Ah, February—the month when the rest of the world is locked in winter’s icy embrace, but Key West is like that one person who just won’t wear a jacket even though it’s clearly 30 below outside. With average highs that would make your chilly neighbors seethe with envy, and the lowest precipitation of the year, Key West is your warm winter oasis. Buckle up, because we’re trading snowflakes for sand grains, and parkas for sunscreen as we embark on a detailed escapade to the Southernmost City. It’s all fun and sun (accented with a bit of laughter, of course).
Key West Weather Report: The Key to Wearing Shorts in Winter Months
It’s time for a little rundown on Key West’s February forecast, where the average high temperature of 76 degrees is practically begging you to swap out your thermals for a Hawaiian shirt. The lows, a cozy 66, still give you a gentle reminder that it’s not the hot and humid summer months quite yet. But let’s cut to the chase: This is the month with the least amount of rain, so you won’t need to dodge those pesky showers as you explore. And for those who are beach-bound (why wouldn’t you be?), the water temperatures ranging from 70 to 74 degrees are just dandy to dip your toes into, or maybe even a little more. Or plan to enjoy some of the other amazing water sports available in Key West. If the ocean isn’t your jam, a glass-bottom boat tour offers the perfect aquatic adventure, sans the wet feet, can offer a great time.
Oh, did I mention the sunshine? Yep, with an average of 22 sunny days, February is truly the champion of sunshine in Key West!
During February in Key West, you’re looking at around 11 hours of daylight to work with. That’s like having your very own spotlight for all of your favorite outdoor activities! Whether you’re hitting the beach, exploring the charming town, or just lazing around with a refreshing beverage in hand, you’ve got plenty of daylight to make it all happen. So plan to get out there and make the most of those daylight hours.
Check out these Glass Bottom Boat Tour Recommendations
February in Key West: Beating the Crowds with a Slice of Sunshine!
So my sun-seeking friends, there’s no better time to savor the soul-warming rays of Key West than in the month of February. It’s that sweet spot on the calendar when you can soak up all the laid-back charm without bumping elbows with high season and peak season swarms. This is the season when you feel like you’ve got the whole island to yourself, strolling down Duval Street, finding that perfect little hidden beach spot, or nabbing the best table at the local seafood shack while the rest of the country is buried under snowdrifts. And aren’t we all about those secret slices of paradise?
Worried about hurricane season? No need! Leave those dreaded hurricane warnings in the back of your mind, you can relax deeper and smile a bit brighter, knowing you’ve timed your escape to absolute perfection. February in Key West is a little slice of heaven, and who doesn’t love having their Key Lime Pie and eating it too?
Exploring Key West: A Pedestrian Paradise
Forget the car rentals at the Key West International Airport; Key West is meant to be seen on foot. The island’s walkability allows for a more intimate kind of exploration. Imagine strolling along Duval Street, the main drag, with live music as your soundtrack and the sound of the ocean just a sneeze away. Key West’s quirky shops, art galleries, and colorful street performers will keep you entertained for hours.
Grab our FREE list of Key West Happy Hours – Here
Other Activities: Finding Coral in Every Nook and Cranny
And when those pavement-strolling soles cry out for a reprieve, it’s time to book that adventure to Dry Tortugas National Park. This is definitely one of the top things visitors want to do.The ferry ride there is half the fun, and the park itself offers pristine beaches, snorkeling the coral reefs, and the historic Fort Jefferson—a citadel sitting in splendid isolation amidst the azure expanse a great place to just relax.
If the thought of Dry Tortugas whets your sea-faring appetite but the tickets are all snatched up, fear not. Key West, like a good book, has much to offer in terms of diverse chapters. Deep-sea fishing for the adventurously inclined, sunset sails for the romantically spirited, and guided culinary tours for those deciding fresh catch over angling it, are just the start. February is also packed with so many events you won’t be at a loss for anything to see or do.
And don’t forget Key West’s literary and creative heritage. Visit the home of Ernest Hemingway, where six-toed cats roam and the Nobel laureate’s writing room remains as if he just stepped out for a daiquiri. Or engage in some local shopping, supporting artisans at the Key West Artisan Market. Art, literature, and the bohemian spirit come alive in this small yet electric town.
Plan Your Tropical Treaty
During this time of year, crowds can be a bit unpredictable. But, fear not, overall we see fewer crowds, and sometimes, even good hotel prices. Be sure to check out our booking recommendations and resources here! Plus way too early to worry about those spring break and peak time crowds.
