The Best (and Tastiest) Things to do in St. Augustine On A Mother Daughter Trip

Did you know St. Augustine is the oldest city in the USA? It is! You can step back in time to actual forts used hundreds of years ago, wander the old fashioned alleys of St. George Street eating fudge and caramel apples, and visit the beach as well. There are so many things to do in St. Augustine and in three days I’m sure we barely scraped the surface – but not for lack of trying!

I planned out so many fun unique things to do ahead of time and we used a local map to make sure we hit the tourist spots too, making sure there was a nice mix.

The main area of St. Augustine is St. George Street which is really like going back in time. It’s so pretty and has cool restaurants (all playing live music at night), old-fashioned candy shops and yummy chocolate like Whetstones, cool craft shops, and even a tourist attraction with the oldest school in the USA!

You can take a trolley around town with a couple of different companies, like Red Train Tours, so that you can get a feel for where everything is and then go back at your own speed, or you can actually get on and off the trolley throughout the afternoon and hit up all the places that you’re keen to visit. There are upward of 20 tourist attractions in St. Augustine and not all will be up your alley, so take a look ahead of time and see which ones are important to you.

We stayed right on St. George Street which is what I recommend. I love being right in the middle of it – it’s a family place, not a party place so you don’t need to worry about noise at night. It’s so nice to wake up, be right near the fort, and even go out there for sunrise (yes, I actually did this!).

There are so many inns to choose from, but I knew that I had to stay at the St. George Inn which was mentioned in every travel magazine as the “it” place to stay. I loved it! The rooms were huge (we actually had two rooms), a big clean bathroom, perfect location, friendly staff, and a really nice breakfast spread! You also get free parking at the parking garage which is just a 2-minute walk from the hotel.

Note that St. Augustine town where St. George Street is, isn’t where you can go swimming – you will drive to St. Augustine Beach for that. Some people prefer to stay on the beach so you can look into hotels across the bridge (it’s just 10 minutes) or even camping at the State Park.

Just outside of the hotel, across the street is the most famous attraction in town, Castillo de San Marcos. We took our coffee out there for sunrise but also visited it during the daytime to do a proper tour. You can buy tickets at the entrance to go inside, but you can walk around outside of it for free.

You could do this at the beginning of the trip so you can get a quick lesson in the history of St. Augustine and what makes it the oldest city in the USA. Ponce de Leon found St. Augustine (and all of Florida) while looking for the Fountain of Youth. This area was home to Native Americans, French, English, Spanish, and more and battles ensued. I won’t share the history because let’s be honest, I’d probably mess it up – but also because it’s part of the reason to come here. Learning about the history of the USA is cool and there are so many places to do that here.

We were lucky to visit during restaurant week so got to try some mixed menus from a couple of famous places at much lower prices. The first place we went for dinner was Michael’s Tasting Room. This is the most famous restaurant in town from what I gather and it was SO delicious. I had the short ribs (cooked all day long with a coffee flavor) and a chocolate dessert, but what stood out most was the salad. I have never said that before in my life! I loved it so much – fruit, nuts, and a great dressing. I really should try to make one myself one day, lol.

My mom’s a teacher’s aid and has worked in a school since I can remember, even as a volunteer when I was really little at my elementary school. It was fun to go check out the “oldest wooden school in America” with her. They had a sign in there that the “dunce hat” was put on the kids that were slow learners, not the trouble-makers. How mean is that!? They also had a little box cubby area where the bad kids had to go sit.

Our hotel has a wine bar called Bin 39 and you can get wine flutes for $10 here, it’s crazy. I mean, after traveling I thought Ohio was really affordable, but Florida is right there with us. You can definitely visit here on a budget… and still get drunk ;)

A trip to St. Augustine isn’t complete without a visit to the St. Augustine Lighthouse. I recently read the book Light Between Oceans and was pretty interested in the lighthouse life of the old days. The walk to the top is hundreds of steep steps but it’s really not that bad and people of all ages were doing it. The view is incredible!

