South for the Winter: The Best Time to Visit the Florida Keys

You probably know that the Florida Keys are a classic destination for “snowbirds” escaping the icy northern winter. But how much do you know about what a winter in the Keys is actually like? Here’s an overview of all that you can expect when visiting these enchanting islands in December, January, or February.

Perfect Weather

As the rest of the country cools down, the Florida Keys warm up: The average high is a balmy 76.1 degrees Fahrenheit in December, 74.8 degrees Fahrenheit in January, and 75.4 degrees Fahrenheit in February. The rainy season of early fall has also worn off by now (along with the attendant humidity), so the months between December and March bring minimal precipitation— an average of roughly two inches per month.

A Lively Atmosphere

It’s peak season in the Keys this time of year, and many of the eateries and dive bars that close up during the summer months roar back to life. Hit up spots such as the Tiki Bar at Holiday Isle or The Lorelei Restaurant and Cabana Bar for tasty seafood, refreshing tropical cocktails, and world-famous sunset views. The scene at shopping centers from the Rain Barrel Artisans Village to the Mallory Square also picks back up; it’s a perfect time to search for that perfect Key-lime-pie mix or a lovely ocean-inspired painting.

Exciting Events

The best time to visit the Keys is December, when lit-up boats sail over the Key West Bight and Harbor, Key West Old Town holds the “Holly Jolly Holiday” trolley, and Christmas shows, Nutcracker performances, and holiday concerts takes place. Other events throughout the winter, mainly down in Key West, run from the annual car show to the New Year’s conch drop to the January Literary Seminar and Food & Wine Festival.

Ready for a winter getaway? Browse the accommodations at Cheeca Lodge & Spa and start planning your trip.

Driving the Florida Keys: Everything You Need to Know

The Florida Keys are one of America’s most famous road trip destinations. Here’s what to know before you hop in your rental convertible and take on the 113-mile Overseas Highway for yourself.

Iconic eateries

You’ll be confronted with so many seafood restaurants that you won’t even want to finish making it to Key West. Hungry Tarpon, Wooden Spoon, Lazy Days Restaurant, and Mrs. Mac’s Kitchen are just a few spots known for the region’s delicious seafood, as well as hearty desserts. Fun, kitschy decor also characterizes many of these restaurants, like dollar bills, license plates, and surfing-related gear, so feast your eyes as you savor the signature conch fritters or Key-lime pie.

Iconic bars

Piña coladas and margaritas are as much a Florida Keys staple as the aforementioned seafood snacks. In the course of planning your itinerary, or simply drifting down the highway at your comfortable pace, prepare to encounter storied dive bars from Alabama Jack’s to No Name Pub (many with their own eye-catching decor). For a local beer in lieu of the requisite margarita or piña colada, try the Florida Keys Brewing Company, hosting tours and tastings.

Unexpected attractions

Prepare to see incredible attractions unlike anything you’ve seen elsewhere, like the massive Seven Mile Bridge, the Robbie’s Restaurant tarpon pier, the giant lobster sculpture at the Rain Barrel Artisan Village, and a hospital dedicated to rehabilitating rescued turtles. The History of Diving Museum is another one-of-a-kind spot, as the world’s largest collection of diving-related artifacts, like bell helmets and cameras for underwater photography.

Beautiful scenery

One of the best parts of a Keys road trip is the amazing scenery. As you make your way south, stop at Anne’s Beach, Bahia Honda State Park, and Morada Bay for soft sands and crystal-clear waters, and John Pennekamp State Park for boat rides around snorkeling spots with lush coral reefs. And don’t miss the world-famous sunsets, either: Grab a Gulf-facing seat at the Lorelei Restaurant and Cabana Bar or embark on one of the Keys Sunset Sails.

If you need a place to rest up during your Florida Keys road trip, check out the exclusive offers at Cheeca Lodge & Spa.