Welcome to Southern Paradise. The Florida Key(s) to a Perfect Vacation

Editor, Amanda Stuermer

The Florida Keys

The Quick List

Looking for a surefire cure for the winter blues? Look no further than Florida. Whether you’re in the mood for a thumping party scene or vast stretches of white-sand beaches, you’ll find it in the Sunshine State. But ask a local where the best vacation spot is, and they’ll usually answer the Florida Keys. A 125-mile chain of islands flung south from the tip of Florida and connected by one narrow road and 42 bridges, the Keys are a veritable utopia.

Road Trip

It’s entirely possible to fly into Miami and drive to Key West in less than four hours, but we highly recommend tapping into your inner Southerner and taking your own sweet time so you can savor each and every juicy tidbit of charm that the Florida Keys have to offer, from tiki bars and beachside seafood joints to swanky boutique hotels and stunning nature preserves.

Key Largo

Start your slow roll in Key Largo. The chain’s first island offers 33 miles of sun-soaked beauty and underwater wonders. Key Largo is home to a spectacular reef system that includes John Pennekamp State Park, the first underwater preserve in the U.S., and the USS Spiegel Grove, a 510-foot landing ship dock intentionally sunk to create one of the world’s largest artificial reefs. Choose your adventure level: snorkel, dive, kayak, or take a glass-bottom boat tour. 

The Middle Keys

Just about halfway down the archipelago, in an area known as the Middle Keys, you’ll reach Marathon, a quiet beach town spread across 13 separate islands. Enjoy a relaxing seaside afternoon at Sombrero Beach or learn about the native wildlife at the Turtle Hospital, which rescues and rehabilitates endangered sea turtles, or the Dolphin Research Center, which educates on the area’s beloved dolphins and sea lions.

Key West 

You’ll end your journey in Key West, a town that covers approximately seven square miles and rests just 90 miles from the shores of Cuba—and embodies that wonderfully Southern mix of charming and quirky. It is unarguably the most famous Key, having once been the home to both Ernest Hemingway and Jimmy Buffet, who each wrote about and memorialized their island home in their very distinctive ways. And why wouldn’t they? Key West offers fabulous beaches, vistas, history, cuisine, music, and architecture for your ultimate pleasure. End your trip at the brightly painted buoy that marks the Southernmost Point of the continental U.S. (a quintessential photo op). We always say the journey is more important than the destination, but when Key West is your destination, it’s a toss-up.