For people who say America just doesn’t have the “history” that Europe has, I feel ya on the fact Europe is REALLY old, but I had no idea just how cool St. Augustine would be and how much I would learn. This is the nation’s oldest port!

If you want to do something really off-beat, then go for a salt spa! The Salt Spa at St. Augustine was brought to life by a Polish woman who grew up going to the salt spas that are so famous in Poland. In Europe, the idea of having a spa day that is all about health and relaxation is normal, while in the USA it’s more about hair and nails. Salt has so many proven benefits for your respiratory health and so many other areas of your health.

To go into the salt cave is around $30 but really quite affordable for anyone. My mom fell asleep pretty much right away – it was so relaxing. After, we went into the “pods”. What a crazy experience! You go inside these pods (below) and float in the salt water – a similar feeling to the dead sea. The salt makes you float. You stay there for a whole hour with the lid closed. Tom Brady does this before and after every game. Not only great for your body but also your mind.

St. Augustine is probably the most famous for being where the Fountain of Youth is located. Ponce de Leon thought he found it in 1513 and you can come drink from the very same spring of water. You won’t only learn about Ponde de Leon’s journey but you’ll also learn about the Timucua Indians, who were the largest indigenous group in this region.

Do mom and I look younger yet?

Before you leave, grab a bite from the BBQ place there called Smoked Southern BBQ. I know what you’re thinking – it’s got to be a tourist trip. But you’d be wrong! This is a sister restaurant to Preserved, one of the best restaurants in town, and is seriously AMAZING. I had a little bit of everything as you can see. It was really affordable as well, which is rare at a tourist site.

There is some pretty good shopping on St. George Street but actually the places we loved shopping the most was Uptown on San Marco Avenue. We saw these boutiques on the way to the Fountain of Youth and stopped after. I hadn’t read about them online before! There is a mix of homewares, antiques, and cute cafes so I think coming here early for breakfast, coffee, and shopping before you go to the Fountain of Youth would be perfect.

We also went out to the St. Augustine Outlets while it was raining one afternoon and got some steals at the Loft! I feel like you can’t go on vacation in Florida and not go to the outlet malls.

Are you already wondering how we fit this all into three days? I’m not done yet! Across the bridge from town is Anastasia Island and Anastasia State Park. We went out here with Anastasia Watersports to do some SUP with a dolphin expert from Marineland. You can see turtles and more while you’re out there and it’s just a really beautiful park to drive through as well and check out the viewpoints. It’s just $35 for two hours or you can go for an hour for just $20. I told you it was an affordable trip. My mom and I couldn’t believe that was the price. In Ohio, at Lake Erie, it’s $100/hour to rent a SUP.

You’re going to work up and appetite and you cannot leave St. Augustine without chowing down at St. Augustine Seafood Company. I think I actually devoured my fish sandwich is under 3 minutes. The cole slaw, potato salad, fries, lemonade, and the St. Augustine style Minorcan clam chowder were all so, so good. You’ve got to try the Minorcan style clam chowder, which you’ll only get in this region.

The last thing we did in St. Augustine was a food tour with Roadster Tours. We did the “wine and dine” tour and really enjoyed it. Not only was the food great, but it was so cool to just mingle with some fresh faces and get to know them. We loved our group and had so much fun – I think everyone was pretty boozed up by the end of the night since we started with a wine tasting and had a drink or two at every stop. They take you to really popular places (like dessert at the Floridian which was so freaking good and such a cool restaurant – don’t miss it) and it changes each time so you could even do this tour more than once. They have 40 places they alternate between.

You do the tour by “Roadster” which is a big four-wheeler, kind of? But it’s fun to ride around in from place to place. We actually got to see a lot of St. Augustine this way which we wouldn’t have normally seen, like fancy neighborhoods, epic mansions, and this view!

The wine tasting we started at with the beautiful fairy lights was Carrera Wine Cellar and it was amazing – such a cool place with a porch inside! The tour covers a lot of ground and I highly recommend it.

St. Augustine was SUCH a cool city and my mom is already planning to go back with my dad – and I’m trying to figure out when I can make another trip!