St Augustine Weekend Guide

At the beginning of June I took the perfect early summer trip down to St Augustine Florida with my mom for a little girls weekend of R&R (aka lots of good food & beach time). Now that I’m a bit further out of school and have more vacation days it’s been so fun getting to take more short trips with family and friends! Before this trip, I truly knew nothing about Florida (except for Disney World) and it’s gorgeous beaches, so I was excited to finally see why so many people love it!

Why go to St Augustine?

Honestly, I could list DOZENS of reasons to head to St Augustine. It’s rare that I find beach towns I really love and would go back to, but St Augustine hit everything I was looking for.

First off, if you’re going to Florida you want great beaches and there are amazing ones around St Augustine! As a northener (lol) I was so happy with how warm the water was in early June!

What would really bring me back to St Augustine though was the quaint historic downtown. Fun fact, St Augustine is the oldest city in the US, and it shows when you walk around. There are gorgeous old buildings every direction you look that I couldn’t get enough of. I honestly could have spent week just exploring and photographing the area! My biggest pet peeve with beach towns is when everything is way over touristy and tacky, so one of the reasons we loved St Augustine was the perfect mix of your classic beach town and a historic destination.

Getting To & Around St Augustine

St Augustine is on the northern Atlantic coast of Florida! To get there you’ll want to fly into Jacksonville and then drive about an hour south! Since I was traveling with my mom we rented a car, which I would highly recommend. If you’re staying by the beach you’ll want to easily be able to get to town and vice versa. However, if you can’t rent a car (like me for another year), you could definitely use Uber to get back and forth!

*We didn’t have much issue with parking in Old St Augustine during they day, just driving around a bit to find parking lots with empty spots, but I definitely recommend having a driver who is confident driving through crowded areas and small streets!

Where to Eat & Drink

Since I only had 3 days in St Augustine I by no means got the full food tour of the city, but that’s one of the main reasons I want to go back! From the research I did ahead of time there were so many delicious looking spots I’d be sure to go to! A few spots I wanted to go that we didn’t get to include the Ice Plant Bar for cocktails, Harry’s Seafood for New Orleans style food, and Catch 27 for the great outdoor seating!

Cap’s on the Water

I have to start by saying this was one of the BEST restaurant experiences I’ve had in my life. Cap’s on the Water is a bit of a drive out of town, but worth it a million times over. Set right on the water with a huge deck and pier it’s the absolute perfect place to spend sunset. I wish my pictures even did it a bit of justice, but you really have to be there to understand just how magical the location is.

Since we went to celebrate a belated Mother’s Daym my mom and I went all out food wise. We ordered the Fried Green Tomato Caprese to start and I think I was literally drooling while eating it. Then I had one of the fish specials of the night which somehow beat the Caprese (which I didn’t think was possible).

One callout, Cap’s doesn’t take reservations so I recommend showing up early to put your name in and grabbing a drink at the bar. I had the spicy margarita and as you’d probably guess it was great!

The Kookabarra

Living in NYC I love a good Aussie Coffee Shop, so The Kookaburra was on my must stop by list. There’s actually a few locations around St Augustine and it’s the perfect quick breakfast spot to have a GREAT coffee (something that can be so hard to find outside cities) and one of their Aussie Pies (almost like a quiche with a little more breading.

What To Do in St Augustine

My number one reccomendation if you’re headed to St Augustine is to spend at least half of each day on the beach becuase it honestly just can’t be beat. However, if you’re like me and need activities to fill the rest of your time (I don’t do well with ‘chill’ time) there is plenty to do!

St Augustine Lighthouse

Seeing the local lighthouse is a requirement for basically every trip I take, so I convinced my mom to walk up all 219 steps of the St Augustine Lighthouse on our last morning. The view from the top is absolutely gorgeous and I definitely recommend going in the morning because the sun is in the perfect direction lighting up all of Old St Augustine.

Old St Augustine

This may seem obvious, but wandering around Old St Augustine is a must do during your visit! I could not get enough of the gorgeous architecture and specifically recommend stopping by the City Hall for the beautiful garden in it’s courtyard as well as the Flagler College campus because those buildings were some of my favorite!

Castillo De San Marcos

Castillo de San Marcos is a fort located on the edge of Old St Augustine looking out over the water. It’s actually the oldest standing masonry fort in the United States having been completed in 1695. While we didn’t do a full tour of the fort (tickets were a bit $$$) we did walk around it’s perimeter which gives you great views of the fort itself and the surrounding bay. If you’re traveling with kids or have more time in St Augustine I’d recommend taking the full tour since looking back I’m a bit bummed that we didn’t!

What to Pack & My Outfits

Keep things light and airy when you head to St Augustine! It was seriously humid in early June and even in the evenings I didn’t really need the lone denim jacket I had brought along. With St Augustine being such a picturesque destination I wanted to pack a few cute outfits to go further than my usual jean shorts + t-shirt beach attire, so I’ve linked to my outfits below!

Outfit 1: DL1961 White Dress, Soludos Wedge Espadrilles, Vintage Scarf, Bamboo Bag

Outfit 2: PacSun tie top, American Eagle Red Skirt (similar), Soludos Espadrilles, Bamboo Bag

Outfit 3: Cuyana Hat, American Eagle t-shirt, TJ Maxx Shorts (similar), Soludos Sandals

Outfit 4: Cuyana Hat, American Eagle Dress, Bamboo Bag, Soludos Sandals

Looking at this now I”m laughing because American Eagle was clearly the MVP of this trip! If you’re looking for cute vacation pieces at a reasonable price I definitely recommend perusing the site!

PS Don’t miss my other travel guides for Curacao and London!

Shop My Outfits

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