I first learned about Florida’s St. Augustine Historic District during the pandemic when articles were coming out about places to visit in the United States that would give you a European feel. And I knew I needed to check it out. This small town was founded in 1565 by the Spanish making it the oldest continually-inhabited European town in America. St. Augustine has a ton of history with structures that date back hundred of years. However, history isn’t the only thing going for this town. Keep reading for all the things in St. Augustine to keep you busy for a weekend getaway.
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When Should You Visit St. Augustine Historic District
Anytime is the short answer, but each season has its own reasons to visit St. Augustine Historic District. The best weather for meandering around town is in the Spring and Fall when the temperatures are the most pleasant. While Summers can be hot and humid, you can cool off at the nearby white sand beaches. Winters in Florida can be mild or they can be extremely cold, so it is a little bit of a risk to travel during this time. However, winter events such as Night of Lights and Colonial Night Watch may be worth braving the cold temperatures.
How to Get Around St. Augustine Historic District
Jacksonville International Airport (JAX) is the closest airport to St. Augustine and is located approximately 45 minutes north of town. The cheapest way to get to St. Augustine from the airport is by bus, but it is also the least convenient. I recommend renting a car and making the drive, especially if you want to drive around town.
Once you are in town, you can walk, rideshare, drive, or take the trolley. There is metered parking around town as well as a parking garage that costs $15 a day. We decided to get a 2-day pass for the Old Town Trolley Tours and use this hop-on / hop-off trolley as a means of transportation in the city. The best part is the trolley driver doubles as a tour guide giving interesting information about the history of the town.
Where to Stay in St. Augustine Historic District
We stayed at Holiday Inn St. Augustine on the outskirts of the St. Augustine Historic District. This hotel was close enough to walk to the center of town, but far enough away that it was one of the cheaper hotels to stay in. Also, nearby budget options are Days Inn by Wyndham and Double Tree by Hilton. Inside the historic district are many bed and breakfasts and other hotels that are a little more pricey, but very convenient.
What to Pack for St. Augustine Historic District
- Bug Spray – Mosquitoes can be super annoying so, I highly recommend bringing some bug spray.
- Sunscreen – Protect you skin.
- Chapstick – Keep your lips moisturized with this chapstick with 15 SPF.
- Water Bottle – Stay hydrated with this durable 32-ounce water bottle.
- Crossbody Purse – I carry this crossbody purse when I travel. It is not too big but big enough to hold a water bottle and souvenirs I buy along the way.
- Sunglasses – Shield your eyes with these men’s and women’s sunglasses.
- Cute Sundress – Look chic while meandering the historic district. Here is another dress option.
- Casual Outfit – For a more casual look, try these shorts, jeans, and top.
- Walking Shoes – Make sure to bring comfortable men’s and women’s walking shoes.
Day 1 – St. Augustine Historic District
8:00 AM: Maple Street Biscuit Company
Start you morning off with a bang at Maple Street Biscuit Company which was featured as one of the Food Network’s best places to eat in Florida. I recommend ordering the Squawking Goat which is a homemade biscuit with fried chicken, goat cheese, and pepper jelly. Two pirates were eating breakfast at a table near us, which we thought was a little odd. Turns out, for St. Augustine Historic District, this is not odd at all. Be prepared to see pirates living their lives all over the old city.
9:00 AM: Castillo de San Marcos
Castillo de San Marcos was built by the Spanish to protect its claim on Florida and the Atlantic trade route. Construction began on the Castillo de San Marcos in 1672, making it the oldest masonry fort in the United States. Now, as a national monument, you can enter the fort and see for yourself how life of a soldier was lived back then. Capacity is limited, so make sure to arrive at this attraction first thing in the morning. Tickets to enter are $15 per adult, children (15 and under) are free if they are accompanied by an adult. As part of the National Park System, you can enter at no cost if you have a valid America the Beautiful Interagency Pass. Admission to the park is from 9am to 5pm everyday.
10:30 AM: Ride the Trolley
After spending over an hour exploring Castillo de San Marcos, we hopped on the trolley and decided to ride it through most of the stops. We wanted to hear about some of the history of the St. Augustine Historic District without being interrupted by hopping off at a stop. I am glad we did this, not only to get a history download, but to get a lay of the land.
11:30 AM: Whetstone Chocolate Factory
We finally decided to hop off the trolley at one of the last stops at the Whetstone Chocolate Factory. Our plan was to take a chocolate factory and tasting tour. Unfortunately, we were a couple minutes too late for the tour so we just loaded up on chocolate in the gift shop. See their website for current store and tour times.
