Live a great story. That’s my motto for 2023; to have a great story to tell about how I spent the 365 days of 2023. And how can I tell a great story without a lot of travel? Back in 2018, I did a “Year of Travel”, where I traveled somewhere every month of the year. I’m planning to make 2023 another Year of Travel and my first stop was none other than America’s oldest city, St. Augustine, Florida.

I arrived late on Friday night after having to change planes at LaGuardia, where I got to enjoy a burger and fries at Shake Shack between flights. It is about an hour’s drive from the Jacksonville airport to St. Augustine and by the time I got to my room, it was almost midnight. I fell into a deep, but not nearly long enough sleep, and soon it was time to get out and explore.
I felt absolutely ridiculous packing my heavy winter coat into my suitcase for this trip. But the joke’s on anyone who thinks it doesn’t get cold in Florida. It was 39 degrees on Saturday morning and I felt much better about my decision to bring it while everyone else was walking around and shivering in the cold. As I walked from my hotel to my breakfast destination, I got my first views of the historic city center of St. Augustine. Since the city was first founded in 1565, there is a lot of historic charm in the Old Town.


My breakfast destination on Saturday was the Maple Street Biscuit Company. Obviously, I needed a strong mimosa (strawberry/blueberry) to accompany my biscuits and gravy with a side of cajun potatoes. If you’re looking for flavor, this place delivers it in spades. The flaky biscuits and perfectly cooked eggs were a nice contrast to the spicy sausage gravy, which left my mouth feeling the pleasant kick long after I finished my last bite.

I mentioned that 2023 is going to be a Year of Travel, so imagine my surprise when the sign above the cash register asked, “What is one place you want to travel to in 2023?”. They ask you that question when you order and your answer is what they call out when your order is ready. How cool is that? As I was eating, I heard everything from Miami to Jamaica to Greece being called out. (I can’t tell you what they called out for my order because that would give away the epic trip I’m planning for later this year!)
After my delicious breakfast and morning libation, I set off to walk through the historic area en route to my morning tour of historic Flagler College. Flagler College was founded in 1968, but its history is actually much older than that. Originally built by Henry Flagler as the Ponce de Leon Hotel in 1888, it served as a popular winter hotel for those escaping the cold northern winters before transforming into the liberal arts College it is today. Imagine being a college student eating dinner surrounded by 79 Tiffany windows!


Next up was a stop at Henry Flagler’s other St. Augustine hotel, the Alcazar Hotel, part of which is now the Lightner Museum. The museum has an eclectic collection of artifacts from snake skins and colored sand to cut glass and Victorian artwork, all collected by Otto Lightner. It was interesting, but I was tired. A short afternoon nap was in order before I got my second wind for the day.

Did you know that St. Augustine is home to the largest masonry fort in the United States? Castillo de San Marcos was originally built as a Spanish fortification to protect against European invasions. It has since had a long history, having been held by the British, the Spanish again, and the Confederates, before ultimately belonging to the United States of America. Today, the fort itself holds exhibits about its history, and a group of costumed volunteers demonstrate muskets and/or the cannons several times a day. I was fortunate to see the last cannon demonstration of the day during my visit.



You’d think finding a dinner spot would be easy, but it was not. The historic area was wall to wall people and all of the restaurants were crowded. I decided to head back in the direction of my hotel and ended up with a nice window table at The Raintree, just a block away from the hotel. A nice sparkling wine cocktail and pork schnitzel with lemon butter sauce made for a perfect dinner. Though I was tempted by the dessert menu, I had something even better waiting for me. I had stopped at the Savannah Sweets candy shop while I was walking around and picked up a salted caramel praline which was a deliciously decadent evening treat.


Sunday morning found me up well before dawn and driving to the beach for sunrise. Since I wasn’t sure about the beach access and parking situation, I arrived at the St. Johns County Pier about a half hour before sunrise and had time for a brisk walk before the sun came up. It was (again) only in the upper 30s and I was (again) thankful that I brought my winter coat with me.



After sunrise I hightailed it up the street to the A1A Beachside Diner for some sustenance in the form of eggs Benedict and hash browns for breakfast. The hollandaise sauce had a very tangy lemon flavor; definitely a delicious start to the day!


Then it was off to visit another historic fort, this one requiring a little more effort to get to. Fort Matanzas is located across the Matanzas River on Rattlesnake Island and requires taking a (free) National Park Service ferry across the river for a ranger-guided tour. The fort is pretty small, as only small vessels could navigate the relatively shallow water of the river. Groups of 7 soldiers would spend 30 days at a time at the fort. You can visit all three levels of the fort during the 25 minutes or so on the island.


After the tour, a volunteer naturalist was leading a short nature walk. I joined that and learned about whales, turtles, beach erosion, and even fiddler crabs for about half an hour. Then I enjoyed a walk along the nature boardwalk before heading back to St. Augustine.

I spent the afternoon indulging in both chocolate and wine. I started with a guided chocolate tasting tour at Whetstone Chocolates where, decked out in my hairnet, I sampled six different chocolates while learning about the whole chocolate making process. It was fascinating and something I knew little about beforehand. Afterwards, I headed to nearby San Sebastian Winery where I sampled six different wines, none of which were as good as the chocolate.


Dinner on Sunday was at Pizzalley’s Chianti Room, where I sat at an outdoor table under the heater while enjoying a Buffalo chicken pizza. While good, I didn’t taste even a hint of Buffalo sauce and left a little disappointed.
I did some souvenir shopping along St. George Street on the way back to my hotel. As I was coming out of one shop, everyone on the street had their eyes turned toward the sky – apparently, I had just missed seeing the Space X Falcon Heavy rocket launch from Cape Canaveral, but did manage to see the booster rockets come off and get a picture of the contrail.


I was up early again on Monday morning to take one final (cold) walk around the city at sunrise. As I was leaving the city, I stopped at Metro Diner for a yummy croissant French toast and then started making my way back to Jacksonville. I decided to take the scenic route up the coast through Vilano Beach, Ponte Vedra Beach and Jacksonville Beach before heading to the airport. My flight was delayed about 45 minutes, but I still made it home in time to relax a bit before heading back to reality tomorrow.





While St. Augustine isn’t my favorite southern city (that superlative is reserved for Charleston, South Carolina), there was a lot to do and I’m glad I spent a few days checking it out and seeing the sights. It was a good start to my Year of Travel and I’m looking forward to making the rest of 2023 a great story.
