Considered one of the oldest cities in America, St. Augustine was settled by the Spanish in 1565, long before the English pilgrims settled in Jamestown. I have visited this city many times over the years, and let me tell you, this city has some stories to be told and adventures to be had. Every time I go, I learn new historical facts, hear someone else's story, take in new sights, and try delicious concoctions. Whether you are there for an extended weekend or just a quaint day trip, St. Augustine will have you leaving with memories and stories.
Now first things first, let's talk about logistics, like parking. In the downtown heart of the city, there is very little parking. The good news is most things in this area are within walking distance. Remember, the city was built at a time when you used your own two feet or a horse to get around. But to use your time wisely and give your tootsies a break, I suggest using the services of the Old Town Trolley. A ticket will allow you to hop on and off the trolley throughout the day as it makes its stops. It costs between $35-$40 for an adult and $17-$25 for a child. If you purchase your trolley ticket ahead of time from their website, you can receive a discounted rate. You can also purchase tickets for different tours around St. Augustine at the Old Town Trolley kiosks or their website and receive a discount on certain tickets. There are four locations where you can park and jump on a trolley. Parking is free or less than $10 depending on where you park, with of course purchase of a trolley ticket. Here is a link to the parking locations and a price breakdown.
There are public parking lots around the city tucked away on back streets and behind businesses. You can also keep an eye out for an open spot along the street. But for a more guaranteed option, you can park at the large Historic Downtown Parking Facility. It is $15.00 to park per vehicle.
Now with that out of the way, let's get to talking about all the fun and historic things to do and see.
One iconic and Instagram-worthy thing you can do is get a picture at the original gates to the city.
While you are over on that side of the city, the great Fort Castillo de San Marcos is just across the street. And I know to some, a fort might not seem that exciting, but trust me, you are going to want to see inside those coquina walls.
As you cross the drawbridge and enter the fort, you are transported to another time. They have actors/volunteers walking around in Spanish soldier uniforms from the 1700s who can answer questions and tell you more about the fort and what it was like to live there. As you enter the rooms, you will see displays of artifacts and learn what the space was used for. You might meet one of the actors who can regale you with a story. As you climb to the top of the fort, prepare your eyes for the glittering view of the Matanzas River. On the weekends throughout the day, they have musket and cannon demonstrations. This is a definite must-see if you are visiting on a Saturday or Sunday. They go through the whole proper protocol as the soldiers would have done back in the day to fire a cannon. Warning! It is loud, so be sure to cover your ears!
If you want to take a stroll closer to the water, there is a coquina path just outside the fort.
Whether you are a history nerd like me or someone who believes in legends, a trip to the Fountain of Youth is a must. Now the location of this historical spot is further away from the downtown area, but still a quick trip on the trolley.
The Fountain of Youth is said to be found many places in Florida and possibly all over the world. But this declared fountain was discovered by Ponce de Leon. The water, considered magical for its mineral content, comes from the aquifers that lie beneath the ground. These same aquifers deliver fresh water to all springs. They have a little cup you can grab to catch a drip from the small waterfall and take a sip of this "mystical water."
There is plenty more to do over here than just take shots of water. This spot is deemed the location of the first settlement. Spread across the property are tents and shops brought to life by actors portraying daily life in the 16th century.
Fun fact! September 4th is Founders Day. And on that day, a large parade makes its way down from the park's entrance all the way to the water's edge. You will see Spanish nobility, horses, soldiers, priests, and townspeople all marching in the parade to the beat of drums as cannons fire.
One of the places I was so excited to visit was Flagler College. The building was originally a hotel created by Henry Flagler, an oil and railroad tycoon, for him and his friends on their visits to Florida. I won't spoil too much because I do suggest taking the tour. It is well worth it to learn about the architects, the inspirations for the architecture, and what it was like to be a guest at the Ponce de Leon Hotel.
Right across the street is the Lightner Museum. Once known as the Alcazar Hotel, also owned by Henry Flagler, it was passed into the hands of Otto Lightner in 1948 and became an extraordinary place of collected items. Just to mention a few, you will see William Churchill's lion, Napoleon Bonaparte's desk, and a small ivory carving of the Taj Mahal. I could spend hours in this place!
There is a whole room dedicated to beautiful crystal pieces. I felt like I was inside a diamond!
When my parents came to visit St. Augustine, they wanted to check out the Spanish Military Hospital. I was a little hesitant at first since medical stuff can make me a bit queasy. But it was so cool to learn how advanced these Spanish hospitals were and their knowledge of fruits and herbs. One of the fun facts was they used a lot of lavender, which is a natural antiseptic and also calming to those sick and injured.
A fun place to visit for all ages is the Pirate Museum. Located a short walk from Fort