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. Soul Shine Charters offers custom private fishing charters in increments of four, six, and eight-hour tours and departs out of the Garrison Bight Marina.

Old Town Trolley's Holiday Lights & Sights Tour

See the Southernmost City All A-Twinkle

Key West is known for being festive year-round, but come the holidays, the island really outdoes itself with themed décor around every corner. We’re talking twinkle lights and tinsel wrapped around the palm trees up and down Duval Street, the historic homes in Old Town, as well as the boats in the various marinas. The best way to take it all? Book a special holiday lights tour with either Old Town Trolley or the Conch Tour Train, which during select nights during the month of December, chauffeur visitors through various island neighborhoods to take in the splendid spectacle over hot cider and cookies.

Peruse Art Created by Local Key West Ladies

From January right into early spring, the historic Custom House Museum hosts “From A Woman’s Hand.” Created by and for women, the exhibit features paintings, sculptures, textiles, photographs, and much more produced exclusively by the diversely talented female artists of the Florida Keys. The goal? To shine a light on gender inequality in the art world.

Festivals & Events

39th Annual RWO Offshore World Championship Powerboat Races, 11/3–10

The world’s biggest and fastest offshore racing series brings powerboats to race at more than 100 miles per hour across Key West Harbor.

Lighted Bike Parade, 12/4

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

Key West Food & Wine Festival, 1/26–2/2

Now in its 11th 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, 2/22–23

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.

Key West Conch Blowing Contest

Annual Conch Blowing Contest, 3/7

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.

Where to Stay Sunset Key Cottages | The Laureate Key West