Can't-Miss Events
Find the Ancient City's latest and greatest events.
Throughout the year, St. Augustine hosts unforgettable festivals, live music, and cultural celebrations. Whether it’s a nationally recognized music festival, a holiday festivity, or an authentic reenactment, there's always something BIG happening in this tiny town. From art exhibits and live theater to historical events and culinary creations, our can't-miss events feature the best of the nation’s oldest city.
Friday
May 1
May 1
A Classic Theatre: Rounding Third
Friday, May 1 - Sunday, May 10, 2026 | See Times Below
This two-man play portrays two Little League coaches and their season.
Saturday
May 2
May 2
Baroque Quartet
Saturday, May 2, 2026 | 2:00 p.m. to 3:00 p.m.
Four classical musicians perform music by Baroque Masters.
Saturday
May 2
May 2
St. Augustine Orchestra: Afternoon Tea
Saturday, May 2, 2026 | 4:00 p.m. - 6:00 p.m.
Listen to chamber music and enjoy an elegant sweet and savory tea.
Sunday
May 3
May 3
Lisa Lockhart & Friends: "Sposi Cantanti"
Sunday, May 3, 2026 | 7:30 to 9:00 p.m.
Four vocalists + two pairs of spouses = one program about love and marriage.
Monday
May 4
May 4
Chamber Music Series: John Daugherty
Monday, May 4, 2026 | 12:00 p.m. - 1:00 p.m.
Romanza presents John Daugherty, opera singer, with Keith Teepen, pianist.
Monday
May 4
May 4
Romanza Presents Vivace!
Monday, May 4, 2026 | 6:45 p.m. to 8:00 p.m.
Three local vocalists, harmonize and swing with the sounds of the 40s and 50s.
Tuesday
May 5
May 5
Jonathan Dotson and the SJCCA Guitar Ensemble
Tuesday, May 5, 2026 | 7:30 p.m. to 8:30 p.m.
Guitarist Dr. Jonathan Dotson, and the high school classical guitar ensemble perform.
Wednesday
May 6
May 6
St. Augustine History Fest Tours, 2026
Wednesday, May 6 - Sunday, May 10, 2026 | Times and Locations Vary
These historic properties offer free tours during one week in May.
Wednesday
May 6
May 6
St. Augustine History Fest, 2026
Wednesday, May 6 - Sunday, May 10, 2026 | Times and Locations Vary
St. Augustine hosts an annual history festival in May of 2026.
Wednesday
May 6
May 6
Chamber Music Series: Sunny (Kyeong Seon) Choi
Wednesday, May 6, 2026 | 12:00 p.m. - 1:00 p.m.
Romanza presents music from Korea in this special chamber music event.
Wednesday
May 6
May 6
St. Augustine Food + Wine Festival—2026
Wednesday, May 6 - Saturday, May 9, 2026 | Times and Locations Vary
Great food, wine, and more at two locations over three days.
Wednesday
May 6
May 6
Romanza: Joyous Music with St. Paul AME Church
Wedensday, May 6, 2026 | 7:30 p.m. to 9:00 p.m.
Enjoy an evening of music featuring the church choir and special guests.
Thursday
May 7
May 7
Florida Storytelling Troupe with Florida Stories
Thursday, May 7, 2026 | 2:00 to 3:00 p.m.
Two who received the Ambasador of Storytelling Award relate old and new Florida tales.
Thursday
May 7
May 7
Kim Bradley, Author—Wine and Cheese Event
Thursday, May 7, 2026 | 3:00 p.m. - 4:00 p.m.
Romanza hosts a discussion on research and the art of writing historical fiction.
Friday
May 8
May 8
Drake's Raid Reenactment
Saturday, May 8, 2026 | 7:00 p.m. - 9:00 p.m.
Members of Florida Historic Militia reenact Sir Francis Drake's siege of San Agustin in 1586.
Friday
May 8
May 8
St. Augustine Concert Band Season Finale
Friday, May 8, 2026 | 7:30 p.m. - 9:00 p.m.
The Romanza Festivale presents the band's last concert of the season.
Saturday
May 9
May 9
Sunflower & Tomato Soirée
Saturday, May 9, 2026 | 9:00 a.m. - 4:00 p.m.
Visit a thriving family farm, purchase produce, and take part in the festivities.
Saturday
May 9
May 9
Romanza: Flo-Arts Students with Broadway and More!
Saturday, May 9, 2026 | 4:00 p.m. - 5:00 p.m.
Florida School of the Arts students perform music from Broadway for Romanza.
Saturday
May 9
May 9
Romanza: St. Augustine Community Chorus
Saturday, May 9, 2026 | 7:00 p.m. to 9:00 p.m.
The St. Augustine Community Chorus offer a program titled "The Way to Peace."
Sunday
May 10
May 10
Romanza: Akia Uwanda and Jerome Kyles
Sunday, May 10, 2026 | 7:30 p.m. – 9:00 p.m.
An internationally loved jazz and soul vocalist performs with a singer/keyboardist.
Friday
May 15
May 15
St. Augustine Ballet: "Rapunzel"
Friday, May 15 & Saturday, May 16, 2026 | Times Vary
Experience the tale of a trapped girl in a tower awaiting freedom and love.
Friday
May 15
May 15
Romanza Festivale: The Echo Piano Duo
Friday, May 15, 2026 | 7:30 p.m. to 9:00 p.m.
These two pianists have performed in the United States, Germany, and China.
Friday
May 15
May 15
Romanza: St. Augustine Orchestra Spring Concert
Friday, May 15, 2026 | 7:30 p.m. - 9:00 p.m.
For their final concert of the season, the orchestra brings Broadway to town.
Saturday
May 16
May 16
Gamble Rogers Concert Series: Walter Parks
Saturday, May 16, 2026 | 7:00 p.m. - 10:00 p.m.
This virtouso guitarist performed with Richie Havens, and is an expert on folk music.
Saturday
May 16
May 16
A Gamble Rogers Concert: Pat Bergeson & Bruce Forman
Select Saturdays Oct. 18, 2025 - Jun. 20, 2026 | 7:00 p.m. - 10:00 p.m.
St. Johns County Cultural Council presents this concert series.
Saturday
May 16
May 16
Romanza: The Gainesville Brass Quintet
Saturday, May 16, 2026 | 7:30 p.m. to 9:00 p.m.
Catch this brass concert featuring five brass musicians and organist, Thomas Rodgers.
Sunday
May 17
May 17
Romanza Festivale: Big Orange Chorus
Sunday, May 17, 2026 | 7:30 p.m. to 9:00 p.m.
A large chorus of Barbershop Singers, brings a big sound to four-part harmonies.
Friday
May 22
May 22
Blue Crab Festival 2026
Friday, May 22 - Sunday, May 24, 2026 | Times Vary
Eat delicious seafood with the company of live music and family activities.
Saturday
May 30
May 30
PechaKucha: Slow Down
Saturday, May 30, 2026 | 6:00 p.m. - 9:30 p.m.
Taking your time, or not—come see the diverse stories based on the topic.
Saturday
May 30
May 30
Ancient City Limits: Amy Hendrickson & John Dickie IV
Saturday, May 30, 2026 | 7:00 p.m. to 9:30 p.m.
Ancient City Limits presents singer/songwriters Amy Hendrickson and John Dickie IV.
Editor's Note: We encourage you to verify event times and details with the organizers, as they may change.
