Updated: Jul 20, 2021
2 days in the oldest city in the US. Where to stay, what to eat, and what to see.
St. Augustine is America's oldest city, and a favorite weekend trip for many across the state of Florida & Georgia. From the shopping, food, ghost tours and more, there is plenty to see on your weekend here.
I recently spent my 27th Birthday Weekend here, and this is what I'd suggest for a 2 day itinerary if you want to sample a bit of everything that the city has to offer.
Staying in the historic district will put you close to all the action, but it will also cost you an arm and a leg. I'd suggest grabbing a budget option over at the beach.
Although it means that you'll have to drive into town (about a 10 minute drive), you'll also be able to get away from all the flocks of people at the end of the day and enjoy a slower start to your morning. A super nice bonus, you get to drive over the bridge and tons of sailboats every morning on your way into town.
Don't worry, there is a super convenient all day parking garage right next to all the action, so bringing the car into town isn't a problem at all.
Where we stayed
If you want luxury over budget, I'd suggest the Embassy Suites by Hilton St Augustine Beach Oceanfront Resort. Prices run around $300 - $400 per night there.
We decided to stay about 50 feet across the road from it at Regency Inn & Suites for under $100 per night after taxes and fees. For a budget hotel, it was actually pretty nice after a recent remodel, and the location was PERFECT!
A unique stay - The dream
There are plenty of unique stays in the area, and one that I've got on my list for the future is this super cute sailboat on Airbnb.
Prices vary depending on the time of year, and availability can be a bit tricky during peak season, but with St. Augustine having such a deep history with sailing, you might also be craving some time on the water.
Day 1- Saturday:
Waking up to a beach breeze on a Saturday monrning with nothing else to do for the weekend but to explore was an amazingly refreshing start to the day. There are plenty of breakfast options available on the beach, and they offer a more relaxing start to the day by the water before heading into town.
Breakfast on the beach
My recommendation: The Kookaburra Beachside
This place started getting realy busy around the time that we showed up, and we had to park along the side of the road. Be prepared for that if you don't get there early.
On that note, I'd suggest having a member of your group grab a spot outside on the patio while someone waits to order and grab the food so that you have a guranteed spot to relax in and eat breakfast.
What to eat:
For drinks we grabbed the Mocha Nut Latte with Chocolate and Coconut and a hot chocolate. Both were a delicious start to the day.
For food, I'd highly suggest any of their Australian Brekki pies! Not only are they super unique, but they're filling and cozy.
Head into town for the day
Need parking? Skip the expensive and cramped street parking and head for the parking garage across from the Fort.
Here's where we parked for $15 all day: 1 Cordova St, St. Augustine, FL 32084
Things to do:
Explore the fort
If you've only got 2 days in the city, I'd suggest walking around the outside of the monument and skipping the huge lines. There are plaques all around it as you venture around, and you'll still learn tons of history. You'll also get great pictures without being packed inside.
If you've got more time or really love history, it's definitely worth braving the lines and crowds to get inside and see what life was like for those that spent time inside the fort.
Enjoy the sailboats
All along the river, saolboats dot the water. Enjoy watching them wave in the wind as you walk down to check out the Bridge of Lions from the Ocean Dock.
Step back in time
Even if you skip the entire tour like we did, do yourself a favor and at least check out the gift shop for the Pirate Museum. Along with tons of pirate themed items, you'll also come across real coins that were salvaged from a shipwreck and are now available for purchase.
Shop in the Colonial Quarter
This one can easily take up a good portion of your day. Meander along St. George Street to check out all the shops, step back in time at the Pirate Museum, and grab a bite at any of the restaurants along the way.
You'll find tons of charming old buildings, unique gifts, and nautical home decor
Book a ghost tour
We booked the Ghosts & Gravestones trolley tour and had a really great time. Not only is it something to do to see the town at night while you get off of your feet, it's also a great way to learn about some of the history of the place while you're there.
I personally don't believe in hauntings, but I always love hearing about the local history. I will say though, I've never had any problems with my camera until that tour.
While we were parked outside of the Old Jail, my camera started flashing red and acting crazy. None of the buttons were working. It started working normally as we drove away. When we came back around and landed in the same spot, it did the exact same thing again.
Take a look at the pictures that came out of it malfunctioning:
After a busy day in the Historic Disctrict, we chose to have a more relaxing day this time. We decided to skip breakfast before checkout and head straight for an early lunch.
My recommendation: Harry's Seafood Bar & Grille
Our hotel had a coupon book upon check-in and it had a 20% off the entire bill for Harry's. This was a great way to get some top quality food with a discount!
In terms of parking, I'd suggest the same parking garage as last time to avoid the hassle and time sink that comes from searching for street parking in that area.
According to our ghost tour from the night before, the upstairs restroom is haunted by the little girl that used to live in the house before it was turned into a restaurant 👻
What to eat:
I'm honestly not a huge fan of fish, but I decided that this was probably a place that wouldn't let me down. I went with the Andouille Crusted Grouper and WOW was it fanstatic!!! A side of rice & beans and I was in heaven.
For dessert, we followed it up with the oreo biegnets and the banana's foster. I can't imagine anyone in the group being let down by those biegnets to be honest. Definitely a crowd pleaser!
Things to do:
Pop over to Cordova Street
Check out some absolutely beautiful architecture that you won't find anywhere else in Florida, and maybe the U.S. in general. From Flager College to the Casa Monica Resort & Spa, you won't be let down by the eye candy this part of the city has to offer.
Need to pick up a gift for someone else (or yourself) before heading out of town? This area has artisan soaps, name brand bags, and top brands for you to peruse.
Visit the St. Augustine Yacht Club
As you head out of town, stop by to check out this secluded little spot where families are learning to sail and you can get a beautiful view of the lighthouse. It's a great relaxing way to end your trip.
We loved our St. Augustine weekend, and hope that you do too. Check back in for more travel itineraries to come!
Thanks for reading!