Two Days In Historic St. Augustine, FL.

The last time I was in historic St. Augustine, FL, I was on my fourth grade field trip buying rinky dinky souvenirs and singing singalongs on a school bus. Now, its 13 years later and my awesome girlfriends Mandy and Steph and I are headed up for a girls trip to do as much as we could, for as little money as we could, in a very little amount of time.

I had just graduated and Mandy and Steph were home on Christmas break and we felt like we all just really needed to girl it up, but on a college student budget (as per usual). 

The plan was to drive up early Tuesday morning, spend the night and come back Wednesday evening. The drive is about 3 1/2 hours from where we are in Jupiter, FL, but it's an easy drive to make, straight shot up the east coast of Florida. 

So, how do you do everything you can in the cute little waterfront town of St. Augustine in a day and a half for not a lot of money? Lets do it.

First things first, we went in December so we had chilly, foggy, windy weather. Although I don't like the cold, I really enjoyed going during this time because the Flagler College kids have gone home for break, allowing the whole city to kind of chill out and feel less congested. Also, the whole town gets strung up with lights for the winter season and they call it "Nights of Lights." The whole town just feels sweet and festive and it makes it super enjoyable just to walk around in the evening and explore a little.

We arrived and parked at Castillo De San Marcos. Its a historic fort right on the water thats walking distance to everything in St. Augustine. It does cost a few bucks to park, but with the little historic roads and the ability to walk everywhere from there, its a win/win. 

(The fort itself is a national monument in Florida, and you can learn all about it at )

Across the street from the fort is a coffee and ice cream shop, so we fueled up there with adorable lattes fit for a girls trip, and headed back over to the monument. Its a $10 entrance fee, and the fort itself is definitely cheesed up for tourists, but its a really cool piece of history and great way to see the city from the roof of the stone building. Meanwhile, we felt like kids again running through the fort and playing with replica cannons. 

Views from the Castillo De San Marcos National Monument

Castillo De San Marcos 

We then walked through Cordova and St. George streets, which are lined with the cutest little shops and restaurants and cafes you've ever seen. We shopped, ate lunch, and found ourselves walking through the beautiful Santa Monica Hotel, the even more gorgeous Lightner Museum and Garden, and the Flagler College campus (which used to be a Flagler Hotel). All three of these are in one main square and pretty much make up a triangle. You can definitely walk through all of them within an hour. 

Mandy and Stephanie in The Lightner Museum Garden

We had our heart set on a ghost tour, but the prices were just more than we wanted to spend for something that touristy. You can definitely find a great one for $20-$30 depending on whether it is a walking tour or trolley tour, but it just wasn't worth it to us right then and there. During the winter season they also have their famous trolley rides converted to accommodate Christmas light viewings, carol singing, and hot cocoa drinking, totally a must for families!

The one thing we splurged on for this trip was our bed and breakfast. We decided that if we were going to be in this cute little town for one night, we might as well do it right and not stay somewhere generic. This turned into quite the debacle which is why the bed and breakfast we stayed at will remain unnamed...more on that later. So we checked in, changed into warmer clothes, and decided to wander on over to the San Sebastian Winery for a FREE... yes, thats right... FREE winery tour and tasting. Needless to say, we were stoked. 

The winery is so great, and the run tours all day pretty much every day. And the best part about the tour? The tastings. They told us we would be tasting less than ten wines, but our guide was so fun, we ended up tasting 18... And their wines are some of the best I've ever had, and for an awesome price. We all ended up purchasing a bottle after (they were such great prices), even though they never made us feel pressured to. 

After the winery, we went out to the grand opening of a restaurant called Prohibition Kitchen (AMAZING food btw) and hung out, listened to the band, and ate giant pretzels until a little later at night before heading back to the infamous bed and breakfast.

The aftermath in the tasting room of the San Sebastian Winery

Now we address the awkwardness that was our B&B. I won't be including the name for a few reasons. One being we were pretty embarrassed. So, long story short we tried to split one room at this bed and breakfast. We are all pretty used to snuggling anyways, and the room had a king bed which was more than enough for us. The room did not allow three people but we didn't think it'd be big deal... We were wrong.

First of all, we had no idea that the owners of these B&B's hovered so much. I felt like they were constantly over my shoulder if we weren't in our room. The room that we could afford only allowed two, so we decided to reserve the room for two and just bring Mandy in with us and not say anything, since we doubted that they would even notice. The owner said something right away... "Theres three of you? Did I read the reservation wrong?" We just said no and that we were visiting Mandy. We changed and headed to the winery and dinner until later at night. When we came back we all went up to the room and fell asleep, glad the owner wasn't there when we came in. The next morning we woke up for a homemade breakfast downstairs for TWO. Mandy had wanted to head somewhere else for breakfast anyways so she walked down the back entrance of the building, went and got her food, then met us in the lobby of the B&B, conveniently making it look like she had just shown up. The breakfast was extremely structured, and slightly uncomfortable. We had gone outside to sit on the porch and the owner actually came and got us... When asked what we were doing, we simply stated we thought we'd sit outside. He then replied with, "Well we didn't set up any places outside because its too cold." Needless to say we gave up, came inside, got served our breakfast, and Mandy showed up. The owner immediately asks "So, did you end up spending the night?" Mandy just said no she hadn't and kept eating her to-go breakfast. The owner then very aggressively replies "Oh really?? Because I could've sworn I saw someone suspicious that looks just like you walking down our back steps this morning." and proceeds to walk away. Needless to say we all felt so uncomfortable over something that should not have been a big deal, and we felt a little weird that this man had been kind of hovering over us every time we came in or out, and now this. Also, our plumbing did not work... At all. So Mandy and Steph dipped to the car and let me awkwardly check out and run out the door. 

Basically, we should've just stayed in a hotel as to not have our every move monitored and our schedule set for us. I don't think it was worth the extra money- it was definitely a cute place to stay in the historic town and a unique experience, but thats just how we felt afterwards. I'm sure the man was upset that he could've made more money if we followed the rules and booked two rooms, but we just didn't need two rooms. So, for future St. Augustine visits, just go with a simple hotel that is spacious, fully functioning, and lets you be. 

Day two we headed straight for the St. Augustine Lighthouse! Adult tickets are $12, and this is something we hadn't done since fourth grade so naturally we had to make it our last stop before heading home. The grounds are beautiful, there are trails to walk, small exhibits to see, and an awesome view from the top. Such a fun spot to hit while you're in the area. 

All in all, we plan on coming back every year because of how great our trip was for being an inexpensive getaway so close to home. If you're near St. Augustine, definitely make a point to go and spend some time. You can do everything you want to do in a day and its for sure worth the stop. 

More pictures up in the "Florida" Destination Gallery.

Go With It-