Embrace the island’s laid-back charm and free spirit, and trust me, you’ll set sail from Key West with your flag held high—figuratively, of course. When the rest of the world is draped in layers of winter woes, take the path less frosty and sink your toes into Key West’s warm sands. February might not be the busiest month in Key West, but what it lacks in crowds, it certainly makes up for in experiences that are uniquely and wonderfully Floridian. Book your tickets, plan your itineraries, and start practicing your pirate vernacular. In Key West, the treasure isn’t gold; it’s the spirit of adventure that waits for you to arrive, find your piece, and lose yourself in the beauty of this southernmost gem. Safe travels, mate.
Check out our list of What Not to Miss – Here
Here’s what’s happening in Key West in February:
William Hall: Bombshells – February 1 – 3, 2024
Bombshells is a one-woman show that introduces audiences to five distinct female characters, each brought to life through the talent of Erin McKenna, who skillfully embodies each character with nuance and authenticity. The play explores the diverse facets of modern womanhood, offering a compelling journey that is both humorous and poignant. Performances take place at 8 p.m. at Williams Hall, 729 Fleming St.
Caliente Cayo Hueso – Back in Time Fundraiser – February 2
Take a Trip Back to 1950s Cuba – Key West style – during this Back in Time Fundraiser for the Key West Art & Historical Society. Salsa your way down to the Key West Museum of Art & History at the Custom House at 281 Front St. in your best Cuban attire. Enjoy cocktail hour in the museum followed by an elevated Cuban dinner under the stars on Front Street. The Pilar Rum mojitos will be flowing at the full open bar while the Latin band Caribe Key West performs while you dance the night away. It will be a caliente evening you won’t want to miss.
Key West Theater: Tom Papa – February 3 – 4, 2024
As a veteran stand-up comedian, Tom Papa has found success in film, television and radio as well as on the live stage. He brings his live comedy show to Key West Theater for two nights, Saturday and Sunday with showtimes at 8 p.m. Tickets start at $45. 512 Eaton St.
Steampunk Pirate Ball – February 3
Get ready for a swashbuckling good time at the SteamPunk Pirate Ball on Sat. Feb. 3 from 6 to 9 p.m. at the Key West Woman’s Club, 319 Duval St. Tickets include a dinner buffet by the Royal Furniture Iron Chefs, live music by the Scallywagz, games, live and silent auctions and raffle giveaways. Costumes are encouraged. General admission $80, includes one drink; VIP $125 includes unlimited drinks. The event benefits May Sands Montessori charter School.
Artisan Market: Preserve Island Life Edition – February 4
Shop a curated outdoor market displaying delicious culinary creations, fine crafts, art and jewelry from talented Florida Keys makers. Listen to awesome local musicians, meet talented local authors and support the market’s featured cause. This week, the focus is on the City of Key West’s “Preserve Island Life” Campaign to to be more ecologically responsible and sustainable. As always, the market offers a full bar. The market is open 10 a.m to 2 p.m. every Sunday through April in Sonny McCoy Indigenous Park, 1881 White St.
USCGC Barbara Mabrity Ship Tours – February 6 -7, 2024
This Keeper-class coastal buoy tender of the United States Coast Guard will be open for public tours from 9 a.m. to 3 p.m. Tuesday and Wednesday at the docks at Truman Waterfront Park. The ship is named for the original nineteenth century Key West lighthouse keeper, Barbara Mabrity.
Key West Art & Historical Society: Distinguished Speaker Series – The History of Indian Key – February 8
Native Americans began visiting and living on Indian Key around A.D. 800, and were likely a submissive tribe to either the Tequesta or Calusa chiefdoms. In 1829 the island’s population was around 50 people, mostly transient fishermen, turtlers and wreckers. Jacob Housman of Key West bought Indian Key in 1831 and set out to build his own wrecking empire to compete with the monopoly in Key West. In 1840, Indian Key was attacked by a large party of Indians. Join speaker Barbara Edgar, president of the Matecumbe Historical Society, to learn about this along with more fascinating history of Indian Key, Thursday from 6 to 7 p.m. at Tropic Cinema, 416 Eaton St. Tickets $15.
The Studios of Key West: Anne McKee Fine Art Auction – February 9
This popular art auction features original paintings, sculpture, photography, fiber arts, ceramics, mixed media, jewelry pieces and more created by celebrated and renowned local masters to fresh new Florida Keys emerging artists. Proceeds are divided with half going directly to the artist, and the other half to the Anne McKee Artists Fund, supporting grants for projects by local artists in the visual, performance and literary arts. Doors open at 4:15 p.m. with the auction starting at 5 p.m. 533 Eaton St.
