For many South Floridians, the soul of Key West tends to elude us–is it old Florida? Is it our very own capital of debauchery? Before we started our latest Culture Crusaders journey to another neighboring Florida city, we began to notice something distinctly similar between the Southernmost Point and our own home. Much like Miami, this little treasure trove at the tip of our state has been mistakenly identified as ‘party town USA’, like a sub-tropical recreation of Bourbon ST. While that essence might still be there in some ways, we uncovered a whole world of historical gems preserved in time, a strong artisan and small business community, and the low-key way of life only the South can provide.
Video by VACO Studio.
We decided to challenge the stereotype and find all the things locals are proud of in Key West. If you’d like an easy-to-read breakdown, scroll all the way to the bottom of this piece. If you want to experience our journey of discovery, read along with our tips on how to embody the spirit of Key West like a local would:
Whether you’re driving from Dade or Broward, even a 2-hour drive tends to feel a little long. So we actually endorse exploring the smaller towns on the way down since some of the best spots are hidden among the exits. If you need a caffeinated pick-me-up, we love the oasis at Cafe Moka‘s new spot in Islamorada. It’s a little artist commune with a selection of boutiques and eateries, but the cafe churns out fresh-baked croissants, pastries, and of course, coffee. If you’ve worked up an appetite, you can’t pass off the classic, Alabama Jack’s. Or check out Keys Fisheries for their world famous Lobster Reuben.
We were lucky to check into the tropical cove that is Parrot Key Hotel & Villas, where a string of Old Florida-style houses have become one of Key West’s most breathtaking places to stay. The luscious collection of cabanas are filled with hidden corners and secret gateways to pure bliss…and four swimming pools. Greeted with freshly-made sangria, we made our way to our villa for the weekend, complete with its very own beach and hammocks for daytime lounging. Enjoy some downtempo disco beats while digging into yummy breakfast to get ready for the day. You can easily bring a whole crew of friends here for a getaway, not spend more than you would at a luxurious South Beach hotel, and be minutes away from some serious fun.
It’s hard to decipher what’s a tourist trap and what’s a local gem, so we’re here to help clear the noise. One good way to get the most out of your trip is by being as mobile as possible so you can cover a good amount of ground. We rented an electric golf cart (big enough for eight) from A&M Rentals and instantly felt like VIPs everywhere we went. They have bikes and scooters too, if you’re a smaller group, but either way, we never had to worry about hard parking situations and got to see much more of the town. Being more agile also lets you get acclimated and build a better sense of direction, which will come in handy after a few drinks later on.
The proximity of everything in Key West makes it easy to get around, explore and discover the easy way of life that Key West embodies. Sunny or not, it’s hard not to fall in love with Key West’s charm. The quintessential pastel-colored architecture broken up by vibrant bursts of bougainvilleas is wrapped in natural, tropical beauty–it’s a small-town vibe with a big city heart and a whole lot of character and spunk to go along with it.
We indulged heavily at the historically artistic commune that is Blue Heaven, a local’s favorite for their famous key lime pie (a favorite of country singer, Kenny Chesney’s) and old saloon atmosphere. The series of quaint cottages were transformed into an eclectic oasis and a popular meeting spot for drinks and live music, and you can even venture upstairs to see the brothel-turned-classy establishment where greats like Hemingway were regulars. Never say no to their special of the day, we were lucky to try their lobster BLT which was an easy winner.
Books & Books has a sweet literary nook down in the keys complete with an art supply store that serves as perfect respite from the heat or rain, and a great place to get inspiration at any time. Another nice gem for all-day sustenance is Moondog Cafe, right on Whitehead ST. Everything in this homey cottage is made in-house and they source their fresh-roasted coffee locally. The space is a perfect example of Key West’s resilience and strong community, opening as a result of Hurricane Irma by the same team behind the beloved Banana Cafe and The Cafe. It’s funny that you have to cross the breadth of Florida to feel like you’re truly in the south, where the shining hospitality of Georgia and Louisiana are still very much alive.
It’s impossible not to get lured in by the high-trafficked areas, so you might as well just embrace it at some point. Grab some sweet sweet goodness at Glazed Donuts right near the historical Tropic Cinema for a great photo op. Speaking of points, you’ll have to at least drive by the Southernmost Point buoy since it’s still a nice sight to see.
Nearby, we highly suggest popping into the Key West Butterfly & Nature Conservatory which, although unassuming, is actually the #1 attraction in Key West. We met with George, the passionate owner who shared his story and love for butterfly houses around the world. You’ll walk into an educational A/V immersion on all things wings, and see how the conservatory raises the species in their respective farms from their respective home countries and brings them all the way to Key West. Then, a massive greenhouse gives way to a tropical feast for the senses where birds, butterflies, moths and even the famous flamingo duo, Ret and Scarlet, live together in peace among the outside bustle.
You can pass by other essential historical points like the Key West Lighthouse, right across the street from another highly-visited landmark: the Ernest Hemingway Home and Museum. Built in 1851, the multi-level house was the writer’s escape for nearly eight years from 1931 – 1939 and has his second floor studio preserved just as he left it. While it might be crowded with curious tourists, we still like to come visit the cats on the property to make furry friends.
Catch a Waterside Sunset.
