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 and jet skis. A delicious lunch spread & unlimited beer, wine, sodas & water are also included!



Ultimate Express

Thrills at 100 smiles an hour

Don’t have all day, but want to have all the fun? Climb aboard the Ultimate Express for an action-packed 3 1/2 hours on the water. From Jet Ski tours to banana boat rides, we make sure to pack in all the fun and excitement that Key West watersports enthusiasts love.



Fury group on jet skis in Key West

360 Degrees on the Water

All Month Long

The first thing on anybody’s Key West To Do List should be getting out on the water. With Fury’s 360 Jet Ski Combo Package, you can do this in more ways than one. First, get the lay of the land from the water with Fury’s 90-minute Jet Ski tour around the island. Then add up to two more water adventures, including Glass Bottom Boat, Snorkeling or Parasailing, for one low package rate. You can do all the trips in one day or spread them out over the course of your vacation.

Southernmost Literary Festival

January 9-12

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.

Calling All Anglers

January 16-19

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 17-18

Still going strong, the 60th 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.


Fresh Seafood

Fresh Catch

January 18-19

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.

Lace up Your Running Shoes

January 19

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 26-February 2

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 12/19/2019