January 8, 2025

We took an unexpected direction heading south to Florida last winter. This was our first trip towing the RV out of our home state to what would be our winter location for an extended period of time. When our path changed for Florida, I knew of just the place I wanted to land. I was drawn to Saint Augustine by descriptions I had heard over time, which summed up the scene as having stunning architecture and a rich history that complements all aspects of the city. The stories were true. Walking around town, Saint Augustine lives up to its word as the Nation's Oldest City. After three months exploring the area, I feel confident sharing some of my favorite spots that are sure to show you a more historic and natural side of Florida!

A little background:

Saint Augustine has a diverse history and has gone through many phases over time. While walking around the old town, you’ll notice a few flags represented on information plaques sharing bits of knowledge about the past. St. Augustine was founded in 1565 and was ruled for nearly two hundred years by the Spanish, then by the British for twenty more. The Spanish then had control again before Spain ceded Florida to the United States in 1821 (City of St. Augustine).

The land where St. Augustine now stands was stolen from the Florida Timucua Native people. The Timucua grew much of their food in planned crops primarily consisting of pumpkins, cucumbers, peas, gourds, maize, and beans. They gathered food such as berries and nuts and remained in relatively the same area year-round. A main protein source for the Timucua people were fish and other seafood such as oysters. Although not much is known about the religious practices of the Timucua people, it is known that they worshiped the sun and the moon. Deadly diseases brought by European colonizers, such as smallpox, killed many Timucua and impacted their numbers greatly. In the 1500s before European arrival, the Timucua population was about 200,000 individuals, but by the 1800s, only a few remained, with survivors joining other tribes like the Seminole and Muscogee Creek (National Park Service).

Upon arriving in Saint Augustine, you’ll see two names more than any others: Ponce de León and Henry Flagler. 

Juan Ponce de León was a Spanish Explorer known for leading the first successful European expeditions to Puerto Rico in 1508 and Florida in 1513. Ponce de León originally landed south of Saint Augustine and traveled down the coast. Legend says that he was searching for the Fountain of Youth. The Fountain of Youth is a mythical spring that is said to restore the youthfulness of those who bathes or drinks from the water. If I were searching for a spring with magic healing powers, I'd head to Florida too! To learn more about the Florida Springs, check out my Beginner’s Guide! 

Henry Flagler was an American industrialist and entrepreneur. His many business ventures led Flagler eventually to a co-founding partnership in the company Standard Oil with John D. Rockefeller. Standard Oil became the leader in American oil refining at the time. However, after a honeymoon trip to Saint Augustine in 1883, Flagler set his eyes and investments on Florida. He built the iconic 540-room Hotel Ponce de Leon in St. Augustine, now part of Flagler College, and continued to expand with more coastal hotels. He then began to connect his hotel cities with a train track from Jacksonville to the Florida Keys including 156 miles of track over water (Flagler Museum). The transportation infrastructure, tourism, and agricultural industries supported by Flagler forever changed the economic outlook of Florida. 

Now that you’ve done your St. Augustine history readings, you can truly grasp the significance of this city for yourself when you visit! I came to Saint Augustine for the architecture and to learn the history. I also came to this city to be in a less populated area of the state compared to where many snowbirds usually go: southwest Florida. The snowbird season in Florida is November through April, give or take one month. Although I can not find any definitive numbers on the amount of snowbirds coming to Florida every winter, there’s no denying the economy and roads see a difference and the locals take notice. Saint Augustine traffic can be busy but after also driving through Orlando and the Tampa area, I stopped complaining. To beat the crowds, this location was the right choice. I definitely feel like I got all that I came for and so much more from our time in Saint Augustine. 

Besides being rich in history, another lesser known aspect about Saint Augustine is that there is incredible access to nature and trails. We were so pleasantly surprised with the availability of parks and places to run, hike and bike. We hit a new trail or park nearly every week just to seek out the best spots and views! In this blog, I share a total of fifteen trails, conservation areas, parks and beaches to help you get outside and into the lush Saw Palmettos or onto the beach! I am also sharing two easy day trips from Saint Augustine that are sure to get you exploring the natural beauty just beyond St. Johns County.

Let’s start with food! I imagined myself coming to Florida and eating fish by the ocean and trying all the local cuisine I could. That’s exactly how it went! Here are the top places we dined at:

What ended up being my favorite part about Saint Augustine was all the nature trails we visited! We were able to bike and jog a lot of places in three months. These are some outdoor suggestions:

Despite being 20 minutes from the ocean, we did not visit nearly as much as we should have! However, we managed to find some enjoyable and accessible spots to go when we wanted to! One thing we loved is that the beaches were never crowded or busy like other Florida beaches can be! Here are our favorite beaches:

Another cherished aspect of Saint Augustine is seeing the history and how it has become part of the city today. Here are some of the most memorable bits of historic St. Augustine:

These are three additional places I also recommend visiting if you’re interested:

Here are our two favorite day trips from St. Augustine that I highly recommend if you have time:

I hope, if you’re searching for Saint Augustine recommendations, you found this information helpful in your planning! There is so much to experience in and around this city! With all the food and trails we tried, it is easy to see why I miss St. Aug and why it made such a smart location to start our RVing journey! However, the unique historic charm and architectural elegance of Saint Augustine cannot be fully captured in this blog and is worth experiencing firsthand! Whether you find yourself indulging in nature or the local cuisine or both, there’s plenty of options to choose from when you visit Saint Augustine! 

Check out my full collection of recommendations on the map below: