Skip to Content

Things to Do in Key West in January

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!

360 Degrees on the Water

Group of people enjoying a jet ski tour in Key WestAll 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 12-15

The Key West Literary Seminar is holding its 35th annual conference at the San Carlos Institute on Duval Street with the theme “Revealing Power: The Literature of Politics.” Top literary luminaries in attendance include Teju Cole, Gail Collins, Joyce Carol Oates, George Saunders and Curtis Sittenfeld for a long weekend of readings, panel discussions and cocktail parties.

Lace up Your Running Shoes

January 15

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.

So Many Sailors!

January 15-20

The 30th Annual Quantum Key West Race Week is back featuring world-class sailing and yachting teams from more than 12 countries and 24 American states. More than 100 racing yachts compete for class championships in this international regatta. It’s an exciting week with beautiful sailboats docked in local marinas and racing offshore.

Conch Cottage Delights

January 13-14

Still going strong, the 57th 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 14-15

There’s nothing like fresh seafood straight from the source in Key West and the 12th 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.

Calling All Anglers

January 21-22

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.

Foodies in Paradise

January 25-29

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.

Save 10% using code: ONLINE
Dolphin Watch Eco Tour Eco Tour • Backcountry Snorkel
  • 9:00am, 12:30pm
  • 3 hrs
  • low
  • Beverages
Save 10% $67.46 Reg. $74.95
TRIP DETAILS BOOK TRIP
Save 10% using code: ONLINE
Dolphin Watch Sunset Cruise Combo Eco Tour • Backcountry Snorkel • Sunset
  • 5:00pm
  • 3 hrs
  • low
  • Beverages
Save 10% $67.46 Reg. $74.95
TRIP DETAILS BOOK TRIP
Save 10% using code: ONLINE
Double Dip Snorkel Sunset Combo Snorkel 2 Reef Locations
  • 5:00pm
  • 3 hrs
  • moderate
  • Beverages
Save 10% $44.95 Reg. $49.95
TRIP DETAILS BOOK TRIP
Save 10% using code: ONLINE
Double Dip Snorkel Trip Snorkel 2 Reef Locations
  • 9:00am, 12:30pm
  • 3 hrs
  • moderate
  • Beverages
Starting at $36.85 Reg. $40.95
TRIP DETAILS BOOK TRIP
Save 10% using code: ONLINE
Glass Bottom Boat Reef Eco Tour
  • 12:00pm, 2:00pm
  • 2 hrs
  • low
  • Snack Bar
Save 10% $38.65 Reg. $42.95
TRIP DETAILS BOOK TRIP
Save 10% using code: ONLINE
Glass Bottom Boat & Sunset Cruise Reef Eco Tour
  • 6:00pm
  • 2 hrs
  • low
  • Snack Bar
Save 10% $43.15 Reg. $47.95
TRIP DETAILS BOOK TRIP
Save 10% using code: ONLINE
Island Adventure & Sunset Cruise Combo Eco Tour • Snorkel • Kayak • Paddleboard
  • 3:30pm
  • 4.5 hrs
  • moderate
  • Food & Beverages
Save 10% $98.95 Reg. $109.95
TRIP DETAILS BOOK TRIP
Save 10% using code: ONLINE
Island Adventure Eco Tour Eco Tour • Snorkel • Kayak • Paddleboard
  • 9:30am
  • 4.5 hrs
  • moderate
  • Food & Beverages
Save 10% $89.95 Reg. $99.95
TRIP DETAILS BOOK TRIP
Save 10% using code: ONLINE
Key West Snorkeling Morning Reef Snorkel
  • 9:30am
  • 3 hrs
  • moderate
  • Beverages
Save 10% $36.85 Reg. $40.95
TRIP DETAILS BOOK TRIP
Save 10% using code: ONLINE
Key West Sunset Cruise Sunset Cruise • Champagne
  • 6:30pm
  • 2 hrs
  • low
  • Beverages
Save 10% $38.65 Reg. $42.95
TRIP DETAILS BOOK TRIP
Save Up To $8
Land and Sail Package Trolley Tour • Sunset Sail
  • low
$76.40 Reg. $84.90
TRIP DETAILS
Save Up To $14
Land and Sea Package Trolley Tour • Glass Bottom Boat
  • low
$63.81 Reg. $77.90
TRIP DETAILS
Save 10% using code: ONLINE
Reef & Ritas Snorkeling Trip Afternoon Reef Snorkel
  • 1:00pm
  • 3 hrs
  • moderate
  • Beverages
Save 10% $43.15 Reg. $47.95
TRIP DETAILS BOOK TRIP
Save 10% using code: ONLINE
Rum & Reggae Afternoon Reef Snorkel • Sunset Sail
  • 5:00pm
  • 3 hrs
  • moderate
  • Beverages
Save 10% $44.95 Reg. $49.95
TRIP DETAILS BOOK TRIP
Back to top