Is Winter a Good Time to Visit Key West?

Is Winter a Good Time to Visit Key West?

In the midst of the bitterly cold doldrums of winter, many people begin dreaming of a tropical getaway. Blue skies, warm sun, and soft sand are on the top of many travel lists in the months between December and March. With plenty of warm destinations to consider, should you plan to visit Key West in the winter? Here are some factors to consider.

Culture & Entertainment

With a laid back and off the grid culture, Key West is a melting pot of social, economic and ethnic classes of visitors and natives. Explore the history of the city, stroll The Old Island Days Art Festival in February, or enjoy a play at the Waterfront Playhouse, which puts on its best shows during the winter months. The 56th annual Key West House & Garden Tour is also back in February and March, giving visitors an inside look at the unique architecture and grandeur of some of the island’s historic residences.

During the peak travel season in Key West, Duval Street – the infamous main street of the island – is brimming with great food and libations, lively music, amazing street vendors and boutique shops full of unique and handcrafted items that you can’t find anywhere else. Walk, bike or take a pedi-cab or trolley up and down the strip to experience all that it has to offer.

Attractions And Crowds

Festivals and events are happening almost every week in Key West. January’s main events include the popular Key West Food & Wine Festival and Florida Keys Seafood Festival, while April brings the Conch Republic Independence Celebration and the Taste of Key West. In between these festivals, there are ongoing events for every interest, including concert and symphony series, free lecture series at Mel Fisher Maritime Museum, and even unique pop-culture events like the World Sword Swallower’s Day at Ripley’s Believe It or Not!.

If you enjoy the social scene and rubbing elbows with fun, like-minded visitors, winter is an incredible time to visit the island. While winter is a busy time in the Keys, the One Human Family mentality of the island finds strangers coming together, smiling and bonding over the simple things in life. Expect that getting around will be slower – no big city hustle and bustle here! – but instead of being impatient, visitors this time of year enjoy slowing down and taking in the beauty of the journey just as much as the destination.


When it comes to winter weather, there are few places in the continental U.S. as lovely as Key West. Temperatures are in the low 80’s, there’s very little rain, and the humidity is low. In December and January, evenings can be a bit on the cool side, with temperatures dropping in the low-to-mid 60s – but it’s still warmer at night in Key West than anywhere else in America during what’s normally the coldest time of year.

Key West is a wonderful adventure no matter what time of year you visit, but if you’re looking for an action-packed break during the cold of winter, the island will not disappoint!

Book your private air travel to Key West with Salt Island Seaplanes, and get a taste of luxury before you ever set foot on the island! Contact us at (239) 263-SALT (7258) to learn more or schedule your Naples to Key West flight today.

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