St. Augustine – Why Is the Oldest City in the USA So Amazing?

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Did you know that the oldest city in the USA is St. Augustine, Florida? I will be completely honest and say that I had no idea. St. Augustine is famous in the world of golf given that it is home to the iconic World Golf Hall of Fame museum which inducts golfing legends but when it comes to American history, I had no clue that this city in north-east Florida was so iconic.

world golf hall of fame

In fact, I  still can’t believe it because when you think about American history, you normally associate the early colonies in states like Virginia and Massachusetts rather than Florida. But heading to Jacksonville on our July 4th weekend road trip, we realized that this was the perfect time to explore St. Augustine and understand the history behind the city that has recently celebrated its 450th birthday (September 2015).

St. Augustine – Oldest City in the USA?

Let’s take a step back in time to look at the history of America.

The Roanoke colony was established in 1585, Jamestown in 1607. The pilgrims landed at Plymouth Rock in 1620.

The above quote highlights what many believe to be three of the most iconic dates in American history. However, where does St. Augustine fit into this historical timeline? The first permanent settlement dates back to 1565 when the Spanish explorer, Don Pedro Menendez de Aviles, landed ashore in Florida and named the location St. Augustine after the patron saint of brewers.

oldest city in the usa

The history of St. Augustine never receives the same attention as the locations mentioned above given that the narrative generally dates back to the English story of Jamestown and the pilgrims.

st augustine oldest city in the usa

However, the hope is that more people will realize that St. Augustine deservedly sits at the top of the hierarchy when it comes to American history and after exploring this beautiful Florida destination, the city is certainly doing all the right things to attract more folks to this part of the country.

Downtown Historic District

As we entered the city limits of the oldest city in the USA, we immediately realized that St. Augustine was a city to experience either on foot or taking the quirky trolley that navigates visitors around.

oldest city in the usa

We parked in the garage directly behind the St. Augustine & St. Johns County Visitor’s Information Center. Parking is only $12 for the day which I thought was pretty reasonable, especially given you could spend all day exploring this historic downtown area.

st. augustine florida

We spent some time inside the Visitor Center gathering some additional information and a handy map of the downtown area. After only a few minutes of walking around, the weather took a turn for the worse and we encountered a typical Florida summer storm that lasted for quite some time.

st. augustine florida

Fortunately, we had umbrellas and headed into a quirky undercover neighborhood at the start of St. George Street. A variety of stores grabbed our attention, not only because of the weather and our desire to stay dry indoors but also because of their bizarre yet attractive decor and merchandise.

black parrot candy shop

The Black Parrot Candy Shop immediately pulled us through the door, primarily because of the nostalgic candy available and refreshing selection of frozen drinks. Don’t worry, if you don’t have a particularly sweet tooth, this is also home to a wide selection of barbecue and hot sauces that you can sample. Beware some of the hotter alternatives because they are pretty spicy!

oldest city in the usa

St. George Street – Heart of St. Augustine

Much of downtown St. Augustine is located along St. George Street, a pedestrian only zone where no vehicles are allowed. From boutique souvenir shops to local restaurants, there are plenty of attractions here to capture your attention.

st george street st augustine

Located on the corner of St. George and Tolomato Street is an iconic construction in the city of St. Augustine.  The Oldest Wooden School House dates back to the early 18th century though an exact date of construction is unknown.

oldest wooden school house st augustine

Take some time to admire how this red cedar wooden construction has served the test of time thanks to the preservation of the local government.

st. augustine florida

As we continued walking along St. George Street, it was impossible to avoid noticing the Spanish inspired constructions along with the vibrant colors typical of a Spanish neighborhood. There are a few spots along here that reminded me of our experiences in Barcelona as we explored some of Antoni Gaudi’s famous work.

casa rodriguez st. augustine

Even jewelry stores are located in buildings such as Casa Rodriguez, certainly not an architectural design that you would associate with a typical Kays or Zales in cities around the country.

oldest city in the usa

Another interesting aspect of St. George Street is how many of these historic buildings have been renovated to create indoor malls with a variety of small stores offering local merchandise and souvenirs. Take some time to visit St. George’s Row and The Spanish Plaza and although you may not find anything worth buying, it’s a pretty cool experience to wander through and check out everything St. Augustine has to offer.

