A Weekend in Saint Augustine: The City, the History, and the Beach

Saint Augustine is somewhere we have always wanted to visit, but it was never convenient. Jacksonville is the nearest major airport and while it may be growing, it certainly is not a major hub. Orlando may make the most sense, being about two hours south. Regardless, we found ourselves visiting friends who are temporarily living in Jacksonville, so Saint Augustine was a great weekend plan. I am writing this from the hotel as the trip comes to an end. Let me give you a little background on the city, places to stay, where to maybe avoid, and of course where to eat.

Saint Augustine

Founded in 1565 by Spanish explorer Pedro Menéndez de Avilés, Saint Augustine is the oldest continuously occupied European-established settlement in the continental United States. With the beautiful architecture, the layout of the roads, and the streets themselves, it is clear that the city is very old. That said, according to the city’s website, only the Castillo de San Marcos, built to defend Florida and the Atlantic trade route, is architecture from that era. The rest of the city was built after the British invaded in 1702.

The city is also home to a bit of history tied to the Underground Railroad. The Spanish had a very different view on slavery, not all positive, but that is a conversation for another time. The city became an important part of the Underground Railroad, with their own agenda in mind of course. Escaped slaves were granted their freedom by the Spanish Governor if they declared allegiance to the King of Spain and the Catholic Church.

The history continues with impactful periods including the U.S. Civil War, both World Wars, and so on. As you may know, cultural travel is at the forefront of my writing, and Saint Augustine did not disappoint. It focuses on a part of history that most of America is not familiar with, simply because it predates America itself. Most of the history here predates what you will see in Boston, Philadelphia, or other historic northeastern American Colonial cities.

Visiting and Staying

The Beach

Saint Augustine has two areas that attract visitors, the city itself and Saint Augustine Beach. I will talk about both. We stayed at the beach at the Tapestry Collection by Hilton, called Castillo Real St. Augustine Beach Resort. Calling it a resort is a stretch. While it may technically meet the criteria of a resort, it was more of a boutique hotel with some good amenities. That said, that was a win for us as we are not big on resorts for the most part.

The area around the hotel was, well, a bit underwhelming. There are a handful of restaurants up and down A1A Beach Boulevard, the main road through the island. Each one was packed, loud, with long waits, and there did not appear to be any other options. It was your typical beach town, with beach-style restaurants and bars. That said, there was not much of an option to grab a drink other than those same packed restaurants. Our hotel had a nice but very small bar. We ended up walking about ten minutes down the street to the bar inside the Embassy Suites. We were very glad we did, because while it was also very busy, it was massive, with a large outdoor area and plenty of places to sit and relax.

The beach itself, I must say, was a win. It was wide open with plenty of places to set up. It felt clean and open. I did not see any beach chair or umbrella rentals, so keep that in mind. That could have simply been where we were, or perhaps March is too early for them to set up on the beach.

The City Itself

This is the real Saint Augustine, and if you are looking to visit the area for everything or anything I mentioned in the opening of this article, this is where you need to focus your time. The streets are cobblestone and the buildings are beautiful. I will say, there are parts of the city, such as parts of St. George Street, that can feel overwhelmingly touristy. However, you can easily escape that and find yourself right back in a relaxing, historic setting with quaint restaurants and shops. We ate at the Forgotten Tonic on Aviles Street, and it was excellent and affordable. I had a fish sandwich served on ciabatta bread with the fish blackened. We walked around some more and had coffee at Southern Grounds & Co. before heading back to the beach.

Summary

It was a good weekend. Next time, we would stay downtown and drive to the beach for the day, not the opposite. That said, no regrets. The city simply has so much more to offer than the beach area. The city does not feel like Florida, it does not feel like America for that matter. I highly recommend it!

Have you been? Comment your thoughts!

The featured image, showing Flagler College as a sketch, was taken by Jay and then transformed into a sketch with the assistance of AI. We are sharing this as part of our commitment to writing integrity.

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