This post may contain affiliate links which means I may receive a commission for purchases made through links. I will only recommend products that I have personally used! Learn more on my Privacy Policy page.
St Augustine – The Oldest City in America
St. Augustine is my favorite city in the entire United States. It’s so charming you might forget what country you’re in as it looks just like an old, beautiful European city. A city so coveted it was fought over for hundreds of years, eventually becoming part of the U.S. in 1821.
St. Augustine is not only spectacular and adorable but also the oldest city in American history, settled in 1565. I have zero recollection of learning about St. Augustine in school. Truly, I didn’t even learn of its importance until I was working on my Master’s in American History. The Spanish settled St. Augustine at least forty years before the Jamestown settlement.
St. Augustine began its colonial history with Juan Ponce de Leon’s arrival to what was known as Timucua Village in 1513. Pedro Menéndez de Avilés would establish the Colony of St. Augustine for Spain in 1565. Henry Flagler (Standard Oil Partner of John D. Rockefeller) is responsible for developing St. Augustine to look like an old European city in the late 1800s, making it an old money winter vacation destination. (1) This city has some serious history and beauty you won’t want to miss visiting. There is so much to do and see; one visit will not be enough. I promise you will fall in love, so let’s get started!
Driving on the A1A – To St Augustine
Our drive started in Maryland as we headed south to Florida. This would be our first time on the historical A1A; the highway which winds through all the coastal towns from Fernandina Beach to Key West.
Our all time favorite travel book is “The Most Scenic Drives in America” as it gives you the best scenic routes to take and where you should stop along the way. I cannot recommend this book enough for anyone who loves road trips or has a recreational vehicle. Check out it out here: “The Most Scenic Drives in America”
Anastasia Island
St. Augustine Beach is located on Anastasia Island, just ten minutes away from the city. We took a trip at the end of February and chose to stay on the Island, mixing together a few beach days with sightseeing days. The weather was absolutely glorious, with 75 degrees and the perfect amount of wind all the time.
We stayed at two different hotels across the street from the beach. One we were highly impressed with and will stay at again is the Courtyard by Marriott St. Augustine Beach. I also recommend staying at Embassy Suites By Hilton St Augustine Beach-Oceanfront Resort, as we spent some time at it’s restaurant and poolside and will stay here next time.
Want more places to stay in St. Augustine?
I would also highly recommend the two hotels below:
Casa Monica Resort & Spa, Autograph Collection or the Hilton St. Augustine Historic Bayfront
Local Flavors you Must Try on Anastasia Island
Mango Mango’s Caribbean Grill and Bar – Mango’s famous Corn Cakes – Oh my goodness, they are so delicious!
Sunset Grille – We sat on the second floor, which has semi-outdoor seating, and it was the best place to watch the sunset with a view of the Atlantic Ocean.
The Kookaburra—Every morning I would walk to the cutest coffee shop to grab a cup of joe. The kookaburra is a local favorite and quickly became my guilty pleasure as well. I would grab my coffee every morning and then take a relaxing stroll on the beach.
Exploring Historic St. Augustine
St. Augustine is one of those towns you will enjoy walking through, as it is aesthetically pleasing. As I said, it feels like you are in an old European city, which is understandable since this town was built almost five hundred years ago. We spent our days moseying through the shops and checking out historic sites. There are many amazing things to do, whether it is your first or tenth visit.
Check out this really cool tour while in St. Augustine: Step back in time with pastime private historical tours
— Photo by VIAVAL
Jump on the Trolley
The Old Town Trolley is the best way to get around historic St. Augustine. My family had so much fun jumping on and off all day. The trolley is not free, so you will need to buy a ticket, but it is totally worth it and you can check out Old Town Trolley Tours Here. You also get a little bit of a history tour while you are riding.
Castillo de San Marcos
Castillo de San Marcos is the oldest Fort built in the United States. It was built between 1672 and 1695 to protect the city of St. Augustine from the British. The Fort would serve as a prison for Native Americans during the Seminole Wars and also a prison for Confederate Soldiers during the Civil War. It is now a U.S. National Monument managed by the National Park Service. Check out the Castillo de San Marcos historical tours.
St. Augustine Pirate Museum
St. Augustine celebrates pirates several times throughout the year, which may lead you to believe there is a rich history of pirates here. (In reality, there was only one pirate raid…) Sir Francis Drake, a privateer for the British Empire, was commissioned to plunder and attack the Spanish Colony. Drake was highly successful in his raid, but there were no other pirate attacks, and they also didn’t hang out in St. Augustine’s ports. (1)
Despite this scant brush with piracy, St. Augustine has the best pirate museum I have ever been to by far. Here’s an anecdotal testament to it’s greatness: at first, my husband was not thrilled to check it out. Like I said however, this is the most excellent pirate museum we have ever been to—so much so that afterwards he wanted to go back again the next day! (Have you ever been to a museum you wanted to see twice in two days!?) Their collection is impressive and the presentation is engaging, even better than the museum at the pirate capital of the world in Nassau, Bahamas.
