The Ultimate Guide to the Florida Keys
When it comes to vacation getaways, Florida is more than spoiled with options—whether you're the type that pines for a cosmopolitan city or wide swaths of white-sand beaches. But when you live in the land of vacation, where do you go for your escape? For many Sunshine Staters, the answer is to the Florida Keys.
As a kid growing up in Fort Lauderdale, this laid-back paradise was my family's getaway of choice. The appeal wasn't so much about the beaches (though, there's plenty of them) as it was the feeling of escaping to an undiscovered utopia. Here, you're surrounded by water in what seems like a million shades of blue. Nearly every wrong turn leads you to a shady swimming hole with views for miles, and if you venture out into the wild blue yonder, the underwater coral kingdoms are teeming with color and sealife. But while it may feel otherworldly in its beauty and seclusion, the real magic of the islands is their accessibility: Fly into Miami in the morning and you can be island-side chowing down on a fresh mahi mahi sandwich by lunch.
So What Are the Florida Keys?
Spilling out south from the Florida peninsula, this dreamy archipelago forms a trail of beauty that comprises hundreds of (mostly uninhabited) islands. Forty-four of those are connected via the Overseas Highway, a 113-mile road spanning from Key Largo to Key West—the most famous among the bunch. While each island is a worthy destination on its own, the draw here really is in the journey. While making your way south, you'll leapfrog from island to island via a whopping 42 bridges, including the famous 7-mile bridge. Make it to the end—and with character-filled Key West as its grand finale, you'll definitely want to—and you'll be closer to Cuba than you are to the Florida mainland.
Related: The 7 Best Islands in FloridaÂ
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When To Visit
With year-round balmy temperatures, the Keys draw tourists near and far every season. Wintertime is when the crowds descend, searching for the sweet spot in favorable temps and low humidity. But late spring or summer (if you can handle the sticky heat) is when you'll find the best deals. The same rings true for fall, but beware of hurricane season (most active between August and October) and be prepared with a backup plan should weather put a damper on your getaway.
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Where to Stay
The beauty of the Florida Keys is that, with an entire length that takes just over two hours to drive (if you're beelining it—which no one does), you don't have to park yourself in just one place. Each island has its own perks and personality, from laid-back Islamorada to the funky and at times raucous Key West. The best way to see the Keys is undoubtedly by car: Most visitors fly into Miami and experience the islands in succession, staying a couple nights here and there along the way. This conveniently makes for a vacation that unfolds nicely: You can first kick back and get some sun at the Bungalows Key Largo, an adults-only all-inclusive resort; amp things up with some waterbound fun in Islamorada (The Moorings is a dreamy place to post up); and round things out at a cozy B&B smack in the middle of the Key West action. With five distinct regions to explore—Key Largo, Islamorada, Marathon, Big Pine Key, and Key West—there's more than enough to round out a week (or more).
Related: Plan the Perfect Girlfriend Getaway to the Florida Keys
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What To Do: Key Largo
Kick off your Keys journey at the chain's first and longest island, offering 33 miles of sun-drenched beauty and an underwater dreamland that attracts explorers from across the globe. As the self-proclaimed Dive Capital of the World, Key Largo is home to an impressive reef system that includes John Pennekamp State Park (the first underwater preserve in the U.S.) and the U.S.S. Spiegel, a 510-foot landing ship dock that was intentionally sunk to create one of the world's largest artificial reefs. If you prefer to stay a little dryer while witnessing the area's aquatic wonders, Pennekamp Park also offers glass-bottom boat tours and kayak rentals.
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What To Do: Islamorada
Venture further south into the turquoise abyss and you'll hit Islamorada, a village of six islands beloved for its laid-back feel and sweeping vistas (it's starred in more than a few Hollywood productions, including Netflix's Bloodline). Here within the "Sportfishing Capital of the World," leaning palms frame views of calm blue-green waters dotted with activity: boats, paddlers, kayakers, swimmers. Islamorada is the perfect place to splash around yourself. From kiteboards to waverunners, the island offers multiple places to grab a rental. Post splash-session, take the kids to see the sealife: Theater of the Sea entices with dolphin encounters, and at tourist-fave Robbie's Marina, you can feed a school of more than 100 hungry tarpon (and their pelican friends). End your day with a rum runner at the island's world-famous Holiday Isle Tiki Bar.
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What To Do: Marathon
Right around the halfway point in the archipelago you'll hit Marathon, a quiet little city made up of 13 separate islands. Now's your chance to cash in on that R&R—Sombrero Beach is one of the best sandy shorelines around. When you've had your fill of surf and sun, get schooled on some of the Keys' native wildlife: The Turtle Hospital rescues and rehabilitates endangered sea turtles, and the Dolphin Research Center  educates on the area's beloved sea mammals (dolphins and sea lions). When you work up an appetite, Keys Fisheries is a must-stop whether you're parked for a few nights in Marathon or just passing through.
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What To Do: Big Pine Key
If you're here for the nature and could do without the crowds, Big Pine and the Lower Keys are a great place to settle in. Roughly 30 miles north of Key West, the islands are rife with low-key activity both on water and land, yet a quick (and beautiful) drive to all the action. Bahia Honda State Park offers it all: swimming, camping, fishing, boating, excellent birding, and even a hike that drops you off at the top of the Old Bahia Honda Bridge (with a bird's eye view of the entire island). And while it may be quiet, you won't need to look far for some sundown refreshments: Just drive the Overseas Highway and you'll find plenty of casual seafood-and-beer joints (No Name Pub is a perennial favorite).
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What To Do: Key West
You've made it to the end—but things definitely aren't slowing down. Measuring little more than 7 square miles, this famous Key (once home to authors Ernest Hemingway and Tennessee Williams) is packed with all the makings of a dynamite vacation: beaches, history, food, killer sunsets, and some really great bars. Once you post up at your home away from home, ditch the car in favor of two wheels and go out and explore. The Hemingway House is a charming glimpse of island architecture and the author's famous six-toed cats; the brightly painted buoy that marks the Southernmost Point of the U.S. is a beloved photo opp; and the watering holes along Duval Street will keep you occupied into the wee hours of the night. (Just make sure not to miss the sunset celebration at Mallory Square.)
Related: The 20 Best Things to Do in Key West