May is one of the most vibrant months of the year in St. Augustine, Florida. As spring transitions into summer, the city comes alive with major festivals, food events, cultural celebrations, and live music across St. Johns County.

If you’re searching for things to do in St. Augustine in May 2026, here are the top events you won’t want to miss.

Romanza Festivale of the Arts

📅 May 1–17, 2026

One of the biggest cultural events of the year, the Romanza Festivale brings over two weeks of music, art, theater, dance, and live performances throughout the city.

Events are held in a variety of venues — from historic courtyards to concert halls — showcasing St. Augustine’s deep artistic roots.

Why it stands out:

• Multiple performances daily
• Mix of local and national artists
• Free and ticketed events throughout downtown

St. Augustine Food + Wine Festival

📅 May 6–9, 2026

One of the premier food festivals in St. Augustine, this multi-day event brings together top chefs, curated tastings, and elevated culinary experiences across the city.

What to expect:

• Wine tastings and pairing events
• Chef showcases and culinary demonstrations
• VIP and general admission experiences

This is a must-attend for anyone who enjoys great food, wine, and a high-end festival atmosphere.

St. Augustine History Festival

📅 May 6–10, 2026

The St. Augustine History Festival offers one of the most immersive ways to experience the city’s past.

Highlights include:

• Access to historic sites across the city
• Guided tours and reenactments
• Educational exhibits and storytelling

If you’re interested in St. Augustine history or looking for a more meaningful local experience, this is one of the best events of the month.

Blue Crab Festival (Nearby Day Trip Option)

📅 May 22–24, 2026

Just a short drive from St. Augustine, the annual Blue Crab Festival offers a classic Florida waterfront experience with seafood, live music, and family-friendly activities.

Concerts & Live Music at the St. Augustine Amphitheatre

May is also a strong month for live music at the St. Augustine Amphitheatre, one of the top outdoor venues in the country.

Artists performing this month include:

• George Thorogood & The Destroyers
• Ethel Cain
• JJ Grey
• Iration & SOJA
• Willie Nelson
• Sam Barber

This venue continues to be a major draw for both locals and visitors.

Coming Soon: Weekly Summer Traditions Return

While May is packed with major events, it also marks the lead-in to two of the most popular weekly summer traditions that are free to attend:

Concerts in the Plaza

Held weekly on Thursday evenings in downtown St. Augustine, this long-running series features live music in a relaxed, historic setting. This concert series begins May 28th and continues through September 3rd. 

Music by the Sea

Hosted in St. Augustine Beach at the St. Johns County Ocean & Fishing Pier, this event combines live music, food trucks, and ocean views, making it a favorite for locals throughout the summer months. Music by the Sea takes place weekly on Wednesdays, beginning May 20th and continuing through September 23rd. 

Why May Is One of the Best Months in St. Augustine

Between arts festivals, food and wine events, historic celebrations, and live music, May offers one of the most diverse event calendars of the year.

Whether you're:

• A local looking for weekend plans
• A visitor exploring the city
• Or someone considering a move to the area

There’s no shortage of things to do in St. Augustine in May 2026.

It’s this mix of culture, community, and lifestyle that continues to make St. Augustine one of the most desirable places to live on Florida’s First Coast. 

For a full list of local list, visit the local events page on my website.