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Saint Augustine: The Oldest City in the US is in Florida.

Updated: Jun 28, 2021


I have to tell you. The first time I visited Saint Augustine, I was not impressed at all. Everything seemed fake. The beautifully-flat landscape of the oldest town in America contrasted with the phony historical sites and ubiquitous touristy stores. Yeah, I get it. Locals had to find a way to survive and milk the Spanish heritage of the city, but to say I was disappointed was a euphemism.


For reasons I'm still not sure, I decided to give it another try and visit this historic town once again. Maybe I went to the wrong places or there was something I wasn't getting about Saint Augustine. However, this time, I invited a dear friend of mine, a historian by the name of Robert Gold whose specialty is, you guessed it, Saint Augustine! And, just like that, I was hooked.


Saint Augustine Castillo San Marcos Matanzas River
Castillo de San Marcos on left and Matanzas River on right.

Saint Augustine became a weekend getaway. A place to spend the day and drive back home through the scenic A1A, a beautiful coastal road where you have breathtaking views of the Atlantic Ocean contrasting with the light brown, slightly-shelly sand of northeast Florida. At the time, I was living in Jacksonville and a quick thirty-minute drive would get me to the Spanish town of the conquistadors. A1A connects most of the oceanfront towns from Key West to Fernandina Beach, near the Georgia border, and my drive would start in Jax beach (as locals call Jacksonville), passing through Ponte Vedra, and ending in Vilano, where I would make a right turn to cross the bridge to Saint Augustine.


Ponte Vedra Beach Florida
Ponte Vedra Beach, Florida.

At this point, Saint Augustine was a hit. I would take friends and family to stroll through the cobblestones streets (paved bricks, some say) of the oldest town in America whenever they visited. The more I went there, the better I learned about the broadly-documented history of the city, the right places to go, and the exquisite restaurants. It was as if I were getting local, and I guess friends and family were infected with affection for the city as well.



Flagler College Saint Augustine
Casa Monica Resort

After the scenic drive, I would park near the Castillo de San Marcos and walk down Saint George Street in the direction of possibly the best restaurant in town: Columbia. This Spanish restaurant founded in Ybor city, Florida, grew to six other locations. Columbia is always packed. It is not easy to find a table, nor should it be. The food is delicious, so be sure to make a reservation prior or risk losing some of the best meals you'll ever have. My choice of options were always the same: eating as much as cuban Cuban bread as I could, followed by queso fundido loaded with more cuban bread. Friends and family would always go for the 1905 original salad accompanied by the pitcher-sized sangria. Tinto, of course.




Right after Columbia, I would stroll a bit longer on St. George Street and go grab a fudge at Whetstones chocolates. Plain chocolate was always my choice. Here I must warn you, If you have never had a fudge before, It is sweet. Damn good sweet. I'd grab a bottle of water and then walk from the Castillo until the Bridge of Lyons. The Matanzas River, the same river where the Spaniards arrived in 1565, offers you a magical view of this charming town and a glimpse of the past.


Now getting ready to drive back home, I would always walk pass the Flagler College, a private liberal arts college founded in 1968 and a beacon of history of Saint. Augustine. Before turning it into a college, it used to be a hotel called Ponce de Leon. One in a series of resorts built by Henry Flagler, one of the founders of Standard Oil Company, along the Florida Coast.


On my way back, already driving to Jax, I would sometimes take an alternative route, especially if friends and family were together. Instead of taking A1A, I would drive towards I-95, an interstate highway that links the entire east coast of the US, from Miami till the Canadian border. Before entering the highway, there are two huge plazas filled with outlet stores, the Saint Augustine Outlets. There was no better way to end the day than indulging myself with some shopping spree.



Places I Recommend


  • Columbia Restaurant

  • Whetstone Chocolates

  • Castillo de San Marcos

  • Pizza Time

  • Casa Monica

  • Cutter & Cutter Fine Art



By Rosalvo Gomes

Contact: sourtake@gmail.com

All pictures my own.



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