M-F: 9-5 / Sat: 9-4 / Sun: 9-3 Mon-Fri: 9am-5pm / Sat: 9am-4pm / Sun: 9am-3pm

Official Islamorada Visitor Information from a local point-of-view

Call an Islamorada Vacation Specialist! 800-FAB-KEYS 305-664-4503

Purple sky sunset through palm fronds

Island Fest

Islamorada 30th Annual Island Fest
Saturday & Sunday, April 2 & 3, 2022
Founders Park, Islamorada

Island Fest returns to Islamorada on April 2 & 3, 2022 featuring a juried art show, live music, great food, classic cars and much more. The annual Islamorada Chamber of Commerce fundraiser, now in its 30th year, will take place from 10 a.m. to 7 p.m. on Saturday and 10 a.m. to 5 p.m. on Sunday at Founders Park, mile marker 87 bayside.

Sand castle

The Plantation Yacht Harbor Arts and Crafts Show will feature approximately 100 artists whose works include everything from paintings and sculptures to jewelry, fine crafts, and even driftwood carvings. Recognized as this year’s poster artist is painter, Derek DeYoung, whose work Tarpon at Play captures the joyful nature of this powerful fish. Says his wife and partner, Janelle, “As a boy Derek dreamt of one day living in the Keys. Today, he spends the Winter months in Big Pine Key, and has done so for the last 8 years. Beyond just living the island life, Derek worked extremely hard to master the art of catching flats gamefish on a fly, as well capturing them in his unique and captivating style in acrylic paint on his canvases. To be named poster artist for Island Fest has meant the world to Derek, as he truly considers the Florida Keys his home, and is so honored to represent his fellow Keys artists this year for Island Fest.”

Click Here for Arts and Crafts Show additional information

Click here for an Artist Brochure and Application

Great food is always a mainstay during both days of Island Fest. The culmination of local culinary greatness will come Sunday at noon when the Taste of Islamorada competition brings out top local restaurants to show off their most mouthwatering dishes. Attendees will get to cast their ballot for the coveted People’s Choice Award. The awards ceremony will take place on the stage at 4 p.m. on Sunday.


All-American Road Vintage Cruisers Car Show

Back at Island Fest this year for car enthusiasts is the All-American Road Vintage Cruisers Car Show, featuring antique cars, trucks, motorcycles and rat rods. The show will be visible from US-1, Florida’s only official “All American Road,” encouraging passersbys with an interest in antique and unique cars to stop for a look. Awards will be presented for Coolest Cruiser, Raddest Rod, KeyZ Rider, Longest Haul, Big Kahuna, Funkiest Foreign, Best of Show, and People’s Choice. New entrants are always encouraged.

An array of popular musical acts appealing to music lovers of all genres will perform throughout festival. Acts will range from country and rock to blues and reggae. No matter what your musical taste, there is something for everybody on the main stage at Island Fest.

Click here for more entertainment information


Paint the dolphinPaint the dolphin

Island Fest offers fun for the whole family! Children and child-like adults can help paint a life-sized dolphin statue, build sand castles, and compete in hula hoop contests with kites flying high in the sky. In addition, teams will venture to the beach on Saturday, where they will compete to construct the best sand sculpture inspired by this year’s theme of “Pirates, Ships and Treasure Chests”.


What Floats Your Boat

Also on the show’s first day is the wacky and wonderful “What Floats Your Boat?” homemade boat race. Participants will create a “boat” to enter in the race, which will begin at 1 p.m. Saturday. There is no entry fee and the Chamber of Commerce is currently seeking entries. Winners will be declared for the Yachtiest Award, Thriftiest Award, Anchor Award, Krazy Krewe Award and Sink and Swim Award. The big winner will be presented with the Lucky Ducky Admiral Award.

Back again this year by popular demand is kids’ division of the race – “What Floaties Your Boat?” for participants 11 and under. Teams can enter with their favorite swimming pool float. Prizes include but are not limited to Duckiest Award, the Super Star and the Scallywag.

reusable drink containers

Admission to Island Fest is free and on-site parking is available for a $5 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.