Bask in the Weirdness that is St. Augustine

Fountain of Youth, St. Augustine Florida

I frankly had no idea why we going to St. Augustine. Scott wanted to visit the World Golf Hall of Fame and play some famous courses in nearby Ponte Vedra, Florida and to make the trip more appealing to this non-golfer he suggested that we could spend some time in St. Augustine. Always willing to experience a new travel spot, I acquiesced, but to what I wasn’t sure.

Here is what I knew about St. Augustine before we left: it is very old and has some sort of Spanish influence. Ta-da! That’s it folks. I suppose I should be ashamed at my dismal knowledge of Florida, nay, American history, but that was the best I could do. As I would soon learn though, St. Augustine is one of the strangest places in the country, if not the planet.

Our first venture into the oldest town in America was a quick drive by, on our way to play putt-putt. (hey, I do have my priorities) During the five minute drive through town though I saw at least 20 trolley tour companies, a neon sign announcing the Fountain of Youth, and enough tourist signs proclaiming to be the “Official Whatnot,” that I knew there was probably no “Official Whatnot“. In that quick drive I seemed to be cast back into the mid-sixties when kitsch and camp ruled the roost of the travel industry and it frankly didn’t bode well for the rest of the trip.

Determined to see as much of the town as possible despite the mind-boggling humidity and scorching temperatures, the next day we set out to give St. Augustine a chance. I’ll detail the specific sights and attractions in future posts, but our experience was indeed a strange one. While on the surface, this ancient town does err on the cheesy side of tourism (imagine everything named some sort of Shoppe), once you spend some time there you see an entirely different side to this strange little place.

St. Augustine, Florida
Downtown St. Augustine

As we were walking through the tourist zone, I began to notice a lot of artists and eclectic looking people milling about, strumming guitars, and in general just hanging out. Then, beside the official tourist stores, there were cute little arts and crafts shops, owned by the artists themselves and equally unique cafes and restaurants lining the street. This I was not expecting. From previous experiences around the world, the touristy areas usually stay touristy and the cool areas want nothing to do with them. Here, in St. Augustine, they exist in what is an incredibly successful state of commercial symbiosis. Like birds on an elephant, the small shops depend on the large tourist types to draw in their customers for them.

What it reminded me of most was New Orleans, which also exists in a permanent state of the strange and sublime. The same characteristics of southern charm and hospitality exist here as well, making such a strange mix of people even possible. The tradition of acceptance and even ambivalence towards the actions of one’s neighbors have made the cities of New Orleans and St. Augustine into the areas of general affirmation that they are today.

The rest of our brief stay in St. Augustine was a wonderful experience with strange new discoveries almost literally at every turn. From turn of the century, robber-baron hotels to a vibrant artists colony, the city never failed to surprise.

By the end of our stay, it was clear that my initial skepticism about the city was unfounded. Yes there are campy, corny attractions in town, but that simply adds to its charm. In order to truly enjoy this magnificent city, you have to leave your preconceptions at the door and just let yourself enjoy it as it was meant to be enjoyed – by living it.

By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer.

3 thoughts on “Bask in the Weirdness that is St. Augustine”

  1. St. Augustine is a great place to take a break. Yes, the downtown area there is a bit kitschy but there are plenty of diamonds in the rough as well as you discovered. My personal favorite is the kite store on St. George street.

    Head over the Bridge of Lions and out into the beaches you’ll find huge swaths of sand that are relatively uncrowded. It is a great beach – one of my favorites.

    I’ll be back down there in October again and cannot wait!

  2. I know exactly as much as you knew about St. Augustine, Matt. :-) Yet, I’ve heard it’s beautiful, and I’d really like to visit. I mean, who can resist a visit to the Fountain of Youth?

    1. it really is a cool place. We ate at a great little cafe that I’ll write about soon that had the best vibe. It was lunch, but there was live music and awesome people milling about. I’d definitely go back.

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