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One Day in St. Augustine | Itinerary

October 29, 2022 8 min read

There are so many beautiful cities in Florida, but if there is one that I absolutely love, it is St. Augustine. Full of history and attractions, St. Augustine is a must-visit destination.

Since this beautiful city is an hour and a half away from Orlando, my partner and I decided to go for a day. Although I recommend staying a few days in the city to see and do everything they have to offer, going for a day can also be worthwhile.

If you’re planning to go for a day, check out my itinerary below.

One Day in St. Augustine

Since my partner and I have been to many of the attractions in the past, we opted out of going to some of the most popular places. Instead, we went to the ones we hadn’t been to before.

Our morning started by arriving around 10 am, which is why we didn’t get any breakfast in the area. However, there are many wonderful cafes in the area for a good breakfast, if you’d like a few recommendations, see my ultimate guide.

St. Augustine

Old Town Trolley Main Station

When we arrived in St. Augustine, the first thing we did was go to the Old Town Trolley Main Station on San Marco Ave. They have free parking in that area and a few attractions to check out as well. Once we parked, we got our tickets to get on the Old Town Trolley and visit the Authentic Old Jail.

Address: 167 San Marco Ave.

St. Augustine

Authentic Old Jail

Once we got our tickets, we waited for a couple of minutes outside the Authentic Old Jail until we had a big group of people. In the beginning, you will have a guide taking you inside the building. The guides are dressed as prisoners, which is such an experience, and as you explore the old jail, you’ll hear the history and some stories about this place.

While the tour is fun and the tour guides do such a good job to remain in character as prisoners, the history of the Authentic Old Jail is a sad one.

The concept of the jail began in 1891 when Henry Flagler contracted a company to build the jail. This same company would eventually build Alcatraz. While the outside of the building is absolutely beautiful, the inside is not. Built to house about 72 prisoners, the jail consists of a general area, a maximum security area, and a women’s section with a lower-level kitchen. The building also consists of an office for the sheriff with living quarters for his family.

St. Augustine

As we walked through the prison and the living quarters, I tried to imagine what it would be like to live near the prisoners, especially the dangerous prisoners that were confined in maximum security. Honestly, I couldn’t imagine how the sheriff’s family would be fine living in such a place.

St. Augustine

If that weren’t enough, they would also hang the prisoners from the Gallows. About eight men were hung from the Gallows. The conditions at the Jail were also horrible compared to modern standards and most prisoners were used as free farm laborers. The conditions were so bad that each cell consisted of one bucket per cell as the toilet facilities, prisoners would rarely get baths and they would eat animals they wound up catching while working on the fields.

St. Augustine
The Kitchen

While the history and stories are sad, I do love how they’ve gone about doing the tours. Tour guides in character are always a plus and make for an even more fascinating adventure. The Authentic Old Jail also has a tour at night for those wanting to investigate the paranormal activity in the jail.

Gator Bob’s Trading Post

What I love about the Old Town Trolley Main Station is that it is close to the Old Jail as well as other museums and shops. After the Old Jail, we were able to walk around the area checking out the Spice & Tea Exchange store and taking photos around Gator Bob’s Trading Post. If you find yourself in need of a snack, Gator Bob’s Trading Post is a good spot for that.

You can also check out the Oldest Store Museum and the St. Augustine History Museum. We opted out of going to those two museums as we were really wanting to spend time at our next stop.

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Ponce de Leon’s Fountain of Youth Archaeological Park

Rather than taking the trolley to the Fountain of Youth, we decided to walk to this beautiful park. It’s a short distance away from the Old Jail and walking the distance allows you to discover other things you might not catch on the trolley such as the lemonade spot across the street from the Archaeological Park. Fountain of Juice not only has lemonade, but they also have fruit smoothies and coffee.

From the outside, Ponce de Leon’s Fountain of Youth Archaeological Park may not seem big, but once we passed the ticketing booth in the park, I was surprised to find such a big area waiting to be explored. As I studied the map, I realized it would take us at least a few hours to get through the whole park and so we began our journey starting at the Fountain of Youth.

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For years, I had envisioned the Fountain of Youth to be a big opening with perhaps a fountain that gave it, its name, but after looking at the Fountain of Youth closely, I was a bit disappointed to find that it wasn’t as I had envisioned. It was still very interesting to see up close and definitely one of the first things you want to see. We did stop by the Discovery Globe and then the Navigator’s Planetarium, where we learned how explorers from the 1400s and 1500s would use celestial navigation to get to their destination.

