Aerial view of St. Augustine neighborhood

Photo Credit: trolleytours.com

1. Take Advantage of September Locals’ Discounts

September is officially “Locals Month” in St. Augustine, and it comes with some serious perks. St. Johns and Flagler County residents can enjoy free or deeply discounted admission to dozens of attractions. Think of it as the city’s way of saying thanks to its hometown crowd, while also inviting folks to explore places they might usually skip.

Some highlights:

  • Ripley’s Believe It or Not!
  • The Villa Zorayda Museum typically offer 50% off
  • The St. Augustine Alligator Farm gives locals 30% off admission with valid ID.
  • Florida Water Tours rolls out 25% off dolphin, wildlife, and sunset cruises.
  • Many historic sites also participate, meaning you can walk through centuries of history at a fraction of the cost—or even for free in some cases.

Even if you’re visiting from outside the area, it’s still worth keeping an eye out. September often brings bundled passes, seasonal promotions, and even national perks—like free entry to the Castillo de San Marcos on National Public Lands Day (September 27, 2025). Whether you’re a local or not, this month makes it easier to experience more of St. Augustine without stretching your budget.

 

2. Watch the Sun Set from the Water

A view of St. Augustine buildings from the river set against a pink and soft orange sky at sunset, which is reflected in the calm water.

Photo Credit: Floridawatertour.com

There’s just no comparing a St. Augustine sunset to anything else, especially when you’re out on the water. September evenings are warm and breezy, with skies that shift from fiery orange to soft pink as the sun slips behind the skyline and the fort lights up in the fading glow.

Local operators like Florida Water Tours make it easy to enjoy, with dedicated sunset cruises that sometimes include live music or a glass of wine. And if you’re a local, that 25% off September discount is the perfect excuse to finally book one. Dolphins and seabirds are often part of the show, gliding alongside the boat as the day winds down. Visitors, meanwhile, will leave with postcard-worthy memories that capture the city at its most magical.

3. Explore the City’s Historic Sites

Tourists on the rampart of Castillo de San Marcos fort taking pictures next to canons and a watchtower

St. Augustine’s history isn’t just preserved; it’s alive. September’s milder weather makes it the perfect time to walk through the centuries without worrying about the sweltering summer sun. Beyond the popular Castillo de San Marcos, you’ll find treasures like the Colonial Quarter, where you can step into recreated 16th- and 18th-century life, and the Oldest Wooden Schoolhouse, which paints a vivid picture of early education. Smaller gems like the Peña-Peck House or the Old Jail offer even more fascinating stories.

For locals, this is a chance to revisit familiar landmarks and remember just how extraordinary the city’s past really is. For visitors, it’s a chance to walk through layers of history that no other U.S. city can match.

4. Join in the September Festivals

If there’s one thing St. Augustine does well, it’s festivals, and September packs the calendar with them.

The Sing Out Loud Festival runs through much of the month, bringing free and ticketed performances to venues across the city, from intimate bars to the St. Augustine Amphitheatre. It’s one of the biggest music events of the year and offers everything from national acts to homegrown talent.

Founders Day (September 6, 2025) is another September highlight, commemorating Pedro Menéndez’s 1565 landing with reenactments, living history demonstrations, and plenty of family-friendly activities.

If you’re into pop culture, Ancient City Con (September 12–14, 2025) draws fans of comics, games, sci-fi, and cosplay. And to wrap up the month, the St. Augustine Songwriters Festival (September 26–28, 2025) showcases storytelling through music, with performances across multiple venues.

Add in smaller happenings like the Music and Art by the Sea series on select Wednesdays, and September becomes a nonstop celebration of culture, history, and creativity.

5. Stroll Along St. George Street

Image contains people standing outdoors

It’s one of the most visited streets in Florida, but September gives St. George Street a slightly calmer vibe. Without peak-season crowds, you can actually take your time wandering into shops, galleries, and cafés without being shoulder-to-shoulder the whole way.

Grab an iced coffee, browse for unique gifts, or step into a courtyard you might have overlooked before. The mix of modern boutiques and centuries-old landmarks makes St. George Street feel like a walking timeline of the city. For locals, this is the month to rediscover it at your own pace. For visitors, it’s a must-do that captures St. Augustine’s charm in one compact stretch.

