34th Annual Florida Keys Island Fest
Each spring, the Florida Keys Island Fest brings two days of vibrant community celebration to Founders Park in Islamorada. Organized by the Islamorada Chamber of Commerce as a signature fundraiser, this beloved festival showcases juried fine art, live music, local cuisine, family activities, vintage cars, and waterfront fun.
With over 100 artists and crafters presenting works ranging from paintings and sculptures to jewelry and driftwood carvings, the Arts & Crafts Show is a highlight for collectors and art enthusiasts alike. Visitors can also sample diverse culinary offerings—from fresh seafood and barbecue to Mediterranean and Mexican fare—while enjoying annual favorites like the Smoked Fish Dip Contest with people’s choice voting.
Car lovers will appreciate the All-American Road Vintage Cruisers Car Show, where antique cars, custom rods, motorcycles, and rat rods take center stage with awards like “Coolest Cruiser” and “People’s Choice.” For a playful twist, participants can join the whimsical “What Floats Your Boat?” homemade boat race (and a “Floaties” race for kids 10 and under), with trophies such as the Lucky Ducky Admiral Award and Krazy Krewe Award.
Guests of all ages will find something to love—kids can paint a life-sized dolphin sculpture, build sand creations, take part in hula hoop contests, or fly kites along the beach. Meanwhile, multiple musical acts spanning country, blues, reggae, jazz, and rock perform on the main stage right by the water.
Admission is free, with an optional parking donation, and the event runs rain or shine from 10 a.m. to 5 p.m. both days. Organizers encourage attendees to “Keep the Scene Green” by bringing reusable drink containers and enjoying lawn chairs or blankets for comfort.
Whether you’re an art lover, foodie, vintage car fan, or family looking for an unforgettable weekend, the Florida Keys Island Fest captures the warm spirit, creativity, and coastal charm of Islamorada—making it one of the region’s must-attend spring festivals.
