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 Action Packed Excursion

Our most popular day on the water just got even more exciting! Check off all your vacation bucket list goals on this action packed trip. The Ultimate Adventure H2.0 has everything you can do on the water such as parasailing, jet skiing, a banana boat ride and Key West’s largest ocean water park! Refreshing snacks and unlimited refreshments are included to make this full-day excursion a once in a lifetime experience.

Haven’t had enough fun on our Ultimate Adventure H2.0? Hop aboard one of our many Key West snorkeling tours for the Ultimate experience.

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Southernmost Literary Festival

January 11th – 14th

The Key West Literary Seminar is holding its 41st annual conference at the Coffee Butler Amphitheater with the theme “Florida: The State We’re In” Keynote Speaker Jeff VanderMeer will be in attendance for a long weekend of readings, panel discussions and cocktail parties.

Calling All Anglers

January 11th – 14th

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 Oceans Edge Resort & Marina.

Fresh Seafood

Conch Cottage Delights

January 12th & 13th

Still going strong, the 64th 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.

Fresh Catch

January 13th & 14th

There’s nothing like fresh seafood straight from the source in Key West and the 18th 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.

Lace up Your Running Shoes

January 14th

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 23rd – 28th

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.

Last Updated 01/25/2024