Seven square miles of free-spirited magic drifting off the tip of Florida — Key West has a way of calling your name. Maybe it’s the pastel sunsets that look painted by hand, the tang of salt in the air, or the way time seems to stretch a little longer here, giving you permission to slow your pace. Maybe it’s the Conch Republic charm, where chickens roam freely, history hides in every lane, and the island’s come-as-you-are spirit wraps around you the moment you arrive.
Salt in the air, sunshine everywhere — welcome to Key West. (Photo Credit: Chase Baker)
And whether you’re staying on the island or making the easy day trip from Miami, this tropical outpost rewards every wanderer with its sun-splashed charisma. It’s a place where mornings start with Cuban coffee, afternoons drift into coral-reef adventures, and evenings unfold under strings of twinkling lights — always with a breeze, always with a story.
While we’re in full discovery mode, here are just a few reasons Key West keeps us completely captivated. From off-the-map cocktail dens to island adventures at the edge of the horizon, laid-back travelers will feel instantly at home here.
Sip the Island Spirit
On this island, cocktails are practically a cultural tradition. Two icons top the list: Sloppy Joe’s, a fixture since the day after Prohibition ended, and Green Parrot Bar, a gem that has been hosting poetry slams and tattoo contests since 1890.
Grab a bite and take in those sun-soaked moments that are worth slowing down for. (Photo Credit: Shomitro Kumar Ghosh)
But don’t miss the tucked-away favorites. At Virgilio’s Martini Bar, you’ll find perfect martinis and nightly live music. Alternatively, climb up to The Waterfront Brewery — home of the island’s highest deck — to sip local brews like a Belgian Sunburn IPA or Key Lime Gose. Pair small-batch wines with charcuterie at Viv Wine Bistro, then slip into General Horseplay, a speakeasy-style hangout known for glitter-kissed cocktails.
Dive Into the Blue
Just offshore lies the world’s third-largest coral reef, turning Key West into an aquatic playground. Watch wild dolphins arc through turquoise water on a dolphin safari, or drift across a remote sandbar and catch a technicolor sunset on a private charter.
Hop a seaplane to Dry Tortugas National Park and historic Fort Jefferson. (Photo Credit: Nick Rickert)
For the ultimate ocean escape, hop a seaplane to Dry Tortugas National Park, one of the most remote parks in North America. Snorkel living reefs, wander beaches of impossibly soft sand, and roam historic Fort Jefferson, the largest brick structure in the Western Hemisphere.
Wander the Tropical Streets
If you prefer to wander on land, Key West charms with lush foliage and an easygoing rhythm all its own.
Mallory Square is where sunset turns into a nightly festival of performers and buskers, while Southernmost Point is a concrete buoy and a can’t-miss photo op. Ernest Hemingway Home & Museum is filled with tropical gardens, literary lore, and six-toed cats. And, last but not least, Duval Street is a mile-long stretch of revelry lined with Bahamian and Spanish architectural gems.
Don’t miss the southernmost point in the continental US. (Photo Credit: Zoshua Colah)
And if you have extra time, explore beyond the main highlights — wander the quieter streets of Bahama Village, visit the Key West Butterfly & Nature Conservatory for a dreamy, kaleidoscopic escape, or take a bike ride beneath swaying palms to see the island at its most effortlessly enchanting.
Taste Your Way Through Key West
Begin your morning at Cuban Coffee Queen, a beloved local roaster. Order a “sunrise special” — half a Key Wester sandwich on pressed Cuban bread with a hot café con leche — and you’re well-fueled for the day.
Dinner choices range from upscale to wonderfully unfussy. Little Pearl plates dazzling day-boat catches like sautéed snapper and diver scallops. El Siboney, a beloved Cuban spot hidden from the Duval bustle, wins hearts with roast pork, fried yuca, and sweet plantains. At Moondog Café & Bakery, you could happily eat every meal: Breakfast tacos with chimichurri, lobster salad at noon, and a fisherman’s bowl filled with six types of seafood by evening.
Find beauty in every laid-back detail. (Photo Credit: Meg Von Haartman)
Dessert? It’s a whole scene. Think towering meringue-topped key lime pie at Blue Heaven, tropical homemade ice creams at Flamingo Crossing, and the sultry decadence of Better Than Sex, serving up playful creations like Cookie Nookie Pie and Peanut Butter Perversion.
Make It a Day Trip… or a Journey
Just a short drive or scenic flight from Miami, Key West makes for a breezy day trip when you want to trade city buzz for sun-soaked island life. The journey itself feels like part of the adventure — whether you’re cruising the Overseas Highway with endless water on both sides or soaring over patchwork reefs in a small plane.
Key West is a short drive from South Beach. (Photo Credit: Guzman Barquin)
Just another perfect day at the edge of the map. (Photo Credit: Lynn Danielson)
If the island wins you over (it tends to), consider stretching your stay. Key West has a way of loosening your schedule, slowing your heartbeat, and convincing you that one more sunset — or one more slice of key lime pie — is always worth it. So whether you’re popping down for the afternoon or settling in for a long weekend, this quirky, colorful paradise is ready to welcome you with cocktails, coral reefs, ocean breezes, and stories you’ll want to bring home.
Where to stay: Kimpton EPIC Hotel, Kimpton Surfcomber Hotel, Kimpton Hotel Palomar South Beach, or Kimpton Angler’s Hotel
