In honor of our 16th anniversary of owning Bayfront Marin House, we’re sharing 16 of our favorite things to do in St. Augustine this fall. Since purchasing the inn on September 1, fall has always held a special place in our hearts. From historic tours and live music to spooky attractions and seasonal festivals, here are some of our favorite ways to experience St. Augustine this beautiful time of year.
Flagler Legacy Tours
A Flagler College tour is our hands-down favorite historic tour in St. Augustine, and September is the perfect time to go. Tours are led by current Flagler students, so the schedule changes around school holidays and breaks. They’re back again in the fall.
Tours begin in the college’s Rotunda at 74 King Street and take you through the former Ponce de Leon Hotel. Look up at the 68-foot dome covered with stunning paintings, admire the intricate mosaic floors, and look around at the many carved wooden pillars. You’ll also see the student dining hall, home to 79 Tiffany glass windows, and the courtyard with its working sundial.
Lightner Museum and Cafe Alcazar
Fall can still bring afternoon rain in St. Augustine, so museums are a great option when the weather turns. If it’s warm, you’ll appreciate the air conditioning, and if a shower rolls through, you can stay dry while exploring.
The Lightner Museum, located inside the former Alcazar Hotel in the heart of downtown St. Augustine, is one of our favorites. Café Alcazar is located inside the hotel’s former indoor swimming pool. It’s a lovely spot to relax after exploring the museum, and they often feature live music.
St. Augustine Distillery Tour
The St. Augustine Distillery offers a fun look at the history of distilling in Florida and the local farmers who help make the craft spirits industry possible. The $5 tour is well worth it, and tastings are included.
Don’t miss the gift shop at the end, which is full of St. Augustine themed souvenirs.
First Friday Art Walk
Held on the first Friday of each month, First Friday Art Walk is a monthly celebration of art throughout St. Augustine. From 5 to 9 p.m. more than 25 galleries across downtown, Aviles Street, Anastasia Island, and surrounding areas open their doors, often with wine, music, and light bites.
One of our favorite spots is Aviles Street, which is lined with galleries and artisan shops, including our own Casita de Aviles and Aviles Street Cottage.
Zipline Over Alligators
We love the St. Augustine Alligator Farm, and it’s not just about the alligators. Just this morning, we got caught up watching turtles eat watermelon, and it was worth the trip just for that.
If you’re craving adventure, the park also offers two different zipline courses above the alligator habitats. Don’t worry if you’re new to ziplining. Your tour begins with a test run just five feet off the ground before you take to the skies.
Catch a Concert
St. Augustine has an impressive live music scene, and fall is one of our favorite times to enjoy it. We’re especially excited about the recently renovated and expanded Ponte Vedra Concert Hall, less than 20 minutes north of our Vilano Beach cottages.
Of course, don’t forget about the St. Augustine Amphitheatre, right across the Bridge of Lions from the inn. And if you’re visiting in September, the Sing Out Loud Festival is one of the biggest music events of the season. In 2026, the festival features more than 160 acts performing at venues throughout St. Augustine, with local artist showcases running throughout September.
If you’re planning your trip around the festival, check out our tips for surviving and thriving at Sing Out Loud in St. Augustine and our guide to the best live music in St. Augustine.
Photo Credit: Kram Kran Photography
Sip Out Loud
If you love good wine, food, and live music, add Sip Out Loud to your September plans.
Guests can visit four wine stations featuring wines from multiple wineries and meet Talisman Wines proprietress Marta Rich, who will be sharing the stories behind her wines. Local restaurants will also serve tasting portions throughout the courtyard, giving you plenty to enjoy alongside the wine and live music.
Even better, Sip Out Loud is just steps away from the Sing Out Loud Singer-Songwriter Festival, so you can easily keep the evening going after the wine and food portion wraps up. With limited public tickets available, check the Sip Out Loud website for the latest information.
Cuddle a Capybara
If you’re traveling with an animal lover, you’ll want to book a capybara encounter at the Capybara Café in St. Augustine. You’ll spend time with these lovable creatures, as well as an armadillo, skunk, and several ferrets.
This isn’t a petting zoo. The animals choose whether to cuddle or wander, and groups are kept small. Buy your tickets in advance.
Visit the Big Cats
If big cats are more your style, head north to Catty Shack Ranch Wildlife Sanctuary. This nonprofit rescue takes in animals that have been abandoned, neglected, or abused, including lions, tigers, jaguars, and leopards.
All donations go toward their care, and if you can catch a tiger bubble bath, get ready for cuteness overload!
