St. Augustine is the oldest continuously inhabited city in the continental US. The city was settled by Spanish colonizers in 1565!
In 24 hours, Kim and I had a whirlwind, self-guided tour of the main walking part of the city called “Old Town.” We ate delicious food, explored shopping, observed various opportunities for museum visits and tours, and so much more!
In this post, I give twelve recommendations for various experiences you can have. Each suggestion is accessible along the main tourist street or just beyond it.
1. Walk St. George Street
St. George Street is the main, commercial walking street of Old Town in St. Augustine. Stretching from Cathedral Pl. to Orange St., St. George is a less than half mile walk of historic sites, shopping, bars, restaurants, live music, museums, and more.
The architecture and older, renovated buildings alone had me gazing up and all around.
There is lots of observe and do up and down this short strip and much of what I share below can be found right on St. George or within a short walking distance from it.
Don’t forget (like I did!) to check out the Old City Gate right at the end of St. George on Orange St.
2. Go Shopping
All along St. George street there are many different shops including your typical souvenir touristic shops.
I enjoyed finding and exploring some of the specialty stores. One of these, off St. George on Cuna Street, is the Golden Gypsy which has some hippie-style art and hand-made accessories. I loved this shop and bought a piece of art for a friend. I really appreciated their LGBTQ-friendly vibe, too!
There’s also more on-theme specialty stores like St. Augustine Textiles. You can easily miss this shop as it accessible off St. George but slightly tucked away off the beaten path.
St. Augustine Textiles has handmade, authentic colonial clothing and accessories from the 1500s to 1700s. The items here are amazing and are typically made for historic re-enactments, theater, school plays, and costume events.
Appropriately right outside St. Augustine Textiles is a medieval pillory to take photos!
3. Eat At Columbia Spanish Restaurant
There are many great restaurant options in St. Augustine. But Kim swore that Columbia was the best. So we made a reservation and it did not disappoint!
Columbia has a rich history through the prohibition era, welcoming home troops from multiple wars, and making it to its 75th and 100th anniversary celebrations. Multiple generations over this restaurant has stayed in the family, and so has its recipes!
One of the most famous recipes is one of its most basic courses: The “1905” Salad. I was skeptical when Kim told me I had to taste it. “Iceberg lettuce?” I thought, “Meh.”
They make a big deal out of it, though—putting all the ingredients together right in front of you!
They aren’t so secret about what goes into it. The wall of the restaurant includes the recipe right on it!
Finally tasting it, I understood why people love this salad. The not-so-secret to this salad is in the dressing! And it’s soooo tasty!
Apparently, don’t judge a salad by its look! This salad placed Columbia Restaurant on USA Today’s list of “10 Great Places to Make a Meal Out of a Salad.”
Our server recommended I try the Salmon St. Yago, which is a Fresh Verlasso Patagonian salmon fillet baked in parchment paper with shrimp, crabmeat and artichoke heart stuffing with fresh tomatoes and asparagus and served with yellow rice. She promised it would not disappoint and it did not. This was possibly the best salmon I’ve ever eaten at a restaurant!
With Queso Fundido (cripsy Cuban bread dipped in melted cheese) and a flan dessert to top it off—I was in Spanish food heaven. And that’s saying something coming from Miami which is Spanish food central!
This was next level, for sure. I would definitely be a repeat customer if I lived closer!
4. Visit Castillo De San Marcos
You definitely don’t want to miss visiting Castillo de San Marcos while in St. Augustine. Just steps from St. George street, this Fort was built between 1672 and 1695 to defend against France and Great Britain invasion. There’s so much to explore here, so much history, and it even feels little like being in an Assassin’s Creed game!
In a previous post, I wrote extensively about my visit to Castillo De San Marcos if you’re looking for an extended overview.
5. Get Hyppo Gourmet Popsicles
Popular popsicles? That’s right, St. Augustine randomly has a popsicle shop that has quickly become a favorite attraction. They make gourmet, healthy popsicles made from crushed fruits and spices in some consistent favorites and rotating newbies.
At the corner of Charlotte and Hypolita, find a flavor that fits your fancy. There’s every kind for every type of “tooth” from sweet to spicy and everything in between.
I got blueberry cinnamon and it tasted like blueberry French toast at Sunday brunch.
6. See The Torture Museum
This is the first museum I spotted off St. George Street. This is a museum dedicated to this barbaric form of punishment and all of the paraphernalia that came with it. You don’t even have to enter the museum to begin gawking at the examples hanging on the walls leading inside.
