St Augustine: America's Oldest City

~Edd

During the sad sack that was my ill-fated trip to Pensacola, Riss was already planning our next stop. To get to Pensacola, FL from Wilmington, NC you have two options: Atlanta or Jacksonville, FL. On the way down we took Atlanta, and so we chose the Jacksonville route for our glorious return. For Riss’s honeymoon, her and Rob had gone to St. Augustine, which is a scant 30 miles south of—you guessed it—Jacksonville. Riss was pretty sure that I’d love the place, too, so she was determined to take me. Since I had turned down the job, was still unemployed, and honestly could use some cheering up, I agreed.

In order to maximize our St. Augustine time, we left Pensacola at 3AM after a super solid nap. On the way, we stopped at an all-night Whataburger. In college, I had a friend from south Georgia that told tales of Whataburger. When passing the sign, I remembered these stories, and knew that my time had come. For anyone that has never had or heard of Whataburger, do yourself a favor and go. I had a chorizo cheeseburger, Riss had a pretty dope patty melt, and they were both glorious!

We got into St Augustine at about 9:30AM. Sadly, hotel check-ins aren’t until 2PM, but the Old Town Trolley Tours start running at 9! Old Town runs a hop on/hop off route around the town, with new trolleys coming by every 15 minutes. We rode the entire route first, then hopped off at some of the stops we enjoyed the most, including a *FREE* tour and tasting at St Augustine Distillery. We also ate lunch at Prohibition Kitchen, a speak-easy style place with a fantastic grilled cheese and even better milkshakes (pro tip: get the
one with the booze.)

Stuffed and entertained, it was finally time to check into our hotel: The Ponce. They’re currently renovating, but that didn’t affect the room or the view, and it cut the rate way down. Midday naps are boss!

We woke up right before sundown. Riss wanted to see the Nights of Lights that Old Town does around Christmas. According to National Geographic, St. Augustine is one of the top 10 places to see holiday lights in the whole damn world. Source.  After doing the tour, I can see why. They even gave us glasses that refract the light and make the individual lights look like snowflakes. I’m a self-
proclaimed Grinch. Christmas isn’t really my bag, but sitting in the trolley, in 60-degree weather, seeing this already beautiful city lit up, that shit was magical. I’d say my heart grew three sizes that day, but I’m still a right bastard, so let’s not get ahead of ourselves. 

After getting off the light tour, we walked the 4 blocks back to the distillery. Upstairs from the distillery is the Ice Plant Bar and restaurant. We sat next to this incredibly memorable guy and his incredibly forgettable girlfriend. She was not impressed with his joie de vivre. We were impressed, both with his lust for life AND with the food, all farm-to-table super bourgeois and delicious. The cocktails are made with the liquor from the distillery. All-in-all, this is a good place and a great atmosphere.


We took an uber back to the hotel, slept well, and left the next morning after check-out. It was right at 24 hours that we spent in St Augustine, but the city left a very positive and lasting impression on me. I’ll definitely be back. I may even like Christmas lights, but just a little.