Baby alligator, photographed at 'gatorpark' in Orlando, Florida. Photo by Sieuwert Otterloo, Unsplash

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Mythical springs, prehistoric alligators, Spanish forts, trolley tours.

Am I sharing the headline for a new adventure theme park?

No, readers. I’m talking about America’s oldest city.

Welcome to St. Augustine.

What (and where) is St. Augustine?

Located 40 miles south of Jacksonville in St. John’s County, Florida, St. Augustine is the oldest continuously habited city of European and African-American origin in the United States.

Yes, this means St. Augustine’s founding predates the English colonization of Jamestown!

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Founded in 1565 by Spanish conquistador Pedro Aviles (42 years before Jamestown), St. Augustine served as the capital of Spanish Florida for 200 years. Today, St. Augustine’s distinct Spanish architecture and historic downtown center attract thousands of tourists and potential homeowners each year.

But, there is much more to see in this mystical town than the town center and haunted trolley tours (which are really fun, by the way!). From the Fountain of Youth to Alligator ziplining, there’s something for everyone in this seemingly timeless Spanish-tiled hamlet.

Stick with me as I walk you through the top 10 things to do in America’s oldest city.

Fountain of Youth. Photo by Aurie Ceylon
Fountain of Youth. Photo by Aurie Ceylon

1. Ponce de Leon’s Fountain of Youth

Remember that whole Fountain of Youth thing? For the history buffs (and mystical believers), this is a must-see!

Brief History Lesson: The Fountain of Youth is a mythical spring rumored to restore youth and vitality to anyone who drinks or bathes in its waters. Tales of this magical elixir date as far back as the Crusades (11th/12th century, AD).

The legend attracted the attention of adventurer and first Governor of Puerto Rico, Juan Ponce de Leon. Ponce de Leon is rumored to have been searching for the fountain when he traveled to Florida in 1513, where he came upon the original inhabitants of St. Augustine – The Timucua people.

The Timucua village was centered around the magical spring, which was later claimed as The Fountain of Youth by Spanish settlers. While no evidence exists, modern-day historians connect Ponce de Leon to the Fountain of Youth, saying that his exploration later led to the discovery of the long-rumored mystical spring.

What to do at the Fountain of Youth? The journey through this moss-covered 15-acre archaeological park includes a walking history tour to the suspected (but never officially proven) site of Ponce de Leon’s landing in 1513.

Stroll the grounds on your own, or chat with one of the historians on-site for an interactive telling of years gone by.

Before you leave, grab a cup of what has been called “the elixir of life” from the Fountain of Youth. Travel bottles are available at the Fountain of Youth gift shop, so you can share eternal vitality with your family and friends.

For the adventurer: You can actually drink the mysterious Fountain of Youth water straight from the spring! It smells awful, but that might be the price of everlasting life…

Click to learn more about The Fountain of Youth

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Castillo de San Marcos, St.Augustine, United States. Photo by Sahi S, Unsplash
Castillo de San Marcos, St.Augustine, United States. Photo by Sahi S, Unsplash

2. Castillo de San Marcos National Monument

Calling all wanderers! This is the spot for you. Check out this historic (and eerie) relic, which sits oddly placed at the center of this otherwise adorable town. Located on the Matanzas River, this understated yet ostentatious waterfront national monument is pretty hard to miss.

Brief History Lesson: Built in the 1670s by the Spanish, this is the oldest masonry fortification in the United States. Construction began after much of St. Augustine (including the original wooden fort) was destroyed after a raid in 1668.

The construction of the core was completed by the 1690s, but the fort went through many updates (and owners) in the centuries ahead. Flip-flopping between British and Spanish rule for centuries, it was renamed Fort Mark in 1763, then changed to Fort Marion in 1821.

Finally, the fort was renamed Castillo de San Marcos and declared a National Monument in 1924 before being officially deactivated in 1933. Today, the fort stands as a publicly accessible historic site for tourists and curious historians alike.

What to do at Castillo de San Marcos? Stroll the grounds and imagine 17th-century life, chat with a ranger or historian, watch a musket or cannon demonstration, or take the reins and explore every nook and cranny of the fortress yourself.

