Between the migrating fauna to seasonal art shows and exhibitions, Key West in the winter has something to offer for culture-seekers to nature-explorers.
There is a reason that Florida is America’s favorite place to winter. When the temperatures cool down, Key West opens itself like a flower, welcoming in its seasonal visitors from migrating eagles to migrating snow birds. The southernmost key comes alive with natural wonder, as well as culture, from culinary fests to art shows.
Activities & Attractions
Fish Your Heart Out
Any Florida fisherman will tell you that the cooler season is actually the best time of year to fish, thanks to the diversity in the water. When cool winds blow from the north and the sun hides behind clouds you’ll likely catch the usual winter fish like sailfish and black fin tuna. When the sun comes out and the wind pulls some warmer currents from the south, you might be lucky to find some summer favorites too, like tarpon and bonefish. Wild Bill Sport Fishing offers custom charters based on your fishing desires and departs from Key West Bight Marina.
Relive the Works of a Local Art Legend
Starting in early December and running through to the end of January, the Custom House, a beautiful red brick architectural gem and award-winning museum in the heart of Key West, is featuring an exhibit on the works of the late Ferron Bell. Bell, who used to winter in Key West, is something of a local legend, with many longtime locals proudly owning at least one of his paintings, which are full of whimsy and word play. Expect beach scenes where the palm trees are replaced with paint brushes and a giant comb framing a couple of – what else? – beach combers.
Find Feathered Friends
In the cooler months, Florida is home to over 300 species of birds – some of which live in the area year-round, while some are just stopping through. Keep an eye out for the four-foot-tall great egret or the many birds of prey who winter here, like bald eagles, osprey, and red-shouldered hawks. For your best chance of catching a glimpse at any of these, birds try a private birding tour through the mangroves with Captain Victoria Impallomeni of Dancing Dolphin Spirits Charter, which can last anywhere from four to seven hours.
Festivals & Events
38th Annual Key West World Championships, 11/4–11
The world’s biggest and fastest offshore racing series brings powerboats to race at more than 100 miles per hour across Key West Harbor. The best place to watch these amazing nautical feats is from Fort Zachary Taylor Park.
Lighted Bike Parade, 12/5
During this unorthodox seasonal celebration benefiting Wesley House Toy Drive, riders deck their bikes out in colored lights and dress up in costume before taking to the streets en masse.
Key West Food & Wine Festival, 1/23–27
Now in its 10th year, this food and wine festival brings together the area’s best culinary artists, wineries, and breweries to create a sensational flavorful week.
Old Island Days Art Festival, 2/23–24
This open-air art show and market features fine artists from around the country. The vendors and exhibitors are masters of woodwork, pottery, oil painting, photography, and all kinds of art.
Annual Conch Blowing Contest, 3/2
This festival, now in its 57th year, holds a special place in the hearts of locals, who call themselves “conchs.” This contest involves individuals and groups blowing into the giant conch shells, trying to make the loudest, most sustained, and most unique sounds for the judges.