12:00 PM: St. Augustine Distillery
Originally, we intended to skip the St. Augustine Distillery tour to do a wine tasting at San Sabastian Winery. However, our trolley guide informed us that their wine is made of muscadines. We had recently traveled to northern Georgia where the local wine was also made of muscadines, and we were not fans. But if you have never tried muscadine wine or if you are a fan, you can check out San Sabastian Winery and their complimentary tours. They are open from 10am to 5pm Monday to Saturday and 11am to 5pm on Sundays.
Even if you do decide to visit the winery, you should also make time for the St. Augustine Distillery. This self-guided tour allows you to sample 5 different cocktails for free! The cocktails are made from their homemade liquors and mixers. You can purchase their liquors and mixers in their gift shop which is conveniently located at the end of the tour.
1:00 PM: Cathedral Basilica de St. Augustine
After visiting the distillery, we hopped back on the trolley to the St. George Street stop where the Cathedral Basilica de St. Augustine is located. We explored the inside of this Spanish church for a short while before walking down St. George Street.
1:30 PM: Prohibition Kitchen
It is definitely time for lunch! We stopped in at Prohibition Kitchen for lunch and delectable drinks. Be prepared to wait a while for a table, but maybe you will luck out with seats at the bar like we did! This place will take you back to the roaring 20s. For a wilder time, come after 9pm when the restaurant turns into a bar with live music.
3:00 PM: Shopping in St. Augustine Historic District
We spent the rest of the afternoon shopping and exploring the St. Augustine Historic District. The old city is full of souvenir shops and boutiques complete with local art and homemade goods. While walking around made sure to find the Old City Gate and the Oldest Wooden Schoolhouse. As a bonus drinking opportunity, visit City Gate Spirits, for free cocktail samples.
7:00 PM: Pelican’s Landing
We ended our night with dinner, drinks, and live music at Pelican’s Landing. This local hotspot also is a great spot to watch live sports.
Day 2 – St. Augustine Historic District
8:00 AM – Georgie’s Diner
We filled our bellies with a large breakfast plate at Georgie’s Diner. This diner will make you feel like you are eating breakfast in the 1950s and has an authentic diner feel with its red booths and checkered tile flooring. The traditional breakfast food items are cooked to perfection.
9:00 AM: Old Jail
After breakfast, drive to the Old Jail, which also happens to be Stop #1 on the Trolley Tours. Here, you can take a tour of the Old Jail which was in operation from 1891 to 1953. Tours of the jail happen every 20 minutes and consist of tales of the prisoners from its past. The jail is open 9am to 4:30pm. Tickets for adults are around $15 and around $9 for children, aged 4-12.
10:30 AM: Colonial Quarter
We went back and forth on whether to visit Colonial Quarter, thinking it may be geared towards children. We finally decided to give it a try, and I am glad we did. It was very interesting. A tour guide gives you a look back in time to see how metal products were made by blacksmithing. They gave you an up close views of what soldiers wore and carried during those times and what a typical house of those times looked like. In addition, the guide fires a live cannon! You can also see views of the city atop the 35-foot watch tower. Tour times are 10:30am, 12pm, 1:30 pm, and 3pm. Tickets are $14 for adults (ages 16 and over) and $8 for children (ages 5-15).
11:30 AM: St. Augustine Pirate & Treasure Museum
The St. Augustine Pirate & Treasure Museum was another activity we were not sure about since we were not traveling with kids, but it was very entertaining. I am not a big museum person, but this museum was interactive, so that kept my attention. When purchasing your tickets, make sure to get a treasure map for the museum. If you do all the tasks on the map, you are rewarded with a piece of treasure! This activity is probably meant for kids, but I had fun doing it!
12:30 PM: Flagler College
One of the most famous landmarks of St. Augustine is Flagler College. The school was built to resemble old Spanish architecture keeping in the theme of the city. Do not be fooled by its Old World architecture though; this school was built in 1968.
1:30 PM: Tini Martini
After a hectic morning, we decided it was time for lunch. In the past 2 days, we frequently passed the Tini Martini Bar and were intrigued, so we ate lunch here. And of course sampled some of their many martini flavors! Some of our favorites were the Key Lime and White Chocolate martinis.
4:00 PM: Beach Time
After a very eventful couple days in the St. Augustine Historic District, we decided to have some downtime on the beach. So we drove down A1A Beach Front Avenue until we found a parking lot with beach access. As we walked along the beach, we were lucky enough to spot dolphins swimming in the surf!
7:00 PM: A1A Ale Works
We ended our weekend in St. Augustine with dinner and drinks at A1A Ale Works Restaurant & Taproom. The food here was amazing, and I highly recommend you get the Key Lime Shrimp and Lobster Linguine. As I am writing, my mouth is watering thinking about that amazing pasta dish!
This concluded our 2 days in the St. Augustine Historic District. After waking up the next morning, we headed back to Jacksonville to catch our plane back home. This was a super fun small town, and it is a town I would visit again and again.
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