February in the Florida Keys & Key West: Food, Culture & Life on the Water
From signature festivals to scenic adventures, February offers countless ways to turn a winter escape into a true island experience in Key West.
Food, history, and adventure shine across the Florida Keys & Key West in February 2026, as a lively lineup of events unfolds from Key Largo to Key West. Mild midwinter days and abundant sunshine set the stage for outdoor celebrations, culinary indulgences, and cultural experiences.
20th Annual Florida Keys Seafood Festival
February 14–15
The Florida Keys Seafood Festival is back and bigger than ever as it celebrates its 20th anniversary at Key West’s Truman Waterfront Park. Indulge in fresh, locally caught seafood while enjoying live music and shopping for island-inspired art. Sip on beer, wine, or frozen rum cocktails while soaking up the waterfront vibes. Tickets are reasonable, as the seafood is $10 for adults (kids under 12 are free) and includes a chance to win $250 worth of Florida Keys seafood shipped straight to your door. Best of all, every bite supports sustainable fisheries and youth scholarships in the Keys.
Conch Cuisine Celebration
February 27
Food history takes center stage at the Key West Museum of Art & History as the new Celebrating Conch Cuisine exhibit debuts with a free opening reception on February 27. Blending interactive displays, rare artifacts, and immersive multimedia storytelling, the exhibit traces how the Florida Keys’ signature flavors were shaped over time. On view through January 3, 2027, the exhibition was created in collaboration with local historians, chefs, and cultural experts and builds on the Smithsonian’s renowned Food History exhibitions. From Indigenous traditions and Afro-Caribbean roots to Cuban and Bahamian influences and maritime trade routes, visitors will discover the rich mix of cultures that seasoned the Keys’ cuisine.
Spanish Fly Music Festival
February 1
Live music takes the spotlight as the Spanish Fly Music Festival returns to Boondocks Grille & Draft House on Ramrod Key for its eighth year. Created in honor of legendary captain Jose Wejebe, this laid-back island celebration blends great tunes, waterfront vibes, and a deep love for life on the water. Come for the music, stay for the camaraderie. Learn more.
Sombrero Beach Run: Marathon
February 7–9
Runners of all fitness levels can take in this scenic race weekend along Marathon’s picturesque Sombrero Beach. Ocean views, a festive atmosphere, and post-race celebrations make this a favorite for active travelers. Learn more.
Tropical Luncheon & Garden Party: Key West
February 8
Step into Key West’s Old Town elegance at the Hellings Curry Museum, where island flavors, rich storytelling, and refined garden-party vibes come together for a one-of-a-kind cultural afternoon. Learn more.
Presidential Families Weekend: Key West
February 15–17
History comes to life at the Harry S. Truman Little White House as presidential descendants, including Amy Carter, James Carter IV, Josh Carter, Susan Ford Bales, and Clifton Truman Daniel, gather in Key West to share rare, personal stories from America’s most famous families. The weekend features an intimate meet-and-greet, a moderated conversation, a theatrical portrayal of Harry S. Truman, and a festive Presidents’ Day cookout. It’s the nation’s largest gathering of presidential descendants held over Presidents Day Weekend—set in one of America’s most iconic presidential retreats. Learn more.
Key West Art & Craft Festival: Key West
February 21–22
Art meets the waterfront as Truman Waterfront Park becomes an open-air playground for creativity. Local and regional artists bring their boldest, brightest work to Key West’s largest outdoor art show, inviting visitors to browse, mingle, and get inspired with ocean views as the backdrop. Come for the art…stay for the island vibes. Learn more.