Click to learn more about Castillo de San Marcos

Alligator and reflection in St Augustine, Florida. Photo by Jonathan Mast, Unsplash
Alligator and reflection in St Augustine, Florida. Photo by Jonathan Mast, Unsplash

3. St. Augustine Alligator Farm & Zoological Park

Yes, an alligator farm.

Truly, readers, I didn’t know what to expect, but whoa. This alligator farm feels like you’ve stepped into the 1996 cult classic Jurassic Park. What started as a small attraction in 1893 has evolved into a tropical metropolis for crocodilians, reptiles, birds, and more.

Brief History Lesson: Today, this St. Augustine must-see’s claim to fame is its wide and varied assortment of gators, but back when it was a growing business in the 1890s, the alligators were an added bonus to bring in curious tourists.

When the beachfront park’s “Come for the gators, stay for the souvenirs!” angle picked up, the park switched owners and moved to its current location on Anastasia Boulevard.

After a devastating fire in the 1930s, the park once again rebranded and expanded, this time focusing more on reptiles and later becoming the first place in the world to display every species of crocodilians.

What to do at the Alligator Farm? Readers, there’s so much to do, it’s hard to imagine fitting it into one day. Catch a wildlife show, explore nature exhibits (don’t forget the tortoises!), or take a chance and walk across the ‘alligator boardwalk’, if you dare.

For risk takers: Tempt the fates and try ziplining over the alligator swamp!

Click to learn more about St. Augustine Alligator Farm & Zoological Park

This is the oldest wood schoolhouse in the United states found in St. Augustine, Florida dating back to the 1600s. Photo by Philip Arambula, Unsplash
This is the oldest wood schoolhouse in the United states found in St. Augustine, Florida dating back to the 1600s. Photo by Philip Arambula, Unsplash

4. St. George Street

Ever wanted to star in a Hallmark movie?

Look no further than this historic and picturesque shopping street, full of intimately lit boutiques and cafes.

Stroll up and down the winding cobblestone streets, which take you from the historic town center all the way to the marina.

Brief History Lesson: In its earliest days, St. George Street was St. Augustine’s town center and is still referred to as the “heart” of the town. Located smack dab in the middle of historic downtown, St. George is packed with tourists and residents, rain or shine.

Along with endless shops, bakeries, restaurants, and cafes, this pedestrian-only walkway is chock full of interest and oddities, including the Oldest Wooden Schoolhouse in America (pictured above) and the Medieval Torture Museum!

If you don’t stop along the way for at least one crepe, you’re doing it all wrong.

Night of Lights. Photo by Aurie Ceylon
Night of Lights. Photo by Aurie Ceylon

5. Night of Lights

Get your holiday rom-com movie moment!

From mid-November through the end of January, stroll up and down every street of historic downtown St. Augustine for a breathtaking holiday spectacular!

Ranked by National Geographic as one of the top 10 places in the WORLD to see holiday lights (yes, the world!), the Night of Lights is truly something to see…literally.

Featuring thousands of lights on dozens of local businesses, take in miles of splendor and garland-wrapped magic on restaurants, shops, hotels, and bed & breakfasts.

Walking not your thing? No worries, readers. Hop on the Night of Lights Trolley Tour.

The 30th Annual Night of Lights runs in St. Augustine until January 28, 2024.

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6. Drive-ON Beach

Yes, on the beach. No more walking for ages from the beach parking lot. Grab your motor vehicle and hit the sand.

Take in breathtaking views of Saint Augustine’s white sandy shoreline with your mode of transport close behind. Park and take in the sights, or drive up and down the shoreline.

Columbia Restaurant. Photo by Aurie Ceylon
Columbia Restaurant. Photo by Aurie Ceylon

7. Columbia Restaurant

Welcome to “Florida’s oldest restaurant!”

If you’re dining in historic St. Augustine, you have to get to Columbia. Located in the center of everything Hallmark historic, this Spanish restaurant has been in business since 1905.

With charming nooks and crannies, fountains, and intricate Spanish tile, it feels like dining in a 17th-century castle.

