34th Annual Florida Keys Island Fest

Event Description

34th Annual Island Fest Set for March 28 & 29, 2026

The Islamorada Chamber of Commerce is excited to announce the 34th Annual Island Fest, taking place on Saturday and Sunday, March 28 & 29, from 10 a.m. to 5 p.m. at Founders Park (mile marker 87 bayside). This lively event will feature a juried art show, live music, delicious food, classic cars, homemade boat races, the Keys Kids Business Fair, and much more!

The Arts & Crafts Show will spotlight a diverse range of regional artists, including painters, sculptors, jewelers, and creators of fine crafts and green market items. This year’s poster artist is talented local artist Jessica Ann of Islamorada

Returning for another year is the All-American Road Vintage Cruisers Car Show, which will feature an impressive collection of antique cars, featuring all makes and models plus classic and custom designs. With a prime location visible from US-1, the car show is sure to draw attention from car enthusiasts and curious onlookers alike.

Whether you're into beachy island rhythms, gritty blues, or high-energy country, Island Fest brings it all. Our diverse music lineup covers everything from Reggae and Southern Rock to classic hits and crowd favorites—with music filling the air from the main stage set on the sandy Founders Park beach.

Island Fest is fun for all ages! Kids (and kids at heart) can join in painting a life-sized dolphin statue, participate in hula hoop contests, or watch giant kites soaring above. Saturday will also feature a sand sculpture competition, where teams will craft masterpieces inspired by this year’s theme, “Flamingos and Fairies.”
Also, the first day of the event will highlight the quirky and fun “What Floats Your Boat?” homemade boat race. Participants can enter by creating their own boat, with the race taking place on Saturday. Entry is free, and the Chamber of Commerce is currently seeking participants. The grand champion will be awarded the Lucky Ducky Admiral Award—a perpetual roaming trophy that is updated each year with the winning team’s name. Other teams can paddle away with playful rubber ducky awards like Most Spirited, FantaSEA, or Crowd Pleaser, celebrating creativity, spirit, and fun on the water.
Kids 10 and under can join the fun in the ‘What Floaties Your Boat?’ race, paddling their adorable floaties to the finish line for prizes like the Duckiest Award, Super Star, and Scallywag.

The Keys Kids Business Fair returns to Island Fest! This special event allows young entrepreneurs to showcase their creativity and business skills, offering a platform for kids to sell handmade crafts, delicious treats, and unique products. Young vendors will have the chance to engage with customers, gain valuable business experience, and compete for cash prizes.
Admission to Island Fest is free and on-site parking is available for a $10 donation. The Islamorada Chamber of Commerce encourages the public to “Keep the Scene Green” and bring your own reusable drink container to reduce plastic use during the event. Events will take place rain or shine. Plan to bring your own lawn chairs, and blankets for a comfortable, fun-filled day. For more information, call the Islamorada Chamber of Commerce at 305.664.4503.