ANNUAL ISLAND FEST BRINGS BOATS, FLOATS, MUSIC & MORE TO FOUNDERS PARK APRIL 5-6

a sand castle sitting on top of a sandy beach
A sculpted sand castle along the beach.

The Islamorada Chamber of Commerce’s 33rd Annual Island Fest will take place on Saturday and Sunday, April 5-6, from 10 a.m. to 5 p.m. at Founders Park, MM 87, bayside. 

The event will feature a juried art show, live music, food, classic cars, homemade boat races, the Keys Kids Business Fair and more.

The Arts & Crafts Show will spotlight a diverse range of local artists, including painters, sculptors, jewelers and creators of fine crafts and green market items. This year’s poster artist is local artist Jane Wood of Big Pine Key.

Returning for another year is the All-American Road Vintage Cruisers Car Show, which will feature a collection of antique cars, featuring different makes and models plus classic and custom designs. 

The music lineup covers everything from tropical Americana and Southern rock to classic hits and crowd favorites from the main stage set on the Founders Park beach.

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, “Octopus and Jellyfish Jubilee.”

The first day of the event will highlight the “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 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 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 floaties to the finish line for prizes like the Duckiest Award, Super Star and Scallywag.


After a long hiatus, the Keys Kids Business Fair is back. This event allows young entrepreneurs to showcase their creativity and business skills, offering a platform for kids to sell crafts, treats and unique products. Young vendors will have the chance to engage with customers, gain 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 a reusable drink container to reduce plastic use during the event.  Events will take place rain or shine. Lawn chairs and blankets are welcome. More information is available from the Islamorada Chamber of Commerce at 305-664-4503.