Learn a New Skill
Instead of bringing home a keychain, why not bring home a new skill? Head to 36 Granada in downtown St. Augustine, a beautifully renovated multi-use space. On one side is the French Pantry, on the other is Little Miss Ha, with a shared bar area where you can order from either menu.
Behind both restaurants is La Petite Kitchen, which offers cooking classes throughout the year. Learn to make Italian pasta, Vietnamese spring rolls, or other specialties from featured chefs.
Hide Out in a Speakeasy
St. Augustine has plenty of great places for a drink, but we especially love the hidden ones. The Tipsy Duck Parlor at 58 Hypolita Street is tucked inside Bath Junkie. Use the side door, and you’ll find drinks served in plastic bathtubs and barstools with duck feet. Even kids are allowed, making it a quirky and fun stop.
For something especially unique this fall, don’t miss the Velvet Underground Show, running late September to early October. This immersive pop-up experience at Arts N’ Motion on San Marco Avenue features live musicians, dancers, aerialists, and a Vegas-style show.
For a speakeasy with food, cross the Bridge of Lions to Odd Birds Café, where the hidden entrance is tucked behind a bookcase. Shh… it’s a secret!
Historic House Tours
This is what St. Augustine, Florida, is best known for! The city is filled with historic homes, many of which are within walking distance of downtown attractions. Some favorites include the Pena-Peck House, Ximenez-Fatio House, Llambias House, Father Miguel O’Reilly House, and the Oldest House.
You can even stay in history. Our Jose Simeon Suite is one of the few Second Spanish Period homes in St. Augustine that isn’t a museum. With hand-hewn beams, handmade cabinets, and modern comforts including a new bath and flat-screen TV, it’s one of the few historic homes from the Second Spanish Period where you can actually spend the night.
Take a Spooky Tour
It makes sense that the oldest city in the U.S. has plenty of ghost stories. October is the perfect time to explore them! Options include the Ghosts & Gravestones Trolley Tour, candlelight tours of the Ximenez-Fatio House, nighttime visits to the Old Jail, and tours of Villa Zorayda, where you’ll find some truly unusual pieces of history.
For another seasonal option, look for October tours and events at the Ximenez-Fatio House, including its Halloween programming.
Whetstone Chocolate Factory & San Sebastian Winery
Start your afternoon at the Whetstone Chocolate Factory on King Street, where you’ll learn about the history and craft of chocolate making. Then stroll to San Sebastian Winery for a tasting.
For dinner, head upstairs to La Cocina at the Cellar Upstairs, where you can enjoy delicious food and one of the best sunset views in St. Augustine.
Relax on the Schooner Freedom
Fall is the perfect season for a sunset sail aboard the Schooner Freedom, which departs from St. Augustine’s City Marina, just a five-minute walk from our inn. Enjoy the breeze, a drink, and views of the historic waterfront from the ship.
Frolic at a Fall Festival
Fall brings festivals, music, art, food, and special events throughout St. Augustine. Some of our favorite 2026 events include:
- First Friday Art Walk: Sept. 4, 2026, and the first Friday of each month, 5–9 p.m.
- Aviles Street Festival: Sept. 5, 2026, noon–8:15 p.m. – Celebrate St. Augustine’s connection to Spain.
- Sing Out Loud Festival: Sept. 4–27, 2026 – Free and ticketed music events throughout St. Augustine.
- St. Augustine Heritage Book Festival: Sept. 19, 2026 – Ximenez-Fatio House.
- Sip Out Loud: Sept. 24, 2026, 5–8 p.m. – Wine, food, music, and art at Bin 39.
- Record Fair: Sept. 27, 2026, 11 a.m.–3 p.m. – More than 30,000 music collectibles at the St. Augustine Amphitheatre.
- Pink Up the Pace 5K: Oct. 3, 2026 – Downtown St. Augustine.
- Halloween Trick-or-Treat Festival: Oct. 24, 2026, 1–4 p.m. – Family-friendly Halloween fun at the Ximenez-Fatio House.
- Velvet Underground Show: Sept. 24–Oct. 3, 2026 – Immersive live entertainment at Arts N’ Motion.
- Whiskey, Wine & Wildlife Festival: Nov. 6–8, 2026 – Vilano Beach.
- Nights of Lights: Nov. 21, 2026–Jan. 18, 2027 – St. Augustine’s historic downtown comes alive with holiday lights.
Event dates and details can change, so it’s always a good idea to check with the event organizer before making plans.