S/V Argo Navis: Doggie Day Sail – February 10
Well-behaved pups are welcome on the luxurious, 75-foot sailing vessel Argo Navis for the Doggie Day Sail from 11 a.m. to 1 p.m. with lunch included. Doggie Day Sails happen once a month all winter long. Cost is $100 per person, with or without a pup. A portion of each reservation is donated to the Florida Keys SPCA for animal rescue and care. The human lunch menu includes pork or brisket sliders, cucumber salad, pasta salad, and various other sides and desserts. The menu for canine passengers includes hot dogs, dog treats and barbeque burnt ends. There will be toys, treats and give-aways for all. Limited to 24 guests and 14 dogs. Board the boat at 0 Margaret Street in the Key West Historic Seaport.
Key West Artisan Market: Super Bowl Stock Up! – February 11
Shop a curated outdoor market displaying delicious culinary creations, fine crafts, art and jewelry from talented Florida Keys makers. Listen to awesome local musicians, meet talented local authors and support the market’s featured cause. This week, let’s get ready to rumble with the Super Bowl Stock-up Edition — perfect time to find everything you need for your game night or Super Bowl party. As always, the market offers a full bar. The market is open 10 a.m to 2 p.m. every Sunday through April in Sonny McCoy Indigenous Park, 1801 White St.
Coffee Butler Amphitheater: Willie Nelson – February 12
Willie Nelson and family return to Key West’s amphitheater for one night, Monday Feb. 12. Experience the magic as this living legend shares his music and stories from a remarkable career that has touched the hearts of millions. Tickets available online. Showtime 7 p.m. 21 Quay Rd.
The Studios of Key West: Rodney Crowell In Concert – February 13 – 14, 2024
Crowell came to prominence in Nashville in the 70s as a songwriter before establishing himself as a critically-acclaimed solo artist. He has 15 number-one hits to his credit and tracks recorded by the likes of Johnny Cash, Waylon Jennings, Emmylou Harris and Willy Nelson. NPR declared him the “elder statesman of the Americana scene.” Performances Tuesday at 7 p.m. in Helmerich Theater and Wednesday at 6 p.m. on the roof at Hugh’s View. Ticket prices vary, starting at $85. 533 Eaton St.
Wesley House Family Services Valentine’s Day Gala – February 14
Take your special someone to the annual Wesley House Gala Family Service’s Valentine’s Day Gala. The “Keys Formal” event features the island’s largest silent auction, open bar, live music and dancing, and an elegant dinner designed and prepared by Catered Affairs. Custom House Museum, 6 to 9:30 p.m. 281 Front Street.
Tennessee Williams Theatre: A String Quartet Plays Love Songs – February 14
Indulge your special someone in an enchanting evening as the string quartet weaves a musical tapestry of love songs across genres. From timeless classical favorites to cinematic melodies and your favorite love ballads, experience the universal language of love as the strings serenade you and your Valentine to the sweet sounds of Elvis Presley, Lady Gaga, Puccini and many more.
Presidential Families Weekend – February 15 – 19, 2024
A series of special events takes place over Presidents’ Day Weekend at the Harry S. Truman Little White House. On Thursday, Feb. 15, there is a kickoff “Happy Hour at Harry’s” cocktail and trivia event. Sat. Feb. 17, a panel of presidential descendants discusses “Political Maneuvering.” Other weekend highlights include Clifton Truman Daniel, the grandson of Harry S. Truman, performing the acclaimed stage production, “Give ‘Em Hell, Harry!” on Sunday and Monday, and a Sunday presentation by artist Tom Corbin, who sculpted the monumental Harry Truman bronze in the U.S. Capitol Rotunda. There will also be a traditional President’s Day cookout on Monday, Feb. 19 from 11:30 a.m. to 1:30 p.m. with picnic-style food available for purchase. Find more event information and ticket sales online. 111 Front Street, Key West.
Key West Art & Historical Society: Donovan Frankenreiter with Goodnight, Texas – February 15
Professional surfer turned singer/songrwriter Donavan Frankenreiter performs with Goodnight, Texas as his backing band in a concert under the stars on the grounds of historic Fort East Martello, 3501 S. Roosevelt Blvd., Feb. 15 from 6 to 10 p.m. Concertgoers are encouraged to bring chairs and blankets for the backyard casual setup that is to include food vendors and a cash bar. Tickets $25.
Tennessee Williams Theatre: Drum Tao – February 16
Drum Tao combines the unique sounds of Japanese Taiko drums with flute, harp and guitar, along with energizing choreography, vibrant sets and contemporary costuming, to create a large-scale performance experience that captivates audiences’ eyes and ears. Tickets $35 to $145. Showtime 8 p.m. 5901 College Rd.
