Old Island Days Art Festival
The Old Island Days Art Festival (now officially renamed the Key West Art & Craft Festival) celebrates its 61st anniversary in 2026. This prestigious, juried outdoor show is a cornerstone of the island’s winter season, transforming the waterfront into a sprawling gallery for some of the country’s finest artists and craftspeople.
Festival Dates: February 21 – February 22, 2026
The festival runs from 10:00 AM to 5:00 PM on both Saturday and Sunday. It is a free, open-air event that invites both serious collectors and casual browsers to enjoy the creative energy of the island.
Location: The Quay at Truman Waterfront Park
Traditionally held on Whitehead and Caroline Streets, the festival has moved to the Truman Waterfront Park. This newer location offers:
Waterfront Views: Booths are lined up along the quay with the Gulf of Mexico as a backdrop.
More Space: The park allows for wider aisles and a more relaxed walking experience compared to the narrow historic streets.
Accessibility: Ample parking for patrons and a splash pad/playground nearby, making it a family-friendly choice.
What to Expect
The Talent: As a juried show, only about 100 artists are selected to exhibit. You will see high-end works in oil, watercolor, and acrylic, alongside professional photography, sculpture, and ceramics.
Fine Crafts: Expect more than just paintings—the “craft” portion of the show features unique jewelry, hand-woven fiber art, glasswork, and functional wood pieces.
Island Inspiration: Many artists specialize in “tropical” aesthetics, featuring local flora, fauna, and the iconic pastel architecture of Key West.
The “Oldest Gallery”: The event is hosted by the Key West Art Center, the island’s oldest art gallery (founded in 1960). It remains a non-profit community effort to support local artistry.
Pro-Tips for 2026
The February “Double-Header”: If you visit mid-month, you can catch two of the island’s best festivals back-to-back. The Florida Keys Seafood Festival (Feb 14–15) usually happens just one weekend before the Art Festival at the same location.
Meet the Artists: One of the best parts of this show is that the artists are required to be present at their booths. It’s a great opportunity to ask about their techniques or the stories behind their work.
Bike Over: While there is parking at Truman Waterfront, the easiest way to arrive is by bicycle. There are plenty of bike racks, and you’ll avoid the traffic congestion of Old Town.
Stay for Sunset: Since you’re already at the Truman Waterfront, walk a few blocks over to Mallory Square or stay at the park’s pier to watch the sunset once the festival booths close at 5:00 PM.
