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See the Best of St. Augustine, Florida: Hop Aboard The Old Town Trolley Tour!

Writer's picture: Chrissa KarnesChrissa Karnes

Green and orange trolley on a street in St. Augustine with "Old Town Trolley Tours" logo. Trees and house in the background, clear sky.

St. Augustine, Florida, is filled with history, charm, and beauty, and there’s no better way to explore this city than on the Old Town Trolley Tour. I’m sharing all the details about this must-do tour that will take you on a journey through the heart of St. Augustine. From historical landmarks to scenic views, this tour is the perfect way to experience the oldest city in the United States.


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What is the Old Town Trolley Tour?


People ride an open tram on a sunny street, passing a yellow building with white balconies. Signs read "Please exit backwards."

The Old Town Trolley Tour is a narrated, hop-on, hop-off tour that stops at over 20 different points of interest around St. Augustine. The beauty of this tour is that you can get on and off at any stop as often as you’d like, all day long. It’s the best way to explore the city while learning about its rich history and experiencing the charm of its streets, landmarks, and attractions.


Highlights of the Old Town Trolley Tour Stops


Stop 1: Old Town Jail & Main Depot


People gather outside a red historic building, with an "Old Jail" sign. A figure in striped attire stands at a cart, under a clear blue sky.
St. Augustine History Museum exterior with beige walls, arched windows, and wooden benches. Signage visible; bright sunny day.

Old-style building with "General Store" faded sign, bright blue sky. "Oldest Store Museum Experience" sign below, greenery on porch.


People at Gator Bob's Trading Post entrance; signs for gifts, ice cream, and arcade. Bright sunny day with a relaxed, cheerful atmosphere.

Our journey begins at Stop 1, the Old Town Jail & Main Depot. Here, you’ll find free parking and the chance to purchase tickets to the trolley and other attractions at a discount.


At Stop 1, you can explore several must-see spots including:


  • The Old Jail, built in 1891, which served as the county jail until 1953 and was financed by Henry Flagler, a key figure in Florida’s tourism development.

  • The Oldest Store Museum Experience

  • St. Augustine’s History Museum

  • Gator Bob’s Gift Shop and Penny Arcade


After exploring these attractions, hop aboard the trolley to continue your adventure.


Stop 2: Visitor Information Center


Entrance to St. Augustine info center with wooden floors, banners, and costumes. A poster reads "Explorer's Passport Available Here."

The Visitor Information Center is a great place to grab a map, ask questions, and get recommendations for the rest of your day in St. Augustine. Here, you can also view exhibits featuring artifacts from both the Spanish and British Colonial periods.


Stop 3: Potter’s Wax Museum


Potter's Wax Museum exterior with red sign. Old wooden building, statue seated outside. Sign reads "America's First Wax Museum."

Next, we stop at Potter’s Wax Museum and Authentic Old Drugstore, the first wax museum in the U.S. featuring over 160 life-like figures, including historical icons and modern celebrities. It’s a fascinating stop for anyone interested in the art of wax sculpting.


Stop 4: City Gates


Stone gate with two tall pillars under a clear blue sky. Trees and grass surround the historical site, creating a peaceful atmosphere.

At Stop 4, you’ll visit the iconic City Gates, built in 1808 as part of the city’s defense. These stone columns were once the only entrance into St. Augustine. Nearby, you’ll find St. George Street, a pedestrian mall lined with restored buildings, shops, restaurants, and museums. Make sure to stop by the Oldest Wooden Schoolhouse, built over 200 years ago!


Stop 5: Colonial Quarter & Pirate & Treasure Museum


Jolly Roger flag with skull and crossbones in a wooden display, labeled "Original Jolly Roger - 1850." Bottles are on the shelf below.

Stop 5 brings us to the Colonial Quarter, where the Pirate & Treasure Museum awaits. This museum is a must-see for anyone fascinated by the golden age of piracy. It showcases over 600 real pirate artifacts, including the only surviving pirate chest from Captain Thomas Tew and an original Jolly Roger pirate flag.


