Earlier this month, my boyfriend, Matt, and I decided to go to the Florida x Georgia game in Jacksonville — go Gators! St. Augustine has long been on my bucket list, so when we realized it was the perfect spot to spend a few days in before the game given its proximity to Jacksonville, I was very excited. ‘America’s Oldest City’ did not disappoint — I loved the architecture, the history, the food, all of it!

We flew from DCA to JAX on a Thursday afternoon, rented a car, and made the short drive to St. Augustine. Once we were in the historic district, we were able to walk and Uber everywhere, which was so nice! We stayed in town through Saturday morning, when we hit up Publix for tailgate accruements and headed to EverBank Stadium for the game. While I definitely want to make a return trip to St. Augustine someday, we agreed two days was the perfect amount of time to explore — the historic downtown is on the smaller side, so we were able to do everything we wanted to do without feeling rushed. If we had stayed another day, I would have wanted to check out one of the local beaches or gone out on a boat.

Below, I am sharing a complete recap of where we stayed, where we ate + drank, and what we did. Though we just missed it, St. Augustine’s ‘Night of Lights‘ that runs from late November to late January annually looks incredible — decorations were going up while we were in town!

St. Augustine Weekend Travel Guide

Where to Stay in St. Augustine —

I had enough Marriott points to book our two-night stay in St. Augustine, and was between booking the Renaissance St. Augustine Downtown or the Casa Monica Resort & Spa, Autograph Collection. As they were both centrally located in the historic district, either would have been a great option, but I ended up going with the Renaissance as it was 20K points cheaper.

We really enjoyed our stay! The hotel itself is architecturally stunning, with buildings that were Victorian in style and thus very reminiscent of the Gilded Age. Completed just a few years ago, it was designed to pay homage to the iconic Hotel San Marco — a major competitor of Henry Flagler’s hotels in St. Augustine — that burned down in 1897. Our room was spacious, clean, and well-appointed. But the biggest perk of all was the location — other than taking an Uber to dinner one night, we were able to walk everywhere, which is something I love to do when traveling as you really get a sense of a place when you can enjoy it on foot.

Where to Eat & Drink in St. Augustine —

St. Augustine has a really fun dining scene — we didn’t have a bad meal while we’re in town! Here’s where we ate and drank:

St. Augustine Fish Camp

his was a casual, coastal restaurant located right on the water and if you’re in the mood for seafood, this is a great option! We started with a special of the day, which were these amazing scallops on the half shell served with a cream sauce that had bacon and sun-dried tomatoes. Those might have been the best scallops I’ve ever had! For my main, I did a broiled seafood platter that had a white fish, scallops, and shrimps served alongside veggies and potatoes.

Ice Plant Bar

After Fish Camp, we made the short walk over to the Ice Plant for a night cap. This was my favorite place we went the whole trip! The bar is located in the old industrial building where they used to make and cut ice, and they still have the original crane bridge rails on the walls above the bar. It had a moody, dark, upscale vibe and the cocktails were excellent. They also have specials everyday, so we were able to score amazing daiquiris — not the beach-y, frozen kind, but the kind served in a champagne couple — for just $6!

Maple Street Biscuit Company

We started our long day of exploring here on Friday, and I loved it from the moment we walked in. Instead of calling out your name when your order is ready, there is a question of the day and they call out your answer. When we were in, the question was, “what is your favorite holiday food or drink?” (I said beef tenderloin and I stand by it!) I did a hash bowl with potatoes, spinach, bacon, mushrooms, peppers, onions, and two eggs over easy topped with everything bagel seasoning. But I also couldn’t go to a biscuit place without ordering one — so I got one on the side with their amazing raspberry strawberry jam.

Pizza Time

Matt is a pizza connoisseur, and he stopped into this place for an afternoon slice. While I held out for empanadas — more on that below — this place was legit and smelled amazing! If you’re looking for a casual meal after a long day of exploring, an afternoon snack in the AC, or pie to take back to your hotel room, this is the place.

The Cuban Cafe & Bakery

I love empanadas and opted to stop into The Cuban Cafe for my afternoon snack. I tried both the chicken and the beef. And we sat outside on their lovely courtyard patio to do some people watching while I enjoyed. I don’t like coffee, but this place apparently has great Cuban coffee if you’re in the market!

