Exploring the Oldest City in America: St. Augustine, FL
Step into the past and visit America's oldest city-- St. Augustine, Florida. Founded in 1565, this coastal town was once a strategic Spanish stronghold, but today, it's a favorite destination for history buffs and beach lovers alike.
My trip to St. Augustine came about thanks to the recommendation from a tour guide in Savannah. They suggested doing the trifecta of southern founding cities: Savannah, Charleston and St. Augustine.
I don't need much nudging to go on a trip, so St. Augustine here we come! This trip was filled with history and relaxing in the sun (shade for me).
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Stays within the Historic District or along the Beach offer best value.
Hyatt Place St. Augustine/ Vilano Beach
Renaissance St. Augustine Historic District
Casa de Solana Bed and Breakfast
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Enjoy southern and Spanish style eats:
Columbia Restaurant
River & Fort Restaurant and Rooftop Lounge
Floridian
Sunday
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Top Activities and Attractions:
Castillo de San Marcos National Monument
Old Town
Fountain of Youth Archaelogical Park
St. George Street
Lighthouse and Maritime Museum
Historic District
Getting Around
The closest major airport to St. Augustine is in Jacksonville, FL. Normally I do not drive on vacation, but as St. Augustine is about an hour away, renting a car is a must.
One thing to note: most hotels in St. Augustine charges for parking or doesn't have lots onsite, especially in the downtown area. If you're staying within the downtown area be prepared to potentially be looking for parking.
We opted to stay on Vilano beach, which was about 10min from the historic district. This hotel had a mandatory $25 valet per day added. At first I wasn't thrilled about it, but it was quite convenient.
St. Augustine is mostly walkable, but keep in mind that the main attractions are in three major areas: Historic District, Old Town and the Shoreline. To make the most of your visit, I highly suggest getting a hop on hop off tour pass. You'll see stalls all over the city selling tickets, and they also offer bundle packages that grant access to several of the main attractions.
This was the easiest way to traverse the city, especially in the heat of August. If tours aren't your thing, they have your usual rideshare options and peddy cabs.
Where to Stay
When planning your stay in St. Augustine, your choice of accommodations depends on your focus. If you want to immerse in the heart of the city, downtown is the way to go. St. Augustine takes pride in maintaining support for small businesses, so downtown you won't see a ton of your usual big name hotels. Instead, there are charming bed and breakfasts all around the city -- perfect for those looking to soak in the historic ambiance.
As lovely as those B&Bs are, they aren't quite my style (or in my budget!) We chose to stay at Hyatt Place in Vilano Beach and were pleased with our choice. The hotel is newer and it shows, everything was pristine and the staff was incredible. It's in a great location, with plenty of little shops and restaurants, even having a Publix right across the street. The beach is just down the street and the valet will shuttle you down if you would like.
Day 1: Arrival + Downtown
Highlights Include:
Columbia Restaurant
Castillo de San Marcos National Monument
Flagler College
Lightner Museum
St. George Street
River and Fort Restaurant
Since we arrived late at night, we decided to stay overnight in Jacksonville and head out in the morning. The drive was an easy straight shot and we went directly to our first stop: a historic tram ride tour. One of the perks of the tour is you get free all day parking and they even offered pickup and drop-off anywhere downtown, which was a huge convenience.
However, I have to admit, the tour itself was a bit underwhelming. While it allowed us to get a good lay of the land, the guide didn't really speak much about the city's history and mostly kept pointing out B&Bs. It wasn’t a total loss, since they dropped us right off at the restaurant we wanted to go to for lunch!
For lunch, we went to the famous Columbia restaurant, a beautiful Spanish style restaurant that came highly recommended. We kicked things off with their hot house made bread and virgin mojitos that came with sugar cane sticks.
That little touch immediately transported me back to childhood, when my grandfather used to bring me sugar cane when he visited from South Carolina.
As for the meal, I went with the Cuban sandwich and salad combo. The salad was delicious, the sauce was tangy and light and the sandwich was good, though I could've used more mustard. It was the perfect amount for lunch.
After eating, we walked along St. George street, the main throughway, is lined with shops and restaurants, making our way to Castillo de San Marcos National Monument.
