We had many friends tell us how amazing St. Augustine was. A little town right on the east coast of Florida in between Daytona Beach and Jacksonville. I’d driven by in dozens of times over the last few years, but had never made the time to check it out.
I’ve said it before and I’ll say it again, this pandemic has forced us to travel more locally and we are absolutely loving it so far. There is so much history in our backyard!
Quick History
The historical city of St. Augustine was founded in 1565 by the Spanish, 42 years before the English colony at Jamestown, Virginia was established and 55 years before the Pilgrams hit Plymoth Rock, Massachusetts[1]. The architecture is rich with Spanish Renaissance vibes and there are many historical buildings and sites to explore.
Quick tip: Try and find a hotel or Air BnB that is within walking distance of the Colonial Quarter. This is the hub of the town and will make for lots of good exercise!
[1] https://www.oldcity.com/history-and-culture/
Day 1: Arrived at 4pm
When we landed on day one, we wanted to go exploring. We took a walk through the Colonial Quarter down St. George Street. This cobble stone street has tons of mom & pop shops and restaurants and really shows you the uniqueness of this town.
Drinks: Sangria’s Wine & Tapa’s Bar – we had someone recommend Sangria’s so we wanted to give it a try. This fun spot has a second-floor balcony that led to the ultimate people watching adventure. Plus, the sangrias were amazing of course.
Fun fact: there is a small square garden that you overlook while sitting at Sangria’s. After a little research we found out that land is still owned by Spain and you actually need a passport to go through the gate!
Dinner: Harry’s Seafood Bar & Grille – This was such a blast. Cajan style food, live music, and a ridiculous outdoor patio. Our server was incredible as well! Highly recommend this spot.
Brewery: Ancient City Brewery– We are suckers for a good brewery and landed at this one right around the corner from Harry’s. A low-key spot with high-quality beers. We saw their beers on taps all around the city, but I was exceptionally fond of the Anastasia Island IPA. Light but hoppy and easy to drink.
Day 2
Breakfast: Schmagel’s Bagels – This was such a great little spot with lots of shaded tables to sit outside. The menu was deep including multiple types of bagels and spreads as well as more robust breakfast sandwiches. Highly recommend!
Museum: Villa Zorayda Museum – Jackie’s pick for the day was this museum built in 1883 as a winter residence for Franklin Webster Smith. The walls and rooms are filled with an incredible art collection from around the world and the structure itself is a unique art piece. It has also been a casino, a speakeasy, and a restaurant. In 1933 it was turned into a museum. We really enjoyed it!
Tour: Whetstones Chocolates – Mandy’s pick was (obviously) a chocolate tour at boutique Whetstone’s. They walked us through how chocolate is made and we got to taste so many types of chocolate! Pro tip – try to gelato at the end of the tour!
Lunch: Ice Plant Bar – everyone, and I mean everyone, recommended this place and we know exactly why. Unbelievable drinks, killer food, and it’s right next to the St Augustine Distillery so you can plan to take a tour after lunch. It was an actual Ice warehouse originally (hence the name) and blocks of ice would be made and then put onto boats to keep fish cold. Definitely a great vibe all the way around.
Historical Stops: Due to COVID, a lot of spots were closed for tours. But we were able to walk by Flagler College – originally the Ponce de Leon hotel built in 1887 – and admire it’s architecture. We also saw the Lightner Museum, another former hotel named Alcazar built in 1888, and known for it’s wealthy guests who would visit in the winter.
After a much-needed nap, we headed out for dinner and a ghost tour. Considering it’s America’s Oldest City, there is definitely some spooky things that have happened in this town. We did the Secrets of St. Augustine Ghost Tour with Dion Moore. Dion was extraordinarily knowledgeable and we had a blast learning about the 450-years of spooky stories. Highly recommend! [View & Book Tour Here]
Day 3
We brought our bikes, but there are a few places you can rent them around town. We loved seeing the town by bike and really enjoyed covering more ground without being in the car!
Breakfast: Blue Hen Café – this cute spot was recommended by our Air BnB and after eating there, we know why! Obviously freshly made that day, we loved this little local spot. (Get the biscuits!)
Historical Spot/Museum: St. Augustine Lighthouse/Maritime Museum – We biked about 2.5 miles to the infamous lighthouse and museum. We loved walking the beautiful grounds and learning more about the history. Apparently, they have their own ghost tour which we planned to do next time as well. Jackie took the 219 steps up to the top, but Mandy’s fear of heights kicked in about half way up. Either way, fun adventure!
Lunch/Cocktails: Odd Birds Cocktail Lounge & Kitchen– Since this spot was over the bridge, it was the perfect time to stop and cool off with a great cocktail. The civeche was so light and refreshing, we loved the hipster vibe as well.
Historical spot – Castille de San Marcos – Due to COVID restrictions we couldn’t go inside the fort, but we were able to walk around the outside this 315 year old fort. The stone fortress is right on the water and has plenty of spots to sit and enjoy the breeze. Worth checking out!
Wine Stop – San Sebastian Winery – Being on our bikes allowed us to zigzag all over town, so with some time in the afternoon we headed over the San Sebastian Winery for charcuterie and wine. Their rooftop deck and live music made for the perfect afternoon. Plus, they surprised us with a glass of champagne when we mentioned we were planning a wedding!
After another much needed nap…
Dinner: Catch 27 – we cannot say enough good things about this spot. The staff was incredible, the drinks were amazing and the food was fresh and unique. If you are a seafood fan & also enjoy a good cocktail, this is a must try. We both picked this as our favorite spot for the weekend and would absolutely head back!
These three days were packed full of good food and historic spots. There is plenty we didn’t have time to check out such as the Old Jail, the Fountain of Youth, and the Pirate tours. Plus many more restaurants, of course! Overall, we would highly recommend St. Augustine for a great 3-day trip!
Cheer’s to Chasing Our Compass!
