Can’t-Miss Summer Festivals in St. Augustine

From endless days spent relaxing on the beach to nights exploring the city, a St. Augustine vacation delivers on every level. Whether you want to chill or immerse yourself in the culture of the nation’s oldest city, you can do it all, and if you’re looking for some incredible things to add to your itinerary for your upcoming travel, you’ve come to the right spot! Our curated list of can’t-miss summer festivals in St. Augustine covers everything from culinary highlights to 90s throwbacks. Check them all out below as you plan your next visit.

Discover the benefits of booking your St. Augustine getaway directly with Coastal Realty when you view our First Timer’s Guide to Vacation Rentals

St. Augustine Brewers Fest

Person holding beer cup outdoors on a sunny day.

Celebrating its 5th year, the St. Augustine Craft Brewers’ Festival is bringing an afternoon full of innovative craft beer, delicious food trucks, live music, kids’ activities, and more to the Fountain of Youth Archaeological Park! Your ticket grants you unlimited samples from 25+ breweries, highlighting both local and nationwide makers such as Walking Tree Brewery, Southern Philosophy Brewing Co., and Alcatraz Brewing, to name a few. Whether you’re into IPAs, sours, stouts, or blondes, you’ll find something to satisfy your every craving and maybe even a new favorite. Interested attendees should grab tickets now, as this popular event typically sells out. And if you want to enjoy all the fun but skip the beer, Designated Driver tickets are available for just $10.00.

Event Details

When: May 2, 2026 | 1:00 PM – 5:00 PM
Where: Fountain of Youth Archaeological Park
Tickets

Music and Art by the Sea

Each summer, Music and Art by the Sea floods the St. Johns County Ocean Pier with live entertainment and one-of-a-kind creations in a celebration of local talent that’s free and fun for everyone. Taking place every Wednesday except for the hottest month, July, you can enjoy an afternoon filled with food trucks, art vendors, and live musicians as you hang out by the pavilion. Bring your lawn chairs and blankets and soak in the scenery at this beloved St. Augustine summer festival.

Event Details

When: Each Wednesday, May 20 – June 24, and August 19 – September 23 | 3:00 PM – 9:00 PM
Where: St. Johns County Ocean Pier
Tickets: FREE!

St. Augustine Food + Wine Fest

Close-up on a sommelier serving glasses of winetasting event

Foodies, get ready! The St. Augustine Food + Wine Festival returns to the Ancient City for five days of culinary and craft creations from some of the top vintners and celebrity chefs in the business. Full of exciting events like the River Walk Tasting, a BBQ pit-master session featuring beer, wine, and exceptional bites, and the highly anticipated Grand Tasting, it’s a can’t-miss summer festival that keeps people coming back to St. Augustine year after year. Don’t miss this chance to sample some of the best vintages and dishes in one of the most beautiful places in the country.

Event Details

When: May 6-9, 2026
Where: Event Dependent – Various locations throughout St. Augustine
Tickets

Blue Crab Festival

If you’re in town over Memorial Day Weekend, the Blue Crab Festival in Palatka, Florida, is well worth the short drive from St. Augustine. Set on the town’s picturesque riverfront, this family-friendly festival has been going on for 30+ years and features the best seafood in the region. One part music festival, one part food festival, you get the best of both worlds when you visit. Try delicious blue crab in every way imaginable, as well as other tasty seafood creations. The giant kids’ zone features carnival rides and a petting zoo that will keep them busy for hours while you dance to popular bands, and if you’re looking for a vacation keepsake, be sure to check out the local artisans’ booths, too! Whether you take advantage of all three days or just make the trip for one, this summer festival is sure to be the highlight of your Memorial Day in St. Augustine.

Event Details

When: May 22-24, 2026
Where: Riverfront in Palatka, Fl.
Tickets: FREE!

Sing Out Loud Fest

Last year’s Sing Out Loud Fest saw crowds of more than 30,000 people flood Francis Field for a two-day extravaganza featuring the largest stage ever to be erected on the grounds, and this year is expected to be no different. If you’re planning a late summer St. Augustine getaway, this is one festival you won’t want to miss. Headliners haven’t been announced for 2026, but in previous years, the stage has welcomed Noah Kahan, Norah Jones, Father John Misty, Hozier, and more. Get a jump on one of the busiest weekends in St. Augustine, and book your vacation rental while you have your pick of properties! Check out Coastal Realty’s available St. Augustine vacation rentals and secure your festival home base as soon as the dates are released later in March.

Event Details

When: September TBD, 2026
Where: Francis Field
Tickets on sale later in 2026

Book Your Summer Festival Getaway Directly with Coastal Realty

At Coastal Realty, we have an unbeatable selection of St. Augustine vacation rentals guaranteed to deliver everything your family or group needs for an incredible stay. Winner of the Best Property Management Company in St. Augustine award from the Community Choice Awards, you can rest assured our team has your family’s best interest in mind in everything we do. From excellent amenities to our team of local experts, we’re here for you from booking to check out. Plus, when you book your vacation rental directly with Coastal Realty, you also unlock the best rates in the area, so you can keep money in your pocket for your vacation.

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You can even ask us about St. Augustine Vacation Rental Management if you’re looking to invest in a property here!