Top 10 Things to Do in Key West in February 2025: Festivals, Tours, and More
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. Eat Your Heart Out at the Florida Keys Seafood Festival
Fried Fish baskets, Grilled Spiny Lobster Platters, Stone Crab Claws with key lime mustard sauce, peel and eat Key West Pink Shrimp with cocktail sauce, Smoked Fish Dip with crackers, Creamy Lobster Bisque, Bahamian style Conch Chowder, Conch Ceviche, & Conch Fritters – have we gotten your attention yet?? This family-friendly event was created to showcase local seafood and the Keys’ commercial fishing industry by providing the freshest seafood available. Each year our fishermen and women are proud to offer the community a variety of seafood at reasonable prices. This years dates are February 15th & 16th.
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
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. Dates to be determined
4. Enjoy Tropical Weather (in Feb!) on a Walking Tour
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
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. 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 Catering, 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 Art & Craft Festival
Key West Craft Show and The Old Island Days Art Festival have been combined to become The Key West Art and Craft Festival. Featuring nearly 100 carefully selected artists from far and wide, their fine arts and crafts will be showcased along the beautiful Truman Waterfront Park. Art aficionados will be delighted with all of the original artworks available in this nationally recognized open air show. February 24 and Sunday February 25.
8. 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.