Weekend Guide To St. Augustine

A couple weeks ago, Joe and I spent the weekend in St. Augustine, so I figured I’d share a few highlights from the trip.

We stayed at the Casa Monica, a beautiful Moroccan-themed hotel that I highly recommend. It was a  little pricey, but Joe had a bunch of Marriot points accumulated and we able to use them which saved us a ton.

Anyway, we drove up from Miami Saturday morning, and arrived in St. Augustine at around 2pm. After we had checked in and put all of our bags away, we headed into town and started exploring!

We honestly had such a great weekend despite the terrible weather, but these were some of my favorite things we did during our trip.


Unless you’re hitting up all the tourist attractions or spending all of your money at boutiques, there really isn’t a whole lot to do in St. Augustine other than eat and drink – something I’m 100% ok with.

Prohibition Kitchen


Apparently this is a fairly new restaurant, but you wouldn’t know it based on the fact that it’s always full. But as soon as I walked in, I could see why. It’s got that whole prohibition-era vibe to it, and the food is delicious. Giant pretzel with beer cheese? Um…amazing.

Cap’s On The Water


If you’re looking for a good view, this is where you want to be. Joe and enjoyed the most delicious and relaxing meal while watching the sunset and everything about the ambiance here was on point. I had the best mahi-mahi I’ve had in a long time, making the Uber ride there completely worth it.



We did the Sunday brunch at Raintree and it was really nice. I felt like I was walking into a little bed and breakfast, which coming from a big city was so refreshing. The staff was super friendly and my omelette was just what I needed. Plus, I think the majority of the breakfast options come with access to the breakfast buffet, which includes fresh fruit, pastries, grits, and some sugar cookies I was a bag fan of.

Meehan’s Irish Pub


The hubby wouldn’t have let me leave St. Augustine without going to Meehan’s because that’s where they serve Kilkenny. He has a ridiculous obsession with this beer, and since he can’t find it in Miami, he has to have it every single time he’s in St. Aug. Now I’m not a huge beer drinker, but put a food menu in front of me, and I’ll find something to try. So that’s what I did while he had his drink and let me tell you something, I had the most delicious flat bread pizza thing I’ve ever had. At an IRISH PUB! Shocking, I know. I’ll definitely be back just to have that.

Ice Plant Bar


Ok so I didn’t actually try the food here, but this is one of Joe’s all-time favorite bars. It’s honestly one of the coolest establishments (no pun intended) I’ve ever been in, and their cocktails are AMAZING. Don’t leave St. Aug without having a drink here.


During the few hours that Joe and I weren’t eating or drinking, we did do a couple touristy things that I’d recommend you check out.

Old Town Trolley Tours


First things first, hop on the Old Town Trolley and take a tour of the entire town. We did this on our second day, but if I could do things over again, I would have taken it as soon as we arrived. It’s a great tour that teaches you so much history and it takes you around the whole city while letting you hop on and hop off as much as you’d like. I learned a lot about Henry Flagler and also loved that our tour guide pointed out the very street where Martin Luther King Jr. held some historic marches.

Castillo De San Marcos


It was raining the day we visited the fort meaning we weren’t allowed on the top deck, but it was still super interesting to experience. Given that the fort’s construction was completed in 1695, there’s tons of history there that you can read about as you tour the structure.

Fountain Of Youth


Yes, I drank the water, because hey – if it works, it’s cheaper than Botox. But that wasn’t my favorite part. I honestly just enjoyed walking around the property because the park’s grounds are absolutely stunning. And if you like peacocks, then this is the place for you…have you ever seen one this pretty?


The Old Jail


The Old Jail is a total tourist attraction, but it’s actually really interesting. The tour walks you through the jail that served the city of St. Augustine from as early as 1891, so yea, my money’s on the fact that it’s legitimately haunted.

San Sebastian Winery


If you’re a big wine-o like me, then be sure to stop by the San Sebastian Winery. They offer free wine tastings anytime while they’re open, so you’ll get to grab a little cup and sample a few of their different wines.

So yea, those are just a few of the highlights from our trip. I gotta say, St. Augustine is an extremely charming city, and we’ll certainly be back!

How about you guys? Has anyone been there before? If you have, what are some of your favorite things to do? 


  1. Rubi Mancilla

    June 1, 2017 at 10:18 am

    I love taking Old Town Trolley tours wherever I go! I’m visiting Miami for the first time this summer, but St.Augustine is second on my list.

  2. Jessica @ Polka Dotted All The Things

    June 5, 2017 at 1:57 am

    That pretzel is amazeballs. What a great trip you had.

  3. Rebecca @ Strength and Sunshine

    June 5, 2017 at 3:57 pm

    My mom just took a trip down there in February! So jealous!

  4. Rachel

    June 5, 2017 at 9:12 pm

    Love, love, love St. Augustine! My aunt has a place super close so I’ve never stayed in any of the hotels here, but I definitely need to check some of these places out!

    Rachel / http://www.helloher.co

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