Discovering the History at St. Augustine, Florida

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Welcome to the oldest city in America! Or, to clarify, the oldest, European-established, continuously-inhabited city in the continental United States. St. Augustine, Florida holds this title after being founded in September, 1565.

While other settlements came before St. Augustine, they were not always inhabited. Some were eradicated by storms, disease or battles with local Native Americans. But, St. Augustine changed that.

Because of its history the city is full of charming relics, old architecture and historic landmarks. I spent a full day here learning of its history and admiring its beauty. Here are my favorite sights and things to do!


When you enter the old city you are met by historic charm and palm trees lining the street. The explorer Ponce de Leon is credited with being the first explorer to claim Florida territory for Spain in 1513. He was on an expedition searching for the Fountain of Youth, and supposedly found it here in St. Augustine.

You can visit the Fountain of Youth in St Augustine. It costs $15 for adults to explore the gardens.

We can thank Pedro Menendez de Aviles for the establishment of St. Augustine. It was actually the capital of Florida for over 200 years, before Tallahassee became the capital in 1824.


St. Augustine has many different parts to the city. There is so much to do here, so I recommend spending 2-3 days here so you won’t be rushed for time. There are a plethora of Bed & Breakfasts right downtown that I recommend, this way you can be right in the heart of the historic district.

Tip: Purchase trolley tickets. You can hop-on, hop-off the trolley all around the city, so you have easy access to all of the sights! It makes travel easy, especially during hot and humid Florida summers.

If you want more budget-friendly accommodation options, look for hotels on the outskirts of the old town. There are hotels near the trolley stations so it is still easy to get everywhere you want to go!


Shop on St. George Street

St. George Street is the main street for shops and tourists. You can find everything from clothes and souvenirs to sweet shops to the oldest schoolhouse in America. I loved walking down the street and wandering in and out of stores. The Spanish architecture and old charm are unique and unlike any place I’ve ever been.

You have to pay to explore the exhibits in and around the schoolhouse, but it’s free to look and take pictures!

Fun Fact: The old schoolhouse actually has no foundation. It sits on a dirt floor and is secured by a very old anchor. By some miracle it’s still standing!


Tour The Castillo de San Marcos 


This Spanish fortress is located right on the water at Matanzas Bay. It is the oldest masonry fort in America, and was used in many sieges before Florida became a state. It became a National Monument in 1924, and you can purchase tickets to take a self-guided tour inside the fort. You have to cross a bridge over what was once a moat to get inside, but from there you can explore the different rooms including the treasury, jail and sleeping quarters. You can even walk up to the roof to see the cannons and the view of the bay.

Tip: It’s a National Monument, so if you have a National Parks pass, four adults can enter for free. Kids 16 & under are free!


Take an Iced Coffee Break

After shopping and exploring in the Florida sun, take a break at this adorable coffee shop! Located next to the Colonial Quarters, it has plenty of refreshing drinks to choose from and a beautiful garden to enjoy your drink in.

Enjoy this part of the city. It has a view of the water and brick streets. You can purchase tickets to go inside the Colonial District, but there’s plenty else to see. You won’t feel like you missed out if you skip the re-enactment.


Tour a Winery

The San Sebastian Winery is a must on any visit to St. Augustine. The tour and tasting is free, and you get to sample quite a few different wines, from their driest to their sweetest, and even two fortified dessert wines.

My Recommendation: Rosa – “The light and refreshing style of this wine is balanced perfectly with a hint of sweetness. The delicate fruity character represents the finest of the Native Florida Muscadine grape.”


Take a Ghost Tour

How can a 450-year-old city not be haunted? Ghost Tours of St Augustine has a variety different tours to choose from, each with a spooky vibe and the chance to spot a few ghosts. This company has been featured on the history channel for its award-winning tours. Try the Haunted Pub Crawl! The tour is $25 and includes your first drink, as well as discounted drinks for the rest of the night.


More Things to Do

If you have more than one day in St. Augustine, here are other great things to do.

Fountain of Youth
This old wise tale is the reason Ponce de Leon embarked on his journey that led him to Florida! Wander through the gardens and check it out for yourself.

St. Augustine Light
A beautiful lighthouse, which can be see across the bay from downtown, is still active today. You can visit the lighthouse and the museum.

Anastasia State Park
You’ll find white sand and blue waters at this state park. It’s perfect for beach goers, but it also has nature trails, campsites, unique wildlife and the Coquina Quarry.

Mission of Nombre de Dios
This mission is a shrine to the Virgin Mary and is recognizable by it’s 240 ft cross. This site hosts America’s first mission, where the first Catholic mass took place.

Flagler College
While the school itself isn’t very old, it’s buildings are. You can tour this college and learn more about its history in St. Augustine.


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