6. Discover the Haunted Side of the City

When the sun goes down, St. Augustine’s centuries of history make for some spine-tingling stories. Ghost tours remain one of the city’s most popular evening activities, and September’s cooler nights make them even better.

Lantern-lit walking tours lead you through cobblestone streets as guides recount tales of restless spirits, pirate curses, and eerie happenings in historic cemeteries. If you’d rather sit back, trolley ghost tours let you cover more ground while still getting your fill of chills.

Whether you’re a believer or just along for the storytelling, ghost tours add a fun and spooky twist to your September nights in St. Augustine.

7. Savor St. Augustine’s Culinary Scene

Angled shot of a line of oblong bowls filled with different types of food. The closest bowl is filled with cooked red crawfish.

Food is one of St. Augustine’s greatest pleasures, and September is the time to indulge. You can stick to the classics—like fried shrimp at O’Steen’s or a hearty Cuban sandwich at the Columbia Restaurant—or branch out and try something new.

Seafood lovers shouldn’t miss Caps on the Water, a local institution serving up fresh catch paired with traditional Southern and Mediterranean flavors. Their waterfront location and large outdoor deck, which extends out into the Intercoastal Waterway, provide the perfect way to enjoy scenic St. Augustine views and fine quality local cuisine.

For something trendier, St. Augustine’s food trucks and farm-to-table spots are gaining plenty of buzz. And if you’d like to sample widely, food tours are an excellent way to taste your way through town while learning about the influences that shaped its flavors.

Locals can use September as an excuse to finally book that restaurant they’ve been putting off, while visitors will quickly discover that the city’s food scene is just as rich as its history.

8. Soak Up the Beaches Before Fall

Two children (girl and boy) playing in the waves at the beach.

One of St. Augustine’s best-kept secrets is how enjoyable the beaches are in September. The summer vacationers are mostly gone, leaving behind wide stretches of sand and warm Atlantic waters that are still perfect for swimming.

Anastasia State Park is ideal if you’re looking for natural beauty and a laid-back vibe, with trails, tidal marshes, and a long, undeveloped beach. St. Augustine Beach offers more of a social scene, with its pier, volleyball courts, and nearby restaurants. Vilano Beach brings retro charm, great surf, and postcard-worthy views of the historic district from across the bay.

September’s warm waters and gentler crowds make the beaches the perfect spot to slow down, breathe in the salty air, and enjoy a laid-back day by the ocean.

9. Wander Through Museums and Art Galleries

Lightner Museum Community Open House

St. Augustine’s museums and galleries are as varied as they are fascinating. The Lightner Museum, housed in Henry Flagler’s opulent former hotel, offers an eclectic mix of art, antiques, and curiosities. The St. Augustine Lighthouse & Maritime Museum combines history and adventure, complete with panoramic views if you climb to the top.

For art lovers, the First Friday Art Walk is the place to be. Each month, galleries throughout the historic district open their doors with new exhibits, live music, and refreshments. September’s cooler evenings make strolling between venues all the more enjoyable.

10. Relax and Take It All In

Dinner in the Garden: Hispanic Heritage

Sometimes the best part of September in St. Augustine is simply slowing down. With fewer crowds and milder weather, you can take time to savor the city’s atmosphere.

Sit on a bench along the bayfront and watch the boats glide by. Linger over coffee in a hidden courtyard. Let a street musician’s guitar provide the soundtrack to your evening. The cobblestones, the Spanish architecture, the salty air—it all blends together into something uniquely St. Augustine.

Whether your September days are packed with festivals or spent lounging by the water, one of the best ways to enjoy St. Augustine is by simply letting the city set the pace.

Wrapping It Up

September might just be the best-kept secret in St. Augustine. It’s a month of discounts, festivals, beach days, and delicious meals, all wrapped up in the laid-back vibe of early fall. Locals get the joy of being tourists in their own town, while visitors get to experience the city at its most authentic and welcoming.

From music festivals and Founders Day celebrations to ghost tours and quiet sunsets on the water, St. Augustine in September is rich with ways to enjoy the season. All that’s left is to pick your favorites, use our calendar to mark yours, and let the oldest city in the nation show you why September is something truly special.

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