In just over an hour, you can be sipping a Rum Runner cocktail in Key West—or indulging in a slice of key lime pie—where the laid-back atmosphere is a balm to your cares. Home to the Conch Republic, Key West is part carnival, part tourist trap, part history. Once home to literary greats Ernest Hemingway and Tennessee Williams, and music legend Jimmy Buffett, the island is a state of mind, long populated by smugglers and scalawags. Here you’ll find the best of the Caribbean on U.S. soil, from tropical fish to bath-warm water, where the local dress code leans heavily on cargo shorts and flip-flops.
Departing From: Tampa International Airport (TPA)
Flight Duration: 1 hour, 7 minutes
Nonstop Flights: Daily
Airlines: Breeze Airways
Where to Stay
Your lodging choice depends on your mindset. Seeking total calm? Opt for a private cottage on Sunset Key, an island just offshore with its own ferry. Grab an Adirondack chair and a novel, wiggle your toes in the sand and breathe in the bougainvillea. Looking for action? Ocean Key Resort is steps from Mallory Square, with cheerful suites overlooking the water. Prefer beach vibes? Consider the Residence suite at Southernmost Beach Resort, save with Floridian discounts at Casa Marina, or laze at The Reach—all with private beaches.
Where to Eat
Start with breakfast at Blue Heaven (don’t miss the banana bread). Midday, try Sunset Pier for overwater snacks or The Breakfast Club, Too for one of 11 different Bloody Marys. Dinner calls for Prime Steakhouse, with surf and turf (10-ounce filet and 8-ounce lobster) paired with a nice red. Garbo’s Grill serves standout fish tacos, The Conch Shack has classic conch fritters, and of course, every meal should end with key lime pie.
What to Do
Check off the tourist classics: pose at the Southernmost Point, enjoy Mallory Square’s street performers, magicians and jugglers, and pub-crawl Duval Street starting at Sloppy Joe’s. Visit Hemingway’s House to pet the beloved six-toed cats, snap a selfie at Mile Marker 0 and explore the treasures at the Mel Fisher Maritime Museum and the nearby Shipwreck Museum.
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