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Fabulous February Events in Key West 2024

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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. Join us for Key West’s First ever Key Western Fest

More than 20 of the best classic country bands bring heir massive hits to the Southernmost City in the U.S. for five days of unforgettable songs, sun & sand! Take in the warm sunshine and tunes during the day at the island’s iconic bars, snag a bite from one of the renowned restaurants, leave your troubles on land during a live-music sail on a comfy catamaran, and then be ready to sing your heart out under the stars at night at The Truman Waterfront Amphitheater! Kick off party starts January 31st. Check out the lineup and purchase tickets here!

2. Enjoy a Stunning Sunset Sail

Enjoy an unforgettable evening aboard the SV Argo Navis, the only luxury catamaran sailing yacht in Key West, for 2 hours of craft food and drink pairings as the sun sets where the Atlantic Ocean meets the Gulf of Mexico. Your sail through the enchanting changing tropical colors of the sky and water includes a selection of craft beers and cocktails, fine wines, six rounds of charcuterie style passed appetizers and bean-to-bar chocolates chosen by the crew with suggestions from their sommelier. They don’t play any music and never overcrowd the boat so there’s a seat for everyone to enjoy space to stretch out and relax while experiencing the tranquility of a wind driven vessel. A sunset on the water is the original nightly show, and they’ve got the best front row seats. Purchase tickets here!

3. Daydream About Living On The Island

Best Activities in Key West

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 17 & 18

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

Top Things to Do Key West

Eat and drink like a local on the Southernmost Food Tasting and Cultural Walking 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 key lime pie on the island!

5. Stock up at the Farmers Market

Top Things to Do Key West February

Photo // Florida Weekly Key West

Every Thursday from 2 pm – 7 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.


6. Key West Artisan Market

The beloved Key West Artisan Market  will take place every other Sunday from 10 am to 2 pm at Clarence H. Higgs Memorial Beach, Key West. Guests will enjoy bloody mary’s & mimosas along with a full bar from Great Events CateringIslamorada Coffee Roasters, smoothies, natural juices and cut fruit, plus multiple food stalls offering eat-here or take-away. Guests will shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers and stock a pantry and fridge with fresh produce, artisan cheeses from The Cheese Lovers, local seafood from Mundy The Pirate Seafood, honey, pickles, pastries, cigars, soaps and so much more. Don’t forget, its BYOB (bring your own bag!)


7. Key West Master Chef’s Classic


Experience the culinary delight that is The Annual Master Chefs Classic©. Held at the Opal Key Resort and Marina Pier at 245 Front St, this culinary competition and tasting benefits the Monroe Association for ReMARCable Citizens (MARC provides life services for developmentally disabled adults in the Florida Keys). This event has become the premier food event of the Key West season. Some of the island’s best restaurants compete in appetizer, entrée and dessert categories providing an amazing array of incredible food for the lucky 450 people attending. Awards are given in each category by judges and people’s choice ballots. Check out the website here!


8. Old Island Days Art Festival


Take a stroll through the quaint tree lined streets of Old Town Key West during our 58th Annual Old Island Days Art Festival. Featuring nearly 100 carefully selected artists from far and wide, their fine arts and crafts will be showcased from the Truman Annex Residential Community all the way to the Truman Waterfront Park. Art aficionados will be delighted with all of the original artworks available in this nationally recognized open air show. Set up for the show is Saturday morning at 6 AM and the show will be open to the public from 10 AM to 5 PM both Saturday February 25 and Sunday February 26.


9. Sunday Night Jazz at The Gardens Hotel

The cooler weather in Key West means the return one of our favorite Sunday evening pastimes at one of Key West’s most beautiful hidden gems, The Gardens Hotel. This iconic hotel has been named Prettiest Hotel in Key West by the New York Times and is one of Conde Naste’s 100 Best Hotels in the World. As you enter the grounds, the smooth sound of live jazz leads you into a botanical paradise. The bar serves delicious cocktails and you can peruse the hand selected wines from all over the world within their state of the art self-serve D’vine Wine Bar. Then sit back and relax and let the music transport you to another time. Every Sunday night from 5-7:30.