Escape the winter chill and head south in January to enjoy Key West’s beautiful subtropical climate. It’s one of the most popular times of the year to visit and you’ll never be at a loss for something to do. That includes plenty of time for poolside relaxation, of course!

Ultimate Adventure

Key West’s Original All Day Excursion

Our Ultimate Adventure is a must do when you’re in Key West! Experience sailing on our 65′ catamaran in the Gulf of Mexico while enjoying breakfast as we take you to our coral reef to spend the day snorkeling & swimming in the turquoise waters. Afterwards, we set sail to the only state certified water park where you can enjoy multiple water toys, parasailing, banana boat rides and jet skis. A delicious breakfast & lunch spread & unlimited beer, wine, sodas & water are also included!

Calling All Anglers

January 14-17

Join the Key West Kingfish Mayhem tournament and troll for some of the biggest kingfish of the season. With a 50-boat field, the winning purse could be up to $15,000. The tournament is headquartered at the Stock Island Marina.

Conch Cottage Delights

January 15-16

Still going strong, the 61st Annual Key West House & Garden Tours take visitors through elegant and unique private homes in Key West, ranging from conch cottages to Victorian mansions that have all been lovingly preserved and restored with interior design that wows. It’s a true inspiration for anyone who’s ever dreamed of living in Key West.

Fisherman's Cafe lunch options

Walk Up Delights at Fisherman’s Cafe

The perfect spot, located on the way to the Historic Seaport, to eat a delicious and filling breakfast or lunch before heading out for the day. We suggest the “El Cubano” for breakfast & Lobster Enchilau Tacos if you’re stopping by for lunch.

Lace up Your Running Shoes

January 17

Recognized by Runner’s World magazine as one of the 10 great half-marathons of the winter season, the Key West Half Marathon follows a 13.1-mile course that snakes through Old Town Key West and the scenic waterfront. There’s also a 5K race for runners not quite ready to tackle the Half Marathon.

Foodies in Paradise

January 27-31

Celebrate the flavors of the Keys and the area’s top chefs with the return of the Key West Food & Wine Festival. The weekend consists of special dinners, grand tastings, neighborhood wine strolls and seminars for the hungry traveler.

Fresh Seafood

Fresh Catch


There’s nothing like fresh seafood straight from the source in Key West and the 15th Annual Florida Keys Seafood Festival is a celebration of this. Come out to Bayview Park for all the hogfish, spiny lobster, grouper, crab legs and oysters on the half shell that you can dream of. There will be live music and marine-themed crafts for the little ones.

Southernmost Literary Festival


The Key West Literary Seminar is holding its 38th annual conference at the San Carlos Institute on Duval Street with the theme “Reading between the Lines: Sports & Literature.” Top literary luminary Geoff Dyer will be in attendance for a long weekend of readings, panel discussions and cocktail parties.

Last Updated 01/05/2021