Ripley’s Believe it or Not Museum Castle (The Original)
I am not a big Ripley’s museum fan, but this is where he housed his first collections which are still there on display. The castle has quite the history in itself and is believed to be haunted. It was originally built by one of the original Standard Oil partners, William G. Warden. My whole family enjoyed this museum and I would highly recommend a visit.
Ponce de Leon’s Fountain of Youth Archaeological Park
The myth of Ponce de Leon’s search for the famous Fountain of Youth is nothing more than a long-continuing tall tale that continues to be believed. Historians have been unable to find any record of Ponce de Leon ever mentioning or writing about the Fountain. In fact, the Fountain of Youth only began to become popularly associated with Ponce De Leon’s name ten years after he passed! (2)
A woman by the name of Dr. Luella MacConnell purchased what is now known as the Ponce De Leon Fountain of Youth Archeological Park in 1900. She found several springs on the property and began marketing it as the Fountain of Youth. Wealthy vacationers would come from afar to drink of its promise to make them youthful.
The property was then purchased by Walter Fraser who recognized its historical value. The Ponce De Leon Archeological Park even contains the original settlement of St. Augustine as well as some Native cultural heritage going back three thousand years. (3)
Original public domain image from Library of Congress
Flagler College
Flagler College was once the old money “Hotel Ponce de Leon” built by Standard Oil Tycoon Henry Flagler. He would discover this beautiful town when his wife’s doctor prescribed that they go South for the winter to make her feel better. While in town during the late 1800s, Flagler stayed in a hotel that he thought could be better. So, he decided to build a Spanish-style luxury hotel, the Hotel Ponce de Leon. As a result, this grand hotel opened its doors 1887 to the wealthy as a winter vacation hotel.
Today, the hotel exists as a Liberal Arts campus called Flagler College. They give historical tours incorporating how the hotel once operated in the late 19th Century. Many famous Presidents stayed in the hotel when it was in operation. By the 1920s as Florida continued to be explored, the hotel became less and less occupied, primarily due to Flagler’s railroad being constructed down to Key West.
The hotel would stay in operation during World War II. Eventually, it would be closed due to the Federal Government taking it over to use as the Coast Guard Reserve Training Center. Then in 1968, the hotel would become what it is today: Flagler College. I highly recommend taking this tour and walking around the college; it is gorgeous.
Flagler also built two other successful hotels, the Alcazar (Now the Lightner Museum) and the Casa Monica Hotel, which is still open today, and the one I mentioned staying at while in St. Augustine above. Make sure you check them out on your next visit.
And Now for your History Deep Dive…
Pedro Menendez de Aviles is not only the founder of the oldest settlement in the United States but also a seriously adventurous badass. He mastered traveling across the Atlantic Ocean- accomplishing the feat approximately fifty times throughout his lifetime. The fastest he accomplished crossing from St. Augustine to the Canary Islands in a small chalupa (small boat) was eighteen days!
The Contract with the Spanish Crown
Menendez de Aviles would sign a contract with the Spanish Crown, allowing him to fund his colony in what is known as present-day St. Augustine. He was granted one month and a half to load ten ships vessels with weapons and supplies to live on. He would employ a total of 500 men alongside him, including sailors, farmers, men of war, clerics, blacksmiths, stone masons, surgeons, and master beer brewers. According to the contract, two hundred men he had to take along had to be family men: they were required to be married and take their wives on the journey too so that they would desire to stay settled in the new colony and not leave in search of a woman elsewhere.
In this contract, the Spanish Crown also required all these people to be religiously clean. Menendez de Aviles knew there was no way he could find that many religiously clean people for this expedition. So, he would convince the Crown that he could wait, but if he did Spain would lose out on claiming this territory. By putting fear into the Monarch, he would convince them to allow him to take a multicultural group of people to settle in this new colony. Approximately thirty percent of the entire colony is not Spanish.
In this contract, he was also required to settle two to three towns in the first year of arriving in St. Augustine and place five hundred slaves to grow sugar cane. Menendez knew he was not going to have slaves grow sugar, so he took the 500 slave licenses that he was granted and sold them in the Caribbean for money.
St. Augustine Colony Survives
In the first three years, he established not three but fifteen towns and made it all the way West to Tennessee in the mid-1500s. As he continues to make his way through North America, he begins to run into Natives who are not happy to meet with him. Due in large part to these conflicts by the end of 1587, only St. Augustine survives. (4)
Sadly it is Ponce de Leon who gets the credit for discovering St. Augustine. However, it is genuinely Menendez de Aviles who is responsible for the beginnings of this beautiful city that we still enjoy today. Henry Flagler would be the next pioneer to architecturally develop St. Augustine. He is responsible for paving the wilderness of Florida with railroads and making it what it is today.
Source:
(1). https://www.britannica.com/place/Saint-Augustine-Florida-United-States
(2). https://myfloridahistory.org/preservation/ponce-de-leon-and-florida%E2%80%99s-fountain-youth
(3). https://www.fountainofyouthflorida.com/history/