More Must-See Stops on the Old Town Trolley Tour


Stop 6: Matanzas Bayfront


People walk near a large wooden ship with flags in a sunny park setting. Blue sky, green grass, and a bridge in the background.

At Stop 6, enjoy stunning views of the bay from the Best Western. This scenic spot offers great photo opportunities, including views of the Bridge of Lions.


Stop 7: St. George Street


People walk on a sunny street lined with rustic buildings and a palm tree. Signs read "Auggie's Draft Room" and "Burgers." Casual, relaxed scene.

Old wooden schoolhouse with chained roof, a sign reading "The Oldest Wooden School House," two people at the door, and flower wreaths.

Take a leisurely stroll down St. George Street, the heart of St. Augustine’s historic district. This pedestrian-only street is lined with unique shops, restaurants, and historic buildings, making it the perfect place to shop or grab a bite to eat.


Stop 8: Iconic St. Augustine Churches


Historic church facade under clear blue sky, featuring stained glass windows and intricate stonework. Palm trees and parking sign in foreground.

At Stop 8, explore some of the city’s most beautiful churches:


  • Flagler Memorial Presbyterian Church: A stunning example of Spanish Renaissance architecture.

  • Ancient City Baptist Church: A castle-like design that stands out in the skyline.

  • Grace United Methodist Church: A Romanesque Revival beauty funded by Henry Flagler.


Stop 9: Villa Zorayda Museum


Villa Zorayda Museum in ornate Moorish style, red and tan facade, lush palm trees, sign with text in foreground under clear blue sky.

The Villa Zorayda Museum at Stop 9 is a Gilded Age mansion inspired by the Alhambra Palace in Spain. Inside, you’ll find a collection of art and antiques, including the ancient Sacred Cat Rug.


Stop 10: Lightner Museum & Flagler College


Lush courtyard with tall palm trees, greenery, and a fountain, surrounded by a historic building under a clear blue sky.

Statue of a man in front of arched entrance to Flagler College. Red brick, ornate details, and palm trees in the background.

Ornate building with red accents and two towers under a blue sky. Central fountain, palm trees, and greenery create a serene atmosphere.

At Stop 10, visit the Lightner Museum, once the Alcazar Hotel built by Henry Flagler. Now home to 19th-century art and antiques, it’s a fascinating look at the Gilded Age. Across the street, Flagler College impresses with its Spanish Renaissance architecture and Tiffany stained glass windows.


St. Augustine’s Best Stops for History and Views


Stop 11: Lincolnville Museum and Cultural Center


Two-story house with a sign reading "The I Have A Dream House." White exterior, blue trim, palm tree, chain-link fence, sunny day.

Stop 11 takes us to the Lincolnville Museum and Cultural Center, a place that honors St. Augustine’s Civil Rights history. The area played a significant role in the passage of the Civil Rights Act of 1964.


Stop 12: St. Augustine Distillery


Black truck parked outside St. Augustine Distillery. White brick building with whiskey, rum, gin, vodka signs. Blue sky above.

At Stop 12, the St. Augustine Distillery offers free tours where you can see how small-batch spirits are made from local ingredients. Be sure to sample their award-winning bourbon, vodka, gin, and rum!


Stop 13: San Sebastian Winery & Whetstone Chocolates


A wooden figure in a t-shirt stands by wine tanks with a "San Sebastian Winery Tour & Wine Tasting" sign. Industrial setting, bright day.

Enjoy a complimentary wine tasting at San Sebastian Winery at Stop 13, or indulge your sweet tooth with a tour at Whetstone Chocolates, just a short walk away.


The Final Stops of the Old Town Trolley Tour


Stop 14: Plaza de la Constitución


Plaza de la Constitucion with a statue, palm trees, and a gazebo under a clear blue sky. Text reads "Plaza de la Constitucion Stop 14."

At Stop 14, visit the historic Plaza de la Constitución, surrounded by beautiful architecture like the Government House and Cathedral Basilica. It’s the heart of downtown St. Augustine and a great spot for exploring.


Stop 15: Oldest House


Historic two-story house with green shutters, labeled "The Oldest House." Two flags are hung outside. Clear blue sky, trees nearby.

