Picture this: you’re nibbling on a sponge cake, watching the sun bake, with all of those tourists covered with oil; you’re strummin’ your six string on your front porch swing, and you smell those shrimp—they’re beginning to boil. Yes, these are the opening lyrics to the iconic 1977 hit “Margaritaville” by Jimmy Buffett, but they could also be your life, should you choose to accept it. Even before Buffet sang about his languid days spent in Key West, artists, writers, and vacationers were venturing to the Florida archipelago to sip on margaritas and watch the magnificent sunsets. Why not you, too? Below, the best places to eat, drink, stay, and go in the Florida Keys.
What to See
The Hemingway Home & Museum
Three words: six-toed cats. The famous writer’s Key West residence has been transformed into a museum, but the best part is that the grounds are roamed by about 60 cats, some of whom are descendants of Hemingway’s own polydactyl pet, a cat named Snow White. Go for the Hemingway history, stay for the cats.
Duval Street
The heart of old-town Key West, Duval Street is packed with bars and restaurants boasting live music every night, along with plenty of novelty shops to peruse once your Rum Runner kicks in.
Luna
Around the corner from flashy Duval Street sits Luna, a lovingly curated boutique that’s only been open a few months, but features some of the chicest clothing, accessories, and décor we saw on the island.
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Dissh Sienna Knit Midi Dress
Larroude Miso Platform Sandal
Where to Eat
Blue Heaven
If you ask a local the best place to eat in Key West, there’s a pretty good chance they’ll point you to Blue Heaven. The casual outdoor/indoor brunch and dinner spot started by a writer and an artist back in the ’90s serves delicious Florida-Caribbean fare like fresh fish, Jamaican jerk chicken, and shrimp and grits. Make sure you leave room for the sky-high key lime pie.
Santiago’s Bodega
A cozy tapas bar tucked away on a side street in Key West’s Bahama Village, this is a great place to grab a few drinks and graze on some snacks, like fresh tuna ceviche and patatas bravas smothered in chipotle aioli.
The Dining Room
The biggest restaurant at Little Palm Island, a private island resort, The Dining Room offers beachside dining with stunning views of the sunset. If you’re lucky, a key deer might even come to say hello during your meal.
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Where to Drink
Sunset Pier at Ocean Key Resort & Spa
Like most of Key West, Sunset Pier is casual and laid-back—the perfect place for sipping a mojito at sunset. They also have live music nightly, so you can listen to the waves and Jimmy Buffett covers.
Two Friends Patio Restaurant
Even if you don’t like to do karaoke, you’ll like Two Friends for the entertainment factor alone. It’s vacation—feel free to make a bit of a fool of yourself with an acapella rendition of “Halo”—or, better yet, watch someone else do it.
Berlin’s Speakeasy
Berlin’s is a classic cocktail bar and lounge for when you’re feeling like you’ve had enough of a taste of the “Margaritaville” vibe. Try the key lime pie martini for a taste of the keys.
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FP Beach Mykonos Fauxchet Sweater Mini
Dolce Vita Novah
Where to Stay
Little Palm Island Resort & Spa
Move over, Hawaii and Italy: this should be the next filming location for The White Lotus. The Little Palm Island Resort & Spa is situated on a private island accessible only by boat (and seaplane, if your budget can manage it), and features beautiful luxury bungalows with private beaches and an outdoor soaking tub the size of your first studio apartment. Tanya would love it.
The Marquesa Hotel
If you’re looking for more of a B&B vibe, the Marquesa has you covered. The boutique hotel transformed the 19th century “conch” houses on its property into private bungalows, but the real star of the show is the property’s obese cat, Bob, who’s always down to share a meal with you.
Winslow’s Bungalows
If a name brand property is more your thing, Kimpton’s Winslow Bungalows is the perfect mix of quirky Key West and luxury boutique hotel. It’s also pet-friendly, so you don’t have to spend your whole vacation missing your dog.
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Beauty Picks
about-face Cherry Pick Lip Color Butter in Dragonfruit Fusion
Get into this haute pink that looks good across all skin tones. This comfy, glossy lip color is uber pigmented with just one swipe.
MAC MACStack Waterproof Mascara in Blackstack
This waterproof mascara comes with a wand that perfectly separates each lash. The formula doesn’t clump and will stay on no matter how many dips you take in the ocean.
MDSolarSciences Gleam and Glow SPF50
This sunscreen-moisturizer mix is developed by derms. The formula not only protects your skin from the sun, but also nurtures it as it contains ceramides to protect your skin barrier, niacinamide to combat hyperpigmentation and wrinkles, and antioxidants to fight free radicals and environmental pollution.