If you’re in need of some water action but don’t have the means to rent a boat for the day, like most of us, Fort Zachary Taylor Beach is a great option to get a good splash in. Walking along Key West’s streets, exploring the overgrown trees and cramped nostalgic architecture, you’ll say hi to a few roosters along your way to a sunset celebration at Mallory Square. The historical plaza comes alive every evening where locals and tourists come together to catch the light. Live music and dancing is a must while watching the sunset in Key West. Grab a fresh coconut while you enjoy the OG light show. As you take it all in, why not have a tarot reading while you’re at it?
Whether you head to traditional hangs like Pinchers or DJ’s for amazing crab and clams, you should make your way down the Mall on Duval on Fridays at 5pm where its 5, 6, and 700 blocks become a pedestrian walkway. You’ll find some of Key West’s busiest watering holes along Duval, like Caroline’s Other Side where you can enjoy craft cocktails in a Victorian house featuring a tap room and an array of patio games outside. Who knows, you might end up having a two-hour jenga match with a couple of Texans to kick off the night. Next door, explore the nighttime market where fresh guacamole and tacos mingle with tchotchkes and other crafts.
Step inside General Horseplay nearby, a slinky billiard bar with delicious pre-batched cocktails and occasional takeovers by some of Miami’s brightest bartenders. You can’t go to Key West and not check out Green Parrot for live music, where favorites like The Swayzees got their start. We caught the Grateful Dead cover band and they were insanely impeccable. They even casually played my request for “Shakedown Street” while we jammed with cheap tequila sodas in-hand, laughing about how easy it is to have a good time in Key West.
If you’re really taking advantage of the nightlife offerings around Key West, whether at Willie T’s, Sloppy Joe’s, or Captain Tony’s, you’ll eventually need to get some late-night munchies in that empty belly. We bit the bullet and went to Mr. Z’s in Old Town for their famous pizza and cheesesteaks only to continue our night out and about. Energy seems to come from nowhere when you’re making the most of your time, so we continued on, following strumming electric guitars along the way. Eventually, we needed a serious fourth meal at Mary Ellen’s and dug deep into some grilled cheese sammies and seasoned fries to end the night.
Cafe Moka – Intimate local coffee shop in a beautiful artisan oasis.
Alabama Jack’s – A classic seafood and BBQ spot that can’t be missed.
Keys Fisheries – A fresh-caught haven where lobster Reuben and hogfish are king.
Blue Heaven – A collection of eclectic cottages now serving some of the best, locally-sourced eats in town.
Moondog Cafe – A must-try for afternoon coffee, or breakfast, or lunch, or whenever.
Glazed Donuts – Delicious homemade donuts in a funky bakery.
Cuban Coffee Queen – One of Key West’s favorite coffee connoisseurs and roasters.
Mr. Z’s – A Late-night, no-frills pizza joint also serving cheesesteaks.
Mary Ellen’s – A sweet little dive with delicious fries and grilled cheese sandwiches.
Pinchers – Need a view? Pinchers is right on Duval and has a second floor that’s perfect for happy hour.
DJ’s Clam Shack – A Key West classic serving some of the best clams in town.
Date & Thyme Organic Market – It might be hard to eat healthy in Key West so this cute organic market is just the ticket.
Matheessen’s – An old school ice cream shop with cookies the size of your face.
Sloppy Joe’s – Easily one of the most well-known establishments in all of Key West.
General Horseplay – A slinky bar with high-class cocktails where bar takeovers from Miami favorites are not uncommon.
Caroline’s Other Side – A Victorian house-turned-tap room with patio games.
Willie T’s – Dollar-lined walls are popular at this bar serving cheap drinks and live tunes.
Green Parrot – The go-to late night spot for live music, pinball, and good drinks.
Captain Tony’s Saloon – Another bar high on the list of historical watering holes.
Point5 – An intimate upstairs bar serving great bites along with nice drinks.
Rick’s – It’s the gateway to some of Key West’s most entertaining bars.
Butterfly & Nature Conservatory – A beautiful escape from the craziness outside, complete with a greenhouse and thousands of butterflies and exotic birds.
Key West Lighthouse – Historical landmark boasting cottages on-site and of course, the original lighthouse.
Ernest Hemingway House & Museum – 170+ year old house where the famous author once lived, now a historical landmark.
Mallory Square – A waterfront plaza where street performers and pop-up vendors come together to make every sunset into a celebration.
Mall on Duval – A pilot program extended through November where three blocks on Duval street are transformed into a pedestrian walkway every Friday.
Fort Zachary Taylor Beach – A secluded beach away from the crowds where boats can dock and you can lounge.
Books & Books – Their Southernmost bookstore adjacent to an artist studio for supplies of all kinds.
Mel Fisher’s Treasures – A cool spot for anyone interested in shipwreck treasures.
Key West First Legal Rum Distillery – Free tours and samples? Oh yeah.
Southernmost Buoy – You got it.
Key West Aloe – A natural gift boutique with beauty products, animal treats, and so much more.
Tropic Cinema – Key West’s coolest cinema showing all kinds of films from mainstream to indie and beyond.
Need more recs? We barely made a dent in our itinerary, DM us on Instagram if you’re in need!
All photos by FujiFilmGirl. See full album here.