Things to Do This May in St. Augustine
This month, the city is full of life with vibrant festivals, cultural happenings, and outdoor fun that will make your visit truly memorable. Whether you’re diving into our rich history, savoring delicious local food, or catching live music under the stars, there’s plenty to explore.
Join the Fun with Local Events
FIRST FRIDAY ART WALK
Friday, May 2, 2025 | 5:00 p.m. – 9:00 p.m.
AS IF! THE ’90S FEST
Saturday, May 3, 2025 | 2:00 p.m. – 9:00 p.m.
ST. AUGUSTINE HISTORY FESTIVAL, 2025
Wednesday, May 7 – Sunday, May 11, 2025 | Times and Locations Vary
ST. AUGUSTINE FOOD + WINE FESTIVAL
Wednesday, May 7 – Sunday, May 11, 2025 | Times and Locations Vary
SUNFLOWER AND TOMATO FESTIVAL 2025
Saturday, May 10, 2025 | 9:00 a.m. – 5:00 p.m.
MICHAEL FRANTI & SPEARHEAD AT THE ST. AUGUSTINE AMPHITHEATRE
Thursday, May 15, 2025 | 6:30 p.m. – 10:00 p.m.
ST. AUGUSTINE BALLET: “RAPUNZEL”
Saturday, May 17, 2025 | 1:30 p.m. & 7:00 p.m.
DYLAN SCOTT AT THE ST. AUGUSTINE AMPHITHEATRE
Saturday, May 17, 2025 | 7:00 p.m. – 10:00 p.m.
HAUSER AT THE ST. AUGUSTINE AMPHITHEATRE
Sunday, May 18, 2025 | 8:00 p.m. – 10:00 p.m.
BLUE CRAB FESTIVAL 2025
Friday, May 23 – Sunday, May 25, 2025 | Times Vary
RICK SPRINGFIELD AT ST. AUGUSTINE AMPHITHEATRE
Thursday, May 29, 2025 | 6:30 p.m. – 10:00 p.m.
SAM BARBER AT THE ST AUGUSTINE AMPHITHEATRE
Friday, May 30, 2025 | 7:00 p.m. – 10:00 p.m.
