Living Like a Local: Key West’s Best Spring Events and Festivals

Springtime in Key West is nothing short of magical! As the island bursts to life with sunshine, cool breezes, and vibrant energy, it also becomes the perfect backdrop for some of the best festivals and events of the year. Whether you’re a long-time local or planning a visit, April 2025 is packed with exciting happenings you won’t want to miss.

As a local Key West realtors, we love sharing insider tips about the island's most anticipated events.

Here’s your guide to Key West's best spring events and festivals in April 2025!

Key West Historic Days Celebration (April 3–6, 2025)

Step back in time at the Key West Woman’s Club as they celebrate their 110th anniversary at the Hellings Curry Museum (319 Duval Street). This free four-day event features docent-led tours of historic sites, live performances by local musicians like the Key West High School Steel Drum Band, and fascinating talks about our island's deep-rooted history. It’s the perfect way to experience Key West’s cultural heritage!

A Swinging Night with the Heart Starters (April 12, 2025)

Looking for a unique night out? The Harry S. Truman Little White House (111 Front St.) is hosting an unforgettable evening of live music from the 1940s and 1950s. Enjoy a cocktail reception starting at 5:00 PM, followed by a performance from the award-winning Key West Jazz Society tribute band, The Heart Starters. This event is a must for music lovers and history buffs alike!

Key West Sailfish Tournament

Fishing enthusiasts, get ready! The Key West Sailfish Tournament brings world-class anglers to our beautiful waters for a two-day competition. Whether you're participating or cheering from shore, this tournament is an exhilarating showcase of Key West’s legendary fishing scene.

More Key West Events in April 2025

While some events are still finalizing their dates, be sure to keep an eye out for other incredible happenings, including:

Key West Pride Celebrations: A week-long event featuring lively parades, dance parties, historical tours, and fun-filled daytime sailing excursions.
Local Art & Food Festivals: Explore unique island art, delicious cuisine, and live entertainment at various locations throughout the month.

Plan Your Spring in Key West!

For the latest updates on these and other Key West spring events, check out the Key West Chamber of Commerce's event calendar.

And if you fall in love with the island (trust me, it happens to the best of us!), I’m here to help with all your Key West real estate needs.

Whether you’re looking to buy, sell, or just explore, let’s chat about finding your dream home in paradise!

Happy Spring, and see you at the festivals! 🌴