The Ultimate Guide To The Florida Keys

Reese Lassman/EyeEm/Getty Images
Reese Lassman/EyeEm/Getty Images

When it comes to vacation getaways, Florida spoils us with options—whether you're the type that pines for a cosmopolitan city or vast areas 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 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 are plenty of them). It is the feeling of escaping to an undiscovered utopia. Water surrounds you in what seems like a million shades of blue in the Florida Keys. 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 sea life. 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?

Reese Lassman / EyeEm / Getty Images
Reese Lassman / EyeEm / Getty Images

Spilling out south from the Florida peninsula, this dreamy archipelago forms a beauty trail comprising hundreds of (mostly uninhabited) islands. The Overseas Highway connects 44 islands, a 113-mile road from Key Largo to Key West—the most famous among the bunch. While each island is a worthy destination, the draw here is in the journey. While heading south, you'll leapfrog from island to island via a whopping 42 bridges, including the famous 7-mile bridge. Make it to the end—with character-filled Key West as its grand finale, you'll definitely want to—and you'll be closer to Cuba than the Florida mainland.

Related: The 7 Best Islands in Florida

When To Visit

photosvit / Getty Images
photosvit / Getty Images

With year-round balmy temperatures, the Keys draw tourists near and far every season. In wintertime, crowds descend, searching for the sweet spot in favorable temps and low humidity. But you'll find the best deals in late spring or summer (if you can handle the sticky heat). 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 the weather damper your getaway.

Where To Stay

Courtesy of Bungalows Key Largo
Courtesy of Bungalows Key Largo

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 in just one place. Each island has its 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 of nights here and there, conveniently making 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, then amp things up with some water-bound 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

What To Do: Key Largo

Stephen Frink/Getty Images
Stephen Frink/Getty Images

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—intentionally sunk to create one of the world's largest artificial reefs. Pennekamp Park also offers glass-bottom boat tours and kayak rentals if you prefer to stay a little dryer while witnessing the area's aquatic wonders.

What To Do: Islamorada

romrodinka/Getty Images
romrodinka/Getty Images

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 a few Hollywood productions, including Netflix's Bloodline). Within the "Sportfishing Capital of the World," leaning palms frame views of calm blue-green waters dotted with activity—boats, paddlers, kayakers, and swimmers. Islamorada is the perfect place to splash around yourself. From kiteboards to wave runners, the island offers multiple places to grab a rental. Post-splash-session, take the kids to see the sea life. 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.

What To Do: Marathon

Simon Dannhauer / Getty Images
Simon Dannhauer / Getty Images

Right around the halfway point in the archipelago, you'll hit Marathon, a quiet little city comprising 13 separate islands. Now's your chance to cash in on that R&R—Sombrero Beach is one of the best sandy shorelines. 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.

What To Do: Big Pine Key

John Duarte/Getty Images
John Duarte/Getty Images

If you're here for nature and could do without the crowds, Big Pine and the Lower Keys are great places 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. Drive the Overseas Highway, and you'll find plenty of casual seafood-and-beer joints (No Name Pub is a perennial favorite).

What To Do: Key West

romrodinka/Getty Images
romrodinka/Getty Images

You've reached the end—but things aren't slowing down. Measuring little more than seven square miles, this famous Key (once home to authors Ernest Hemingway and Tennessee Williams) has all the makings of a dynamite vacation—beaches, history, food, sunsets, and some great bars. Once you post up at 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. (Make sure not to miss the sunset celebration at Mallory Square.)

Related: The 20 Best Things to Do in Key West

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