Fresh fish is a must. Try Conch Republic Seafood Company for a sunset meal, then head to Hog’s Breath Saloon. Great music, stiff drinks, and a sign that says “Hog’s breath is better than no breath at all”—and honestly, they’re not wrong.

🌛 Late Night: Duval Street Crawl (Again)
You’re a seasoned pro by now. You are on vacation, grab a dessert at Better than Sex! Hit a new round of spots or revisit your favorites. This time, chat up the band at Willie T’s (our favorite), challenge a stranger to a dance-off or drink off, and take too many selfies. It’s all part of the plan. Okay… fuzzy again! Sounds like we were spotted in the wild at Hanks Hair of the Dog Saloon off Duval on Caroline Street. We saw a woman going crazy on Caroline Street! Somehow we made it to Rum Bar.. couldn’t tell you what it looks like!

Day 3: “Recovery Mode… Kinda”

🍉 Brunch: Cuban Coffee Queen + Chill
Ease into your day with a Cuban coffee and a breakfast sandwich from Cuban Coffee Queen. You’re gonna need that cortadito to feel human again. Sit by the marina and contemplate your life choices (you'll be proud of most of them).

🐟 Afternoon: Waterfront Wandering + Local Vibes
Stroll the Key West Historic Seaport, check out the boats, and maybe hop on a quick snorkeling or dolphin-watching tour. Or don’t. No pressure. You’re on island time now. Duck into Half Shell Raw Bar for oysters and beer if the mood strikes (spoiler alert: it will).

🍹 Final Cocktail: Back to Sunset Pier
Your last night deserves one more magical sunset—and maybe one more piña colada. Toast to yourself, your carefree spirit, and the fact that you still remember your hotel room number.

Day 4: “Yes, it was supposed to be three days!”

🍉 Breakfast: Banana Cafe + Chill
Before heading to the airport, we popped into Banana Café for a delicious Frency Egg Sandwich and a Bloody Mary. Turns out the flight was oversold, and they wanted volunteers! We raised our hands to volunteer since we like to help people! And why not just stay one more day in Paradise. We grabbed a ride back to the hotel and got another night. We eased into the day to avoid a hangover the next day with another Bloody Mary at Rams Head. They have an incredible Bloody Mary bar. Good enough for us to quickly forget about easing into the day and worrying about a hangover…  

🐟 Afternoon: Adventure + Local Vibes
Boat or fly over to Dry Tortugas for a whimsical afternoon with breathtaking views and marine life. Everyone should take advantage of this beauty!

🍹 Final Dinner + Cocktail:
Your last night deserves one more magical evening, great dinner —and maybe one more adult beverage. Boat over to Latitudes

 

Final Thoughts:

If you came to Key West looking for enlightenment, you might’ve just found it in the bottom of a rum runner. But hey, life’s too short for weak drinks and boring vacations. So, pack light, tip heavy, and laugh loudly.

And remember: What happens in Key West… ends up in your group chat.

Catch you at the next tiki bar.
Love & hangovers,
Flip Flop Culture Krewe