But first, we stopped for ice cream at Mayday ice cream, which was conveniently right across the street. They had so many unique flavors and let you try as many as you would like! After quite a few tastes I landed on the passion fruit golden milk, one of their limited time flavors.
Entry to the Castillo de San Marcos National Monument will run you $15 and you'll gain 7 day access to this fortress, though I can't imagine why you'd need that many days. On the lower level you can explore rooms filled with exhibits on the different artifacts and notable figures. The upper level offers impressive views of the cannons used to defend the wall and walk along the perimeter of the impressive structure.
We probably spent about an hour here taking pictures and educating ourselves before heading off to visit some of the downtown museums, starting with Flagler College. What is now a small liberal arts college was once the opulent Grand Ponce De Leon Hotel, one of the most prestigious hotels for the rich and famous, opening in 1888. It even had electricity four years before the President!
One of the most jaw-dropping features inside is the largest display of Tiffany's glass containing 79 original windows -- which now adorn the college's dining hall. Can you imagine eating next to priceless history, wow. Some notable guests include Robert Frost, Mark Twain and Babe Ruth. Unfortunately, the building was under construction during our visit so we were not able to conduct a tour, but I highly recommend it if you have the chance.
Directly across the street is the Lightner museum which used to be another lavish hotel, before being sold to Mr. Lightner to house his impressive collections. Lightner believed everyone should have a collections hobby and houses various depictions of those within.
I think he'd be very happy to know about my souvenir penny collection I've been working on since I was nine!
After soaking in all that history, we finally head to our hotel to actually check-in and rest a bit before heading off to dinner. We dined at the River & Fort Restaurant & Roof Top Lounge. You would've noticed this beauty while walking around Castillo. It's huge with three floors of dining, despite it's size, the place was absolutely packed both inside and out.
The star of my meal definitely was the chicken and dumplings. The chicken was crunchy and well seasoned and the accompanying collard greens were sweet with a nice kick. After a delightful dinner, we headed back to the hotel and that concluded our first day!
Day 2: Vilano Beach + Lighthouse
Highlights Include:
Vilano Beach
Lighthouse and Maritime Museum
St. Augustine Beach
Floridian Restaurant
Sunset River Cruise
You can't visit a beach destination without going to the beach at least once! We decided to start the day at the beach by our hotel. We took advantage of the valet service to take us down, despite it being a 5min walk, hey technically we already paid for it!
Surprisingly this beach didn't have vendors selling umbrellas or chairs. This is very common where I'm from so it came as a bit of a shock. Instead you can pay for someone to bring you some, but it's like $50 and we weren't planning on staying that long.
Once we got settled, we actually went and swam in the ocean for a bit. I have not swum in the ocean in years. It was so refreshing and the water was the perfect temperature. There was a skimboarding competition that day, so it was cool to watch that as well and added to the fun atmosphere.
After wading in the water for a bit, these nice ladies invited us to sit under their tent to escape the sun. Boy was I thankful, because I was just about to leave because my skin was burning!
Once we've had our fill of the beach we get ready to head over to the Lighthouse and Maritime Museum. This area comprises about four mini museums and you can climb the 219 steps to the top of the lighthouse for stunning views.
Next, we drove down the street to Anastasia State Park, which contains various trails and another beach. Honestly, we decided it was too hot and didn't stay long, but you can easily spend a few hours here hiking and exploring nature.
After a little downtime at the hotel, we made our way to the Floridian Restaurant back downtown. Another delicious choice with the shrimp and sausage pilau, special shout to the hot honey buttermilk biscuit.
Our evening excursion was a sunset cruise with Florida Water Tours. I love a good river cruise and this did not disappoint. Our guides were hilarious and informative. The tour was also BYOB and everyone was just having such a great time singing along to the music selections, the energy on the boat was awesome.
I didn't realize we would be looking for dolphins on this tour. We ended up seeing one completely leap out of the water! It did it twice, they were absolutely showing off. It was such a magical way to end the day.
Day 3: Old Town + Fountain of Youth
Highlights Include:
Sunday
St. Augustine History Museum
Old Jail
Oldest Store Museum
Hop on Hop Off
Ponce De Leon Fountain of Youth and Archaeological Park
Today is all about viewing the sites of the Old Town, but first breakfast. We forgoed the complimentary hotel breakfast and walked down to Sunday a brunch spot just a ten minute walk from the Old Town hop on hop off stop where we parked for free after purchasing our tickets.