Prohibition Kitchen

We went to Prohibition for a happy hour drink and it was so much fun! While we were in on a Friday night, they had a live jazz band, which really set the vibe. Their windows are covered by dark curtains, which really give it that speakeasy vibe — and I loved that they had copies of the newspaper announcing that Roosevelt ended Prohibition at the host stand. They have a huge bar that we posted up at and enjoyed another daiquiri — when in Rome!

Columbia Restaurant

We ate dinner here on Friday night, and if you’re in St. Augustine, you have to get a reservation here! We loved it — and you can tell they do good business because this place was bustling. From the moment we stepped in the door, it was a great experience — there are gorgeous Spanish tiles everywhere and the meal here was an experience. They brought us each out a loaf of warm Cuban bread, served alongside whipped butter. We started with the 1905 salad, which was made table side. Matt did the paella, which looked amazing, and I did the ropa vieja, which was perfectly tender and flavorful.

Casa de Vino 57

After dinner, we went on a walk since we were so full, and heard live music, so we went to check it out. That’s how we stumbled into Casa de Vino 57, which was such a fun place for a nightcap! It’s a wine bar in a beautiful courtyard that has huge trees draped in Spanish moss. The band they had was really fun, and it was the perfect way to cap off a great evening.

Juniper Market

Located just a few blocks from our hotel, this was a super cute coffee shop with a made-to-order menu of breakfast sandwiches, burritos, and the like. I did an incredible pita with scrambled eggs, bacon, avocado, and sriracha mayo. Simple, but so tasty!

What to Do in St. Augustine —

One thing I especially love about St. Augustine is how walkable the historic old city is — it makes it easy to explore on foot while enjoying the cobblestone streets, the water views, and all the palm trees and Spanish moss. Here’s what we did that I would recommend adding to your itinerary:

Visit The Lightner Museum

Set in the former Alcazar Hotel, which was built by Henry Flagler, The Lightner Museum houses an eclectic collection of art, antiques, and curiosities — from Tiffany glass to vintage instruments. Don’t miss the central courtyard, which houses a beautiful fountain, or the former indoor pool, which now is a charming café. The architecture alone is worth a visit and the exhibits provide a fascinating glimpse into 19th-century opulence alongside some of the history of St. Augustine as a resort town.

Stroll Across the Bridge of Lions

Connecting downtown St. Augustine to Anastasia Island, the Bridge of Lions is more than just a roadway — it’s a piece of history. Completed in 1927, this elegant drawbridge was built during a period of rapid development, originally designed to facilitate growth on Anastasia Island. Though the boom didn’t last, the bridge remains an enduring icon of the city, recognized for its striking architecture and historic significance — it’s even listed on the National Register of Historic Places. Renovated in 2010, the bridge continues to offer scenic views over Matanzas Bay and stands as a beautiful reminder of St. Augustine’s storied past. Stop by at sunset for a truly magical moment!

Visit the Castillo de San Marcos

No visit to St. Augustine is complete without stepping into history at the Castillo de San Marcos. This 17th-century Spanish fortress, the oldest masonry fort in the continental U.S., stands as a testament to centuries of conflict and culture. Walk the ramparts, peer through the ancient cannons, and imagine life here in the 1600s. The panoramic views of the bay from the top are worth every step!

Shop on St. George Street

This pedestrian-only street in the heart of the historic district is lined with boutiques, galleries, and cafes. Whether you’re looking for the perfect souvenir, place to grab an empanada, or just want to enjoy the Spanish architecture, you definitely have to take a stroll down St. George Street during your trip to St. Augustine.

After our time exploring St. Augustine, we packed up our rental car, hit up Publix for some pub subs (if you know, you know!) and cookies (they have the BEST cookies!), and made our way to Jacksonville for the Florida x Georgia game. It was my first SEC game and was so much fun! The people watching alone was incredible — there were tailgates everywhere! We stayed in Jacksonville the night following the game and flew home the next morning.

I would go back to St. Augustine in a heartbeat — if you have any questions about our trip, feel free to drop me a comment below.

Below are more of my favorite pictures from our trip — until next time, St. Augustine!