Plan the Perfect Florida Keys Vacation

Discover a tropical paradise without ever leaving the United States: The islands of the Florida Keys are all situated within easy reach of the mainland. Home to some of the most picturesque beach towns in the world, the Keys offer a truly unique vacationing experience that rivals the Caribbean. Spanning a stretch of around 115 miles and connected by a series of impressive bridges, this vast archipelago is best explored via car over the course of several days.

After a brief period of rebuilding, the Keys are now officially up and running with all remnants of last year’s hurricane cleared away. There has never been a better time to immerse yourself in the breezy beach town mindset of these island communities. Use this guide for inspiration while you plan your visit.

First Stop: Key Largo

The most well-known of the northern Keys is Key Largo. Found just about an hour and a half outside of Miami, Key Largo is known for housing North America’s only barrier reef, which happens to be one of the largest in the world. Explore the breathtaking reef during your stay in Key Largo while snorkeling or scuba diving at the John Pennekamp Coral Reef State Park. Animal lovers will delight in the variety of marine life found in the reef.

Second Stop: Islamorada

Next on your journey down the Keys should be Islamorada. Found in the middle Keys, Islamorada offers a one-of-a-kind island experience enveloped in a distinct island vibe. From relaxing on the amazing and secluded beaches, feeding massive tarpons at Robbie’s Marina, or sampling the best local brews at the Florida Keys Brewing Co., there is something for adventure-seekers of all kinds.

With so much to do in Islamorada, you’re guaranteed to want to stay more than just one night. For a relaxing home in the Keys, Cheeca offers casually elegant accommodations and calming amenities right along the water. End the day watching an unforgettable sunset in Morada Bay, less than 10 minutes walking from Cheeca. For more information, or to book a stay at Cheeca, visit or call (866) 853-9338.


Next Up: Marathon

Continue your Florida Keys road trip, making sure to stop in Marathon Key. About an hour from Islamorada, Marathon offers its own special take on life in the Keys. One of the top attractions in Marathon is the famed Turtle Hospital, sure to be a heartwarming stop on your journey through the Keys. Marathon also offers visitors countless beaches to relax and explore, including the historic Pigeon Key.

Last Stop: Key West

After making it across the Seven Mile Bridge—the longest bridge in the Keys—you aren’t far from the farthest and final Key: Key West. Outdoor adventure, great eats, and beachside relaxation await visitors of Key West. Scuba dive 100 feet below the ocean’s surface while you explore the Vanderberg Shipwreck, the second largest in the world, or dine at a local classic, Banana Café, known for their sweet and savory crepes.

Whether you plan to visit for a couple days or want to explore the islands for a week or more, we recommend hopping in your car—or flying into MIA and picking up a rental—to uncover the best of the Keys.


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