May of 2021 Michael and I took a trip to St. Augustine together and had the most incredible week! This was our first time on a flight together and our first time treating ourselves to a full week away. We were very excited to have the opportunity to escape for the week because Michael had just started working full time the January prior but had the option to work virtually, and my classes were still mostly through zoom. Because of this, I actually got to complete some of my final exams poolside.

We did a lot of exciting planning beforehand to fit in everything we wanted to do on our trip. We used a website called Wanderlog to make our itinerary, and we used Atlas Obscura (more to come in a future post) to find some hidden gems that we were excited to see. This is how we learned about the legend of the St. Augustine Love Trees and the promise that any couple that kisses under them will stay together forever.

The Love Trees of St. Augustine

Wanderlog kept track of everything for us. We flew Delta, our go-to airline, and we stayed at the La Fiesta Ocean Inn & Suites, which had a mini golf course next door. The Fiesta Falls mini golf course is where we ended almost every day (I won 2/3 games!!!).

I wanted to go to St. Augustine for a getaway that was more than just a beach trip because I had gone to Cocoa Beach not long before. St. Augustine is the oldest city in America, and it has so much to offer, from its sunny beaches to its beautiful culture packed downtown.

Our First Night in St. Augustine

Our flight went great. We arrived early to the airport and grabbed a snack before getting on the plane. We flew Delta, our go-to airline, and even landed before schedule. Unfortunately, the rental car was a whole different story. It took over an hour for them to get us our rental car, and then we made the 45 minute drive to our hotel. We were starving by the time we got there at almost 1am. We decided to order from the only place still open, Five Star Pizza. Luckily, despite being two New Yorkers, we’re not snobby about our pizza. We absolutely love pizza joints like Domino’s and Papa John’s, so Five Star was just what we needed.

When we got to our room, Michael went to our office and checked us in. He came back and surprised me with chocolate and champagne. He had ordered it with the room. I’m not sure if you guys have done this, but if the hotel you are staying at has a package like this, add it. It was so romantic when we got to share it on the beach together the next night.

Exploring St. Augustine’s Best Attractions

The St. Augustine Alligator Farm was so much fun. We zip lined and made our way through obstacles 35 feet over countless reptiles. Then we got to walk through the farm and see the biggest crocodiles I had ever seen, as well as other fun animals like huge tortoises and colorful birds.

I also took my first surfing lesson while in St. Augustine. It went great. I even saw a baby dolphin swim by as I was trying to figure out how to balance on my board without tumbling into the waves.

St . Augustine has a rich history, so we made sure to get a taste of that too. We made it to Castillo de San Marcos, Ponce de Leon’s Fountain of Youth, and the St. Augustine Pirate & Treasure Museum. The Castillo de San Marcos is really cool to walk around and gives you a beautiful view of the water. We didn’t even feel the need to go inside, however you can if you’d like to. Definitely great to do on a day with nice weather. The Fountain of Youth is worth dedicating a little more time to. The park is dedicated to sharing native and conquistador history. We ate a delicious hot dog and shared a cup of sangria served to us by a very grumpy counter girl before entering the park, which was full of peacocks. The Fountain of Youth is located right after the entrance, and we made sure to take a sip before exploring around. We definitely advise talking to some of the staff in the park; they had a lot of fun facts to share. Definitely stay to watch the show at the far end of the park. They shoot off a real cannon, which was louder than we could have imagined, and send a projectile further than our eyes could follow. The park also had a beautiful dock on the water, and we saw a manatee swimming around! Lastly, we visited the pirate museum, where we got to complete a treasure hunt as we explored the displays. We got to pick a prize once we found the last hidden clue.

I’m not a big history person and don’t typically love museums, but I had a great time exploring all three sites. 🤗

St. Augustine’s Yummiest Foods

St. Augustine had a ton of great food and drink options! Our hotel had a delicious breakfast included that they brought to our room every morning. Warm sausage and egg sandwiches on croissants, delicious scones, and lots of yummy yogurts and juices! We found so much great food without even leaving St. Augustine Beach. On our second day, we discovered our favorite lunch spot, the Beachcomber. We couldn’t wait to order our mid-day drinks at their tropical bar. Every day we saw locals and their fluffy friends enjoying their lunch at the brightly colored picnic tables with their toes in the sand. The blackened fish of the day sandwich with a strawberry daiquiri was just perfect. After our first visit, we couldn’t stay away!

Mango Mango’s and the Burrito Works Taco Shop were also great spots for a casual bite. Mango Mango’s had a cute family feel with indoor seating, delicious summery drinks, and the teriyaki chicken kabobs alone were enough to make the visit worth it. The Burrito Works Taco Shop had fun live music and cozy outdoor seating where we enjoyed our huge, tasty burritos.

Our hotel was in St. Augustine Beach, but we made it to downtown St. Augustine most nights. We ended up at Forgotten Tonic on our first night out. It was one of the only spots without a wait. What great luck, because it turned out to be awesome! Right when we arrived, our waiter made us feel welcome. He helped us pick out a fun-sounding drink (the Bee’s Knees!), and he told us where to find all the best bars uptown. The Bee’s Knees was the perfect choice, and now it’s our absolute favorite drink! We ordered a bunch of appetizers to share, and they were all delicious. When we left, we already felt excited to make it back here the night of our bar crawl later in the week. Prohibition Kitchen was also a great meal, but definitely make sure to go on an empty stomach! Best burgers ever!

21 in St. Augustine

Turning 21 during quarantine set us back in terms of learning about our favorite drinks. St. Augustine was a fun opportunity to explore. We shared lots of fun drinks of all kinds and found all of the best little spots to grab a drink, and St. Augustine had a lot. The bars had fun specialty options that were fun to taste, and for the most part, delicious.

Here were some of our favorite drinks we got to try, if you have the chance you should definitely try them too!

Aperol Spritz: I was looking for a new go-to drink I could order and enjoy at any restaurant so I gave this one a try, and loved it! An Aperol Spritz is a mixed drink made with Aperol (a bitter tasting Italian liquor), Prosecco, and a splash of soda water.

Bee’s Knees: I know I mentioned this one earlier, but it deserves another shoutout. The Forgotten Tonic put lavender in theirs, which was a really nice touch. Typically, a Bee’s Knees is a gin and tonic with honey.

Purple Lollipop: From the Milton Tavern, this drink was delicious if you love sweet drinks. Really sweet drinks. It was made with Smirnoff Grape Vodka, Grenadine, Blue Curacao, & Lemonade. And they even served it with a lollipop. 🍭

Our 2021 Florida Trips

We loved St. Augustine so much that when we started talking about where we might buy our first home together in was one of our top choices. A few months after our St. Augustine trip we made our way to Miami and had another incredible trip. Click here to read about that trip, and click here for all of our posts about our travels.


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