The Oldest House, built in the early 1700s, is the oldest surviving Spanish colonial dwelling in St. Augustine. A guided tour offers fascinating insights into the lives of the families who once lived here.


Stop 16: St. Augustine Marina


Brick structures with tiled roofs, signs for Ripley's Mini Golf and "No Trespassing." Palm tree and ship visible under a clear blue sky.

Stop 16 brings us to the St. Augustine Marina, a great spot to relax by the water or take a scenic cruise along the Matanzas River. You can also enjoy mini golf at Ripley’s Bayfront Mini Golf nearby.


Stop 17: Castillo de San Marcos


Ancient stone fort by a river, with a bridge and boats in view. Palm trees line the sandy path. Flag flutters; people explore the site.

One of the most iconic landmarks in St. Augustine, the Castillo de San Marcos, is the oldest masonry fort in the continental United States. Explore the fort’s history, bastions, and breathtaking views of the bay.


Stop 18: Ripley’s Believe It or Not


Historic building with arched windows, labeled "St. Augustine's Ripley's Believe It or Not! Museum." Clear sky, palm trees, manicured garden.

Stop 18 brings us to Ripley’s Believe It or Not, housed in a historic castle-like building. This quirky museum features over 800 exhibits filled with oddities and curiosities from around the world. It’s a fun stop for all ages, with something for everyone to enjoy.


Stop 19: Old Town Trolley Welcome Center


Two people board a green Old Town Trolley under a clear blue sky. An American flag waves above, with a building in the background.

At Stop 19, you’ll find the Old Town Trolley Welcome Center, where you can purchase tickets, get more information about the tour, and plan the rest of your adventure in St. Augustine.


Stop 20: Mission of Nombre de Dios


Pathway leading to a large cross among trees under a clear blue sky. Signs say "Bienvenido!" in a green park setting with a pond.

Stop 20 takes us to the Mission of Nombre de Dios, the site of the first Catholic mass in what is now the United States. This peaceful and spiritual site features beautiful grounds, a historic chapel, and the Great Cross, which stands 208 feet tall.


Stop 21: Old Senator Tree & Howard Johnson Hotel


Large oak tree in a paved plaza, surrounded by a black fence. An American flag and a sign reading "The Old Senator" are nearby. Bright day.

At Stop 21, visit the Old Senator Tree, one of the oldest live oaks in the country, standing at over 600 years old. The tree has witnessed centuries of history, including the time of Ponce de Leon and Martin Luther King Jr. Nearby, you’ll also find the Howard Johnson Hotel and Magnolia Avenue, which is often called one of the most beautiful streets in the country.


Stop 22: Fountain of Youth


Entrance to the Fountain of Youth with ornate peacock arch, surrounded by lush greenery. Open wooden doors lead inside. Mood is inviting.

The final stop on the tour is the legendary Fountain of Youth, Florida’s oldest attraction. This historic site commemorates Ponce de Leon’s 1513 landing and quest for the Fountain of Youth. Explore the beautiful grounds, drink from the spring, and enjoy the company of the many peacocks that roam freely.

Tips for Your Old Town Trolley Tour Experience


  • The tour spans 8.5 miles and lasts around 90 minutes, but since it's a hop-on, hop-off experience, you can take your time at each stop.

  • You can start the tour at any of the 22 stops and hop off and back on as you please.

  • The tour operates 364 days a year, with the exception of Christmas Day.

  • For those interested in St. Augustine’s haunted history, there’s the Ghosts & Gravestones Tour, which is available nightly. Reservations are required for this spooky experience.


Conclusion: A Historic St. Augustine Adventure Awaits


St. Augustine is filled with rich history, beautiful landmarks, and charming streets to explore. The Old Town Trolley Tour is the perfect way to discover everything this city has to offer, from iconic forts to hidden gems. Make sure to check out my guide to Castillo de San Marcos for a deeper dive into one of St. Augustine's most iconic sites.


If you're planning a trip to St. Augustine, don’t forget to check out my other blogs for tips and guides to help you make the most of your visit.

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