Sunday has a nice mix of shaded outdoor and indoor seating, serving your classic fare in an easy breezy setting. After having a delicious eggs benedict, we walked back to Old Town to start our tours.
We started with the St. Augustine History Museum for a self-guided tour. This along with the next few spots I mention were included with the purchase of the trolley ticket. These spots are all super touristy, but I think they are still a fun time!
Right next door is the real Old Jail, now turned into a museum. Remember how the Ponce de Leon Hotel was the go to spot for the wealthy? Well Henry Flagler knew the city needed to be beautiful, so naturally even the prison needed to be aesthetically pleasing. I've never seen a pink jail with an open porch, have you?
Flagler even had the jail relocated from the center of town, as it originally sat right across the street from the hotel, where the Lightner Museum currently stands. The 40 minute guided tour takes you through the jail, it's both entertaining and informative--great for adults and kids alike.
Right across the way you can visit the Oldest Store Museum. This 20 minute guided tour shows you exactly what an old general store would look like back then and shows some of the somewhat quirky and amusing inventions.
Old Town is a truly fantastic spot for families, there are many fun things to do and see. Right next door is the Fountain of Youth, but more on that later!
Once we had our fill of Old Town, we hopped on the trolley to start the guided tour. Sure, it's super touristy, but hop on hop off rides can still be a blast. You get to hear little tidbits about the different sites, get a lay of the land, and have easy transportation for the day.
We decided to get off at the Memorial Presbyterian Church, which has a rather poignant history. Henry Flagler built it in memoriam of his daughter and grandchild who passed. He demanded that the building be completed within a year so it would be open on the anniversary of their passing. Though tragic, it left us with an architectural marvel. The church is open to visit on Friday and Sunday. If your trip coincides with those dates, it's definitely worth a visit.
We took a slight detour before hopping on for the remainder of the tour and walked over to the Hyppo Gourmet Ice Pops on St. George street. This spot caught my eye our first day and I just knew I had to go back.
I'm so glad we did, this hands down was the best popsicle I've ever had! Made with all natural flavors they have so many options sure to please any palate. I got the watermelon hibiscus, which was crazy good and refreshing. I seriously looked into franchising, I was so into this pop.
We continued with the tour, getting off at the Ponce de Leon's Fountain of Youth Archaeological Park. When you enter they hand you a map, which provides not only locations for the various activities, but gives performance show times to plan your time accordingly. At the park you can drink from the legendary Fountain of Youth and get eternal health...pretty sure it's just sulfur water, which does have health benefits!
All in all it's a really cool park with a host of activities that show what time was like back in the 1800s. The blacksmith showcase was a personal favorite.
I was also told the BBQ is pretty solid. Once complete we headed back to the hotel for dinner on the rooftop and called it a day.
Final Thoughts + Buc-ee's
There you have it, that's how I spent 3 days visiting St. Augustine. The trip provided relaxation, history and some darn good food. I usually try to balance light and heavy food, but this was a super hearty trip. At least you'll get some good steps in!
Heading back to Jacksonville we saw a sign for Buc-ee's. I've heard of this spot before with people comparing it to Wawa and boasting how much better it is. I told my mom we absolutely have to check it out. She had no clue why, but we needed to top off gas anyway.
This is not comparable to Wawa in the slightest! I love Wawa, but Buc-ee's is an experience. I was immediately shocked when we even pulled up, this place is huge. The food section is astounding watching fresh brisket be chopped up live. I was not expecting any of this.
We decided to get some sandwiches for the road. While talking to the cashier we were informed what we were seeing was nothing. On the weekends you can expect hoards of people, we're talking shoulder to shoulder and people are dropping 1k+ on merchandise. What?!? It's like freaking Disney for some people.
Now I don’t know about all that, but I will say it was a highlight of the trip. At the airport I finally dug into my brisket sandwich….I am so glad we don't have these stores in the northeast because I would be eating these bad boys on the regular.
Okay, that's enough about a gas station lol. If you liked this itinerary, make sure to subscribe to see more. If you’re planning your own St. Augustine adventure, I’ve put together a Google Maps list to make things easier. Happy travels!