Key West Home Tours – February 16 – 17, 2024
The Old Island Restoration Foundation’s Key West Home Tours are among America’s oldest and longest-running, dating from 1960. This 64th series features self-guided tours of several Key West homes and gardens. Home Tour tickets provide entry to 5 homes at your self-guided pace, between 1-4 p.m. during the Friday-Saturday tour. $55 per person. Addresses of featured homes are to be provided when tickets are purchased.
FKSPCA 5th Annual Pup Crawl – February 17
People and their pups are invited to register from 12 to 1 p.m. at one of two locations — Hank’s Hair of the Dog Salon at 409 Caroline St. or Tattoos & Scars at 512 Green St. — then at 1 p.m. stroll to all the participating bars in any order from 1 to 5 p.m.. The other locations are General Horseplay, Island Dogs Bar, Retro Room and Shots and Giggles. There will be a best trick contest at 2 p.m. at General Horseplay and a 4 p.m. a costume contest at Tattoo & Scars with lots of fun activities along the pup crawl including toys, treats, one drink at each b for humans, and more. There will be a dogs-only hydration station at Rick’s bar. Proceeds support Florida Keys SPCA.
Fringe Theater: Key West characters – True Stories – February 22 – 23, 2024
An evening of short plays, monologues and musical tributes that celebrate Key West. True stories include portrayals of Mrs. Ellen Sanchez, Bette Page, Sushi, Fats Navarro, Frank Merlo and more. Tickets $35. Doors at 6:30, seating is first-come, first seated for this special, community-focused program at Williams Hall, 729 Fleming St.
Key West Garden Club: Garden Tours – February 23 – 24, 2024
Nature lovers can tour the lush and verdant gardens surrounding four private Key West homes Friday and Saturday, Feb. 23-24, from 10 a.m. to 3 p.m. both days, during the once-a-year tours presented by the Key West Garden Club. All the tours this year are within easy walking distance of each other on VonPhister St. in the Casa Marina area. Participants can also explore the West Martello Gardens at club’s headquarters at 1100 Atlantic Blvd. Tickets may be purchased online, at the Garden Club or at two of the private garden locations on tour days.
Key West Theater: Best of Key West Songwriter Festival Series – February 23
The Best of Key West Songwriters Festival Series at Key West Theater presents Wendell Mobley & Lee Thomas Miller on Friday, Feb. 23. Both are top Nashville songwriters with songs you’ll instantly recognize that have been recorded by famous artists including Kenny Chesney, Chris Stapleton, Tim McGraw, Keith Urban and many others. Doors open at 7; show starts at 8 p.m. Tickets start at $45.
Key West Art & Craft Festival – February 24 – 25, 2024
The Key West Craft Show and Old Island Days Art Festival are now combined to create the Key West Art and Craft Festival. This new event includes artist demonstrations, a patron comfort station with valet package check, upscale food trucks, plenty of seating, and fun events and activities for children. The location for the combined show is along the Quay at Truman Waterfront Park, 100 Southard Street.
Tennessee Williams Theatre: Mike Super, Illusionist – February 24
Through spectacular illusions and his down-to-earth style and personality, Mike Super has pioneered a new form of magic that transcends the “trick.” He is the winner of NBC’s TV show “Phenomenon” and was a top finalist on “America’s Got Talent.” Tickets $35 to $145. Showtime 8 p.m. 5901 College Rd.
Schooner Wharf Bar: Wrecker’s Cup Race – February 25
The second of the 39th annual Wrecker’s Cup Race Series to Sand Key kicks off Sunday at 1 p.m. The all-in-fun race series recalls the tradition of the wreckers from Key West in the 1800s. All sailing vessels, local sailors and visiting yachtsmen are welcome to join the regatta. Spectators can view from Schooner Wharf and the Historic Seaport. After the races, first, second and third place will be awarded to the best time in each division, with trophies, a bottle of Pusser’s rum, Schooner Wharf Bar tabs and wrecker T-shirts as prizes. Future races are to be held Feb. 25, March 31 and April 28. Find Schooner Wharf Bar at 202 William St.
Tennessee Williams Theatre: Bobby in the Lobby – February 25 -26, 2024
After a four year hiatus, Bobby Nesbitt brings back his acclaimed series “Bobby in the Lobby” to the cabaret, celebrating one of the greatest songwriters of the 20th century, the brilliant Cole Porter. Joining Bobby will be Key West singer Carmen Rodriguez, and from New York, Susan Powell and Richard White. White is renowned for being the voice of Gaston in Disney’s Beauty and the Beast. Appearing Sunday and Monday nights at 8 p.m. Tickets $85 to $105. 5901 College Rd.
