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10 Fabulous February Events in Key West 2020


Winter in Key West means outdoor activities. With average February temps at a brisk 76 degrees (sorry to rub it in), we’ve got no reason to stay indoors with our a/c on. February is peak high season here on the island, which means plenty of events to fill up your social calendar. We’ve compiled a list of our favorite things to do this month… And none of them involve snow.

1. Catch A Burlesque Show

Key West burlesque dancer taking it off on stage

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If you like a good look from the rear, head to the back door to see this season’s Key West Burlesque! Now at the Back Space inside of SideBar, 504 Angela Street, the new show excites two nights  a week (Fri & Sat). It’s sure to make naughty dreams come true. Ticket Prices are $35 VIP seating next to the stage; $25 High cocktail table and bar stool; $20 Standing room.  Get tickets here.


2. See the Gato Cigar Factory in a New Light!

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With the Grand Opening February 1st, The Gato Cigar Factory will feature “Visions of Cuba,” a Cuban artists’ exhibition, featuring contemporary artwork from over 40 prominent Cuban artists. The opening is set for 5:30 – 7:30PM at Gato Cigar Factory, 1100 Simonton St. with wine, music, and hors d’oeuvres and will be on display through May 3.


3. Jam out at the 2nd Annual Mile Zero Fest

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Mile 0 Fest Key West is a new music festival considered a “must see” in the burgeoning Red Dirt & Americana music scene. Take in big shows at Truman Waterfront Park Amphitheatre, a state-of-the-art facility located blocks off the hopping streets of Duval, or get into a stripped down acoustic set with your favorite band leader at one of the theaters or bars off Duval. Many activities and memorable experiences await.

4. Get Hungry for the 4th Key West Food Truck Festival

Photo // KWAHS

Don’t need an excuse to spend a Saturday lounging, munching, and grooving to good beats? Well, we have on anyways! From 12-7 p.m. on February 9th, the Key West Art & Historical Society event will transform the Fort East Martello parade grounds into a family-friendly musical feast with the tasty delights of Key West’s top-notch food trucks and the grooving tunes of local and international acts. Key West Food Truck Fest is set to feature Triano’s Taco food truck,  Irie Island Eats, Flamingo Street, The Raw Machine, Jimmy Sno Concessions, The Pincho Barge, Tarpon River Brewing, Great Events Catering, Key West Glass Works, and more.  Tickets $5 at the door


5. Be a Dancing Queen at the ABBA Tribute Show

Photo // Infinity Music Hall

Witness the most authentic ABBA show ever, delivered in exact replicas of ABBA’s famous staging clothes exclusively approved by ABBA’s clothing designer. Arrival from Sweden performs together with some of the finest symphony orchestras in the world and also with ABBA original musicians. Feb. 11th. More info here.

6. Enjoy a Sexy Sunset Sail

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Looking for a romantic Valentine’s Date that will stun? Treat your sweetheart to an unforgettable evening sailing the blue waters of Key West at sundown. As it’s a special night, America 2.0 will treat you to a delicious pairing menu that is sure to entice, consisting of hors d’ oeuvres expertly paired with champagnes and sparkling wines from around the world! More info here.


7. Treat your pup to the 1st Annual Pup Crawl!

The Green Room proudly presents the 1st Annual Pup Crawl sponsored by Sea Dog Brewing Co!  You and your fur babies will sniff your way from bar to bar and engage in various pet-friendly activities at each location alongside fellow animal lovers. Treat your pup to complimentary toys, take photos, create artwork and win prizes. Don’t have a dog? The SPCA will be showcasing pups available for adoption. There’s even a puppy pool pawty! This dog-gone day is set for Saturday February 16, benefitting the Florida Keys SPCA. Fetch your tickets now at

8. Daydream About Living On The Island

Picturesque key west cottage open for tours

Photo: Key West Properties

See what island life really feels like on the annual house tours. This might be our absolute favorite thing to do during this time of the year. We’re architecturally obsessed.  The tour is leisurely and you go at your own pace. There are five houses on each tour, with a map provided of where each one is in old town. What seems like a small, Conch house on the outside, will blow your mind once you step inside.


9. Enjoy Tropical Weather (in Feb!) on a Walking Tour

Tour Rum Runners from The Speakeasy Inn and Rum Bar Key West

Eat and drink like a local on the Southernmost Food Tour in old town. 75 degrees and sunny makes this walking tour a breeze, but learning about the culture through our cuisine is the standout of the tour. And trust us, we have the best rum runners on the island!


10. Stroll the 54th Annual Old Island Days Art Festival

Photo // KWAHS

The 54th Annual Old Island Days Art Festival features juried artists of oil paintings, watercolors, sculpture, photography and other offerings by more than 100 artists from around the United States and beyond. The event takes place on lower Whitehead Street in historic Old Town.



Photo // Key West Full Moon Party

If you happen to be here during the full moon (Feb. 19th), hit the beach for a fun, entertaining experience during the bewitching hours! Yoga, music, dancing, food and drinks available. Bring your hula hoop and an open mind and mingle with locals and tourists alike on our sandy shores. $12 suggested donation gets you a welcome cocktail and helps support the sponsors who donate to make the event fabulous every full moon. More deets on their FB page.