As spring gracefully melts into summer, St. Augustine blossoms into a vibrant hub of festivals, flavors, and unforgettable experiences. Whether you're drawn to live music, historic reenactments, or world-class culinary events, May offers something magical for everyone. Here’s your guide to the top events lighting up the Nation’s Oldest City this month.
🎭 Romanza Festivale of Music & The Arts
May 2–18 | Various Historic Venues, St. Augustine & Ponte Vedra, FL
Celebrate 17 days of artistic brilliance! With over 75 free and ticketed events—from orchestral concerts and art exhibits to dance and theater—this beloved fest paints the town with creativity and culture.
🍻 St. Augustine Craft Brewers’ Festival
May 3 | Fountain of Youth Archaeological Park
Sip and stroll under the oak trees at this scenic riverside event. Sample unlimited pours from 25+ craft breweries, enjoy tasty bites from local food trucks, and catch live music by Swamptooth. Bonus: It’s family-friendly too!
🎧 As If! The '90s Fest
May 3 | Francis Field
Throw on your neon windbreaker and relive the raddest decade! This nostalgia-packed festival features live bands, retro games, and all things '90s in one totally fly outdoor party.
🕰️ Bartram Living History Festival
May 3 | Alpine Groves Park
Step back in time with reenactments, guided nature walks, and hands-on activities honoring the legacy of explorer and naturalist William Bartram. It’s fun, free, and educational for the whole family.
⛵ Ladybug Race & Waterfront Celebration
May 3–4 | St. Augustine Sailing, Camachee Cove
This whimsical sailboat race is a delight to watch—and even more fun to join! Stay dockside for waterfront festivities, food, and entertainment for all ages.
🌅 Evening at the Estuary
May 8 | GTM Research Reserve
Enjoy live music, local eats, and educational exhibits set against the serene backdrop of the estuary at sunset. It’s a beautiful way to celebrate our coastal ecosystem.
🎶 The Legend of Turandot – First Coast Opera
May 9 | Flagler College Lewis Auditorium
Puccini’s iconic opera comes alive in this grand performance by First Coast Opera. A mesmerizing tale of love, riddles, and destiny awaits.
🍇 St. Augustine Food & Wine Festival
May 7–11 | World Golf Village & Surrounding Venues
Raise a glass at one of the Southeast’s premier culinary celebrations. From celebrity chef dinners to wine tastings and hands-on demos, this multi-day festival is a feast for the senses.
🏛️ St. Augustine History Festival
May 7–11 | Over 35 Historic Sites
Step into the past as you explore centuries-old landmarks and hidden gems. With reenactments, special tours, and engaging talks, this festival is a love letter to the city’s storied legacy.
🎷 Music by the Sea
Wednesdays, May 9–June 25 | St. Augustine Beach Pier Pavilion
Catch ocean breezes and good vibes at this weekly concert series. Bring a beach chair, enjoy the sounds of local bands, and savor bites from on-site food vendors.
☕ Orchestra Afternoon Tea
May 17 | TBD
Indulge in tea and sweet treats as you enjoy a chamber music performance in a sophisticated, serene atmosphere—a perfect afternoon escape.
👑 Rapunzel – St. Augustine Ballet
May 17 | Flagler College Lewis Auditorium
This whimsical ballet brings the beloved fairy tale to life with graceful choreography and enchanting music. A must-see for families and fairy tale lovers alike.
🎺 Jazz Brunch in the Garden
May 18 | Peña-Peck House
Savor your Sunday with gourmet brunch fare and smooth jazz in the lush gardens of this historic downtown home. It’s the ultimate St. Augustine weekend wind-down.
Ready to Experience the Magic of May?
There’s no better time to plan your Staylah getaway. Whether you’re sipping wine under the stars or swaying to seaside melodies, St. Augustine in May is bursting with unforgettable experiences. Let us help you book the perfect stay—browse our handpicked vacation homes designed for comfort, charm, and connection.
