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10 Fabulous February Events in Key West 2021


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

Photo //

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. Be a Know-it-All at Trivia Night!

Grab your friends, colleagues and KWAHS members and join our non-profit’s amazing night of trivia, drinks, snacks and fun. There will be 5 categories – Animals, Literature, Corporate Logos, Who Said It?, and U.S. States.  Great prizes for the 1st, 2nd and 3rd place teams! Off the Hook Grill offers Happy Hour from 4pm-6pm, so come thirsty and hungry! $5 per person


3. Jam out at the 3rd 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. Jan 28-Feb 1st


4. See Legendary Musical Acts

Kool and the Gang, The Village People, and Willie Nelson are all in Key West this month, so don’t miss you chance to see them and sing along to the songs that you grew up with! Various days and times but all happening at the Key West amphitheater!

5. 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.


6. 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. Feb 15 & 16


7. 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!

8. Luau on the Beach!

Please join us for Reef Relief’s 2nd annual Luau Party at Lagerheads Beach Bar and Grill. Join us for a night of tropical food and drink specials, live music by the one and only Tony Baltimore, a silent auction, and luau games. All proceeds from the silent auction benefit Reef Relief. Please come dressed in your best luau attire and bring the whole family!


9. Stock up at the Farmers Market

Photo // Florida Weekly Key West

Every Thursday from 10 am to 2 pm the Truman Waterfront will offer fresh produce grown in Homestead, gorgeous orchids & native plants, artisan selection of meats and cheeses, pickles, honey, nuts & dried fruits, natural soaps and so much more. You’ll find Key West crafts, gifts and the perfect souvenir to take home. There’s lots of parking, bike racks, or take the FREE Duval Loop which conveniently stops close to the market. We hope to see you as we GROW LOCAL at your all new Key West Farmers Market, Thursdays at the Truman Waterfront.


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.