We didn’t go in but tickets range from $20-$30. For those with an interest, I bet it’s a really interesting and educational experience!
7. Try Wild Popcorn Flavors
Okay. This may have been my favorite surprise during my visit to St. Augustine. Kernal Poppers is a gourmet popcorn shop featuring rows and rows of different flavored popcorn. They have almost any combination you can imagine from “Loaded Baked Potato” to “Twix” candy bar.
Just look closely at some of the labels in the above photo or this one below!
The best part is how incredibly generous they are with allowing different samples. They literally didn’t stop sharing. You would ask for 2 kinds to try and then the people next to you might ask for 2 different kinds and so they share those with you, too. Next thing you know, you’re trying 4 kinds and you still have 2 more you want to try. If you keep asking, they keep sprinkling more onto napkins in front of you.
I think I tried about 15 different kinds by the time we left there. At almost $15 for a large bag, we easily bought over $45 of popcorn each—that is how they get you! But these bags lasted me a while and they were so good.
Below you can see the man who makes them behind the scenes. He happily posed for a photo. Hats off to you, sir!
I believe the flavors I settled on were: Bacon Cheddar, Lemon Shortbread, and Caramel Sea Salt.
The Zebra, Truffle Oil, Blueberry Cheesecake, Peanut Butter Chocolate, and Everything flavors were the runners up for me!
This popcorn was well worth the price tag. I am even considering buying some to be delivered because it was that special and delicious!
8. Tour the Oldest Wooden School House
Who knew someone was even keeping track of the ages of all the wooden school houses in the USA? Apparently that’s happening because St. Augustine claims to have the oldest!
It’s not as old as the city, though, because wooden structures in St. Augustine were burned down in 1702. Go read my post about Castillo De San Marco to learn that back story. But records show this wooden school house was standing since 1716.
You can take a tour of this schoolhouse to see and learn about it from the inside. But I could admire it just from the outside! How cool is that? And what is with the chain?
9. Check Out The Pirate Museum
Here’s another museum tour that I did not bother to get tickets for. We just didn’t have enough time after we spent most of our time at the Castillo. But I know that pirates are a huge attraction. I love anything to do with pirates! So I’d love to check out a pirate museum one day whether it’s this one in St. Augustine or the one in Provincetown, MA.
10. View the Flagler College Architecture
I had no idea there was a college this beautiful in St. Augustine. Flagler College (which I honestly never heard of before my visit) is now in the building of the former Ponce de Leon Hotel.
We visited during a downpour of rain. But if you go strategically between 10:00am and 2:00pm on any day, Flagler College offers tours of the public spaces of its buildings.
Henry M. Flagler, builder of the Florida East Coast Railway, built the Ponce in St. Augustine in 1887. The landscape and the architecture and the details both inside and out are just amazing! I couldn’t believe that students take classes there, eat in a dining hall, and sleep overnight in the residence halls inside this building. I hope they don’t take for granted how beautiful their campus is!
11. Take A Trolley Tour
For those who maybe can’t walk by foot or who prefer to cover more ground in a shorter timeframe, a trolley tour is a great option!
It’s about $32 for 1 full day of unlimited reboarding. So you can hop on and off at all the places you want to see! The guides will give you a ton of interesting history that I’m sure you wouldn’t get otherwise.
12. Create A Vintage Photo
I actually can’t believe I’ve never done one of these before. Kim and I happened upon one of these shops during our walking tour of St. George Street. Victoria’s Vintage Photo is on a little side street next to the Oldest Wooden Schoolhouse. It was closed the day we found it but the photos on the door looked amazing.
Being in the oldest city in the USA is a great time to get one of these photos if you’re into that sort of thing!
13. Stop By The Governor’s House
A final historic site you can check out is the Governor’s House which has stood there since 1598!
Previously the administrative headquarters and residences for colonial governors of Spain and Britain, the location is now a part of the University of Florida and remains a cultural center and museum.
It often holds weddings of up to 120 people.
In Conclusion
My short stay in St. Augustine afforded me the opportunity see, eat, and do much! This list will help you get started if you are planning a visit. If you can, try to spend at least 2 days here so you can choose a museum or two to check out and still get a chance to hit the other things on the list. Oh, and don’t forget to check out the local lighthouse, too!
In the coming weeks, I’ll be revealing some exciting travel plans I have coming up. Stay tuned for the scoop!
