Tuesday
May 5
May 5
Romanza Festivale: Jonathan Dotson + SJCCA Guitar Ensemble
Tuesday, May 5, 2026 | 7:30 p.m. to 8:30 p.m.
Professor and students present a classical guitar concert.
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.
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
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
Romanza Festivale: Sunny (Kyeong Seon) Choi
Wednesday, May 6, 2026 | 12:00 p.m. - 1:00 p.m.
This special chamber music event features Korean culture.
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
Wednesday, May 6, 2026 | 7:30 p.m. to 9:00 p.m.
Enjoy an evening of music featuring the church choir with special guests.
Thursday
May 7
May 7
Romanza: Florida Stories by Florida Storytellers
Thursday, May 7, 2026 | 2:00 to 3:00 p.m.
Ambasador of Storytelling Award winners relate old and new Florida tales.
Thursday
May 7
May 7
Romanza: Kim Bradley, Author—Wine and Cheese Event
Thursday, May 7, 2026 | 3:00 p.m. - 4:00 p.m.
Wine, cheese, and a discussion about the art of writing historical fiction.
Thursday
May 7
May 7
Romanza Festivale: Key of Seas
Thursday, May 7, 2026 | 8:00 p.m. - 9:30 p.m.
Enjoy Flagler College's music ambassadors and a cappella ensemble.
Friday
May 8
May 8
Romanza: First Coast Opera—Baseball Music
Friday, May 8, 2026 | 12:00 p.m. to 1:00 p.m.
Opera vocalists present songs about America's favorite pastime—baseball.
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
Romanza: St. Augustine Concert Band
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 local chorus ends their year-long America 250 trilogy with "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.
Two local vocalists present an intimate evening of story, song, and musical improvisation.
Monday
May 11
May 11
Romanaza Festivale: Romanenko & Kuo
Monday, May 11, 2026 | 12:00 p.m. - 1:00 p.m.
A chamber music concert for cello and violin that's dramatic, witty, and intense.
Tuesday
May 12
May 12
Romanza Festivale: The Elite First Coast Flute Choir
Tuesday, May 12, 2026 | 7:30 p.m. - 9:00 p.m.
A flute concert featuring music from stage and screen—plus popcorn.
Wednesday
May 13
May 13
Romanza Festivale: Classical Guitarists
Wednesday, May 13, 2026 | 12:00 p.m. - 1:00 p.m.
A chamber music concert with classical guitarists Benjamin Brown and Robert Kennedy.
Wednesday
May 13
May 13
Romanza Festival: Yael ZaZa Flamenca
Thursday, May 13, 2026 | 7:30 p.m. - 8:30 p.m.
Join this talented musician performing her concert, "America Without Borders."
Thursday
May 14
May 14
Romanza: Shelly Marsh, Author—Wine and Cheese Event
Thursday, May 14, 2026 | 3:00 p.m. - 4:00 p.m.
Enjoy wine, cheese, and an author's discussion on her nearby inspirations.
Thursday
May 14
May 14
Romanza Festivale: Mama Blue in the Plaza
Thursday, May 14, 2026 | 6:30 p.m. - 8:00 p.m.
Bring your chair and listen to Mama Blue as the sun sets.
Friday
May 15
May 15
Romanza Festivale: Singer Joe Colsant and Pianist M. Giuliani
Friday, May 15, 2026 | 12:00 p.m. - 1:00 p.m.
A chamber music concert with a vocalist and a pianist.
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 pianists "doctors" have performed at home and abroad.
Friday
May 15
May 15
Romanza: St. Augustine Orchestra Spring Concert
Friday, May 15, 2026 | 7:30 p.m. - 9:00 p.m.
The orchestra brings Broadway to town for their final concert of the season.
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 Festivale: The Gainesville Brass Quintet
Saturday, May 16, 2026 | 7:30 p.m. to 9:00 p.m.
Catch a chamber music 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.
Editor's Note: We encourage you to verify event times and details with the organizers, as they may change.