Even the menu oozes with old-world charm. The decor is so well-renowned, you can leave with a hand-painted, keepsake Sangria pitcher!

Get the Paella. Trust me.

Click to learn more about Columbia Restaurant

8. St. Augustine Pirate & Treasure Museum

It wouldn’t be America’s oldest city without some pirates, would it?

No, readers, it would not.

With a deep-rooted history in swashbuckling, it’s no surprise that the St. Augustine Pirate & Treasure Museum is a MUST for all adventurers and history buffs.

Brief History Lesson: Founded in 2005 by Pat Croce, mogul and entrepreneur, the museum was originally located in Key West and featured many artifacts from Croce’s personal collection.

In 2010, Croce decided to move the museum to St. Augustine, where it currently sits directly across the street from Castillo de San Marcos! The museum displays one of the largest collections of pirate artifacts and is an intimate and bustling site for tourists and St. Augustine residents.

What to do at the Pirate & Treasure Museum? This interactive history museum will transport you back to the Golden Age of Piracy in Port Royal, Jamaica.

Visitors can learn about infamous pirates including Sir Francis Drake, Robert Searles, and many others who were integral to the history of piracy in colonial America.

The museum is full of curiosities for all ages, including the sword used by Johnny Depp (aka Jack Sparrow) in Disney’s Pirates of the Caribbean!

Click here to learn more about the Pirate & Treasure Museum

9. The Old Jail

Ever wondered what life was like as a 19th-century prisoner?

Look no further than The Old Jail (yes, that’s really the name!), St. Augustine’s most criminal attraction.

Brief History Lesson: The Old Jail was constructed in 1891 and financed by Henry Flagler. Originally built to house (or confine?) 72 prisoners across various wings – including a death row cell – The Old Jail is full of mysteries and oddities for anyone who loves true crime.

What to do at The Old Jail? Check out The Old Jail Museum and explore a restored jail cell and the sheriff’s living quarters! The museum also contains weaponry and a more-than-creepy pictorial collection of hangings.

The Old Jail is also the final stop for The Old Jail After Dark trolley tour, where visitors (and paranormal investigators) spend hours exploring the mystical – and possibly haunted – building.

Click to learn more about The Old Jail

10. Colonial Quarter

Historical reenactments? Yes, please.

Walk through this immersive “living museum” and catch a glimpse into 17th and 18th century life in America’s oldest city.

Brief History Lesson: Originally titled, “The Colonial Spanish Quarter”, this living museum was opened in 1963 as a way for visitors to experience America’s oldest city under Spanish rule in the 1740’s.

It operated on a two-acre site and was owned by the University of Florida until 2011, when it was remodeled and branded as “Colonial Quarter” and moved to its current location on St. George Street.

Since reopening in 2013, Colonial Quarter is known for its immersive and interactive historical features, as well as its outdoor music venue!

What to do at Colonial Quarter? Come for the history, stay for the tunes! Spend the day exploring (and interacting) with costume-clad historical guides and volunteers, then sit outside and enjoy live music, which plays nightly on Colonial Quarter’s stage.

Don’t forget to check out panoramic views from the watchtower!

Click here to learn more about Colonial Quarter

Final Thoughts

This New York Girl will find any and every excuse to go to Florida! While Disneyworld is great, I’m always there for one thing…St. Augustine. My family and I love finding new and interesting ways to explore America’s oldest city.

Even as I write this article, I find myself reinvigorated – There is SO much to explore! From the Fountain of Youth to swashbuckling pirates to gator boardwalks to creepy haunted prisons…St. Augustine has all of the magic and mysticism I need to have a stellar adventure.

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Author Bio: Aurie Ceylon is a writer, reader, and traveler from New York City. A quirky and self-proclaimed “smarty pants adventurer”, Aurie writes detailed exploits of her travels, eats, and love & relationship blunders on her blog – hey, it’s aurie! 

Aurie is finding happiness through her travel adventures. Stick with Aurie as she fills her heart – and stomach – in small towns across America.

Follow Aurie on Instagram to see more of her travel content! IG: @heyitsaurie

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