Best Restaurants

Rather than debating over where the best restaurants are located in St. Augustine, I am just going to share our personal experience. After researching several spots, we decided to visit The Prince of Wales, a British pub located on the corner of Spanish Street and Cuna Street.

prince of wales st. augustine

When you think of stereotypical British pubs, the outside of the Prince of Wales is anything but a typical reflection. However, this quaint building certainly grabbed our attention and we headed inside to sample some fine British cuisine. We didn’t leave disappointed! The interior of this pub is everything typical of what you associate with England.

oldest city in the usa

From the infamous “British police bobby helmet” that was on the wall to the malt vinegar and HP sauce on every table, it certainly made me feel right at home. The menu offers a variety of options at very reasonable prices, though I went for the ‘small’ Fish and Chips and Heather ordered a Beef & Guinness Pie with mashed potatoes and vegetables.

fish and chips in st. augustine

Our friendly Scottish waitress was always on hand to refill our drinks (not something that you would normally encounter in England given there are no free refills) and we didn’t have to wait very long for our food.

beef and guinness pie

We actually shared both dishes though Heather’s meal was a little on the cold side. Despite this, we really enjoyed our dining experience and this gave us enough sustenance to continue our journey exploring St. Augustine.

kilwins st. augustine

After enjoying your main meal, take a trip to Kilwin’s and enjoy one of their famous caramel apples or perhaps sample their decadent ice cream selection.

kilwins st. augustine

Cathedral Basilica of St. Augustine

If you are looking for iconic focal points throughout St. Augustine, well there are plenty of them. We mentioned the Oldest Schoolhouse earlier but a short walk down St. George Street from here will lead you to the site of the Cathedral Basilica of St. Augustine. This historic cathedral has played an integral role in the history and development of the city and was first constructed in the late 18th century.

cathedral basilica of st. augustine

However, the history of this cathedral dates back to when the Spanish first found St. Augustine in 1565. It is the oldest church in the state of Florida and offers a typical architectural construction of neoclassical and Spanish mission design. If you are familiar with the San Antonio Mission Trail, I am sure you will spot a few key features here that remind you of this design.

basilica of st. augustine

Castillo De San Marcos National Monument

If you are looking for the most iconic landmark in St. Augustine related to the history of the United States, look no further than the Castillo De San Marcos national monument.

castillo de san marcos

Located in the north part of the city, this landmark symbolizes the clashes of cultures that took place here. The cultural influences on St. Augustine are apparent throughout the city but none more so that at this historic monument.

castillo de san marcos

Much of the original architecture has been preserved to this day at the Castillo De San Marcos and it is a perfect example of a bastion system of fortification. It reminded me of our experience at the Historic Fort Morgan site in Gulf Shores, Alabama which has the same type of fortified remnants that visitors can explore.

castillo de san marcos in st. augustine


If you want to visit the oldest city in the USA and learn about the rich history there, then taking a trip to St. Augustine will certainly intrigue you. Although we only spent an afternoon wandering around the historic colonial quarters, it was enough to give us a sneak preview of everything St. Augustine has to offer.

The sense of European heritage is clearly apparent with the vibrant architecture and presence of various British restaurants. With St. Augustine being just a short drive from Jacksonville, it’s inevitable that if you are visiting North-East Florida you will want to take some time to visit.

Have you visited St. Augustine, Florida? Do you prefer exploring historic American locations vs. modern destinations around the country?

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Chris Boothman
Chris Boothman is the co-founder of A Brit and A Southerner. Born near Manchester, England, Chris moved to USA in 2006 where he soon after met his wife and travel partner in crime, Heather. They have since embarked on an amazing journey of travel as they challenge others to follow in their paths of working full-time but also being able to travel frequently! If you have any questions or comments, please feel free to contact Chris at [email protected]


  1. This is a great article and I am proud to say that my mom and her husband own the Black Parrot Candy Shops.
    I have been blessed with being able to visit St. Augustine and it is magnificent.
    I can’t wait to go back and see more and enjoy more of the history behind this beautiful place.


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