This past weekend, I took the 3.5-hour trip north for a friend’s reunion in St. Augustine, FL. Visiting America’s oldest city with some of my oldest friends seemed fitting. Here is everything we did for our long weekend trip from Friday – Sunday.
Friday
We left the Tampa Bay area around 10am for our 3.5-hour drive. My best friend from college, Aly met me from her house in Naples so we could ride together and spend some great quality time catching up.
We arrived to our Airbnb around 3:00pm after a stop for lunch and a quick trip to the outlet mall, because someone forgot a coat and it was a rare winter weekend in Florida.
Once we arrived to our cute bungalow Airbnb that was conveniently located a short 10 minute walk to old town, we spent some quality time catching up with our two other college friends who joined us for the weekend.
Our plan for Friday evening was to get take-out while getting ready for a night out on the town; it was very much reminiscent of a night out when we were all in college in Miami together.
We got takeout from Mojo’s Tacos and I have to admit it may be the best taco I have ever had. It is a local’s spot and I highly recommend you visit next time you are in St. Augustine.
After stuffing our face with tacos we went out to a few bars in Old Town. The highlight for me was actually our first stop, Colonial Oaks. This outdoor bar had a live band and people were having so much fun singing along and dancing near the stage. Another great stop I highly recommend you add to your list.
After closing down the bars we headed back to our Airbnb, via golf cart. There are plenty of people out trying to make a quick buck that will drive you back. We were more than willing to pay to avoid the 10 minute walk in 20 degree weather. Us Floridians were not prepared for this winter freeze.
Saturday
After sleeping in we finally got up and got ready and started to walk to old town for lunch and to explore. On our walk we stopped into a few cute boutiques along San Marco Ave. Although this is outside of the true tourist destination I do recommend walking to these unique shops and antique stores.
Also, along San Marco Ave, we stopped at the Itty-Bitty Donut Shop for a snack. These are mini donuts with unique and special flavors.
After walking around the Fort and Old Town we ate lunch at The Floridian. This restaurant has a unique menu and even more unique drinks. Be sure to ask about the story of the Swamp Donkey!
Then we walked over to the St. Augustine Distillery to do a free tour. This a great way to try some of your favorite liquors and try some new ones. The Gin and Toxic was a good surprise to me. After the tour we walked up to Ice Plant, the popular bar and restaurant that shares space with the distillery. I can’t recommend Ice Plant enough. The drinks were AMAZING and while we didn’t eat there all the food coming out of the kitchen looked delicious.
To wrap up Saturday we went to Harry’s, a very popular restaurant in Old Town. Since they don’t take reservations we waited over an hour and a half for a table. But that didn’t bother us. We sat at the bar, had some wine and appetizers and continued to enjoy each others company.
Sunday
Since we all wanted to get out on the road early we decided to do a quick breakfast before heading out. We went back to Old Town and had a great breakfast at Maple Street Biscuit Company. What is so fun about this spot is that instead of getting your name for your order they have special questions and your answer is what they call when your food is ready. My question was “What one item would you bring to a deserted island?” Fittingly my answer was wine.
Overall while we didn’t do much more than eating, drinking, and a little bit of walking around it was so nice to just catch up with old friends. The weekend was fun and relaxing and I can’t wait till the 4 of us do another trip!