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We then headed to the Timucua Burials and later spent a couple of minutes exploring the Timucua Village of Seloy. What I loved about the village was that there were guides there that showed us what the day-to-day life of a Timucua was like. They also had canoe displays as the Timucua in this area would travel using canoes.

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While exploring the park, there were a few exhibits around, but we skipped a few to have more time to explore the rest of the park. We did pass the Mission Church of Nombre de Dios, which was quite interesting to see. I had not expected a village or a church in the park, so it was a nice surprise. Before heading to the Founders Riverwalk, we did get to watch the weapons presentation. If you cannot handle loud weapons, I do not recommend the presentation or the canon firing, but both are great to watch.

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Then we made our way over to the Riverwalk, where we saw numerous small crabs. It was dry with little water below us, and though it seemed strange, it was nice to see the crabs around. The Riverwalk is 600 feet, so after doing the walk we decided to take a break from walking and enjoyed the Canon Firing Demonstration.

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We did go up the Spanish WatchTower and eventually moved along to see the Chalupa & Astillero boats. Having skipped quite a few of the demonstrations, we still spent about 2-3 hours as there was a lot of ground to cover. You might even feel tempted to skip the gift shop altogether but don’t as you will find some fun souvenirs such as the Fountain of Youth Bottled Water.

Smoked Southern BBQ

Right around the Ponce de Leon’s Fountain of Youth entrance is the Smoked Southern BBQ. If you spent as much time at the park as we did, this is a great spot to visit if you’re looking for some lunch.

St. Augustune

St. Augustine Pirate & Treasure Museum

Once we were out of the Ponce de Leon’s Fountain of Youth Archaeological Park, we headed back to the Old Town Trolley main station to take the trolley. We did not wait long to get on the trolley and we got to see parts of the city as we made our way to the St. Augustine Pirate & Treasure Museum. This is in a good location, close to a lot of other attractions as well as St. George Street.

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When getting our tickets to the museum, we were told of a treasure hunt, where you have to find certain artifacts and write them down on the paper they provide. It was fun looking for the artifacts and also learning more about pirates such as Sir Francis Drake and Robert Searles who frequented the nation’s oldest city and the Spanish fort, the Castillo de San Marcos.

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The inside of the museum is quite impressive and loved how they transported us onto a ship with the decorations placed around the museum. There was also the opportunity to play with a canon (a fake interactive canon). After we spent time looking for the artifacts around the museum for the treasure hunt, we turned in the paper and got a prize. While this is mostly for kids, it’s still quite fun to look for the artifacts and I learned a few things by doing the scavenger hunt as well.

St. George Street

About 3 minutes away on foot from the St. Augustine Pirate & Treasure Museum, St. George Street is one of those streets you do not want to skip out on. This street is full of restaurants, shops, and many other attractions to check out. While we did not spend time in St. George Street due to having been there many, many times before, it was still awesome to see how many people were enjoying what this popular street has to offer.

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Old Town Trolley

After taking a few photos of the area, we headed back to the Old Town Trolley stop, where a trolley picked us up within two minutes of waiting. Once we were on the Old Town Trolley, we decided to take the full 90-minute tour without getting off at any of the stops. The conductor shared the history of the city as well as some historical facts about the buildings and neighborhoods.

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There are 22 stops on the tour, and each stop is at one of the attractions or near a few attractions. On the tour, we saw The Old Senator, the Shrine of Our Lady of La Leche, Whetstone Chocolates of St. Augustine, San Sebastian Winery, St. Augustine Distillery, Villa Zorayda Museum, and many other attractions. By the time the tour ended dropping us off at our stop, which was the Old Town Trolley Main Station, It was already nighttime, which meant it was time to go home.

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The beauty about living an hour and a half away from St. Augustine is that my partner and I get to go as often as we’d like. Aside from that, we were able to fit so much into our one-day itinerary and still make it back home before 10 P.M. I know not many have that convenience, but if you are able to go to St. Augustine for one day, then take advantage of it and explore the beauty that is St. Augustine.

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About Me

About Me


Hola! I'm Hanny and I have been traveling since the age of three. Although, I grew up traveling, it wasn't until 2013, when I decided to start a blog. Read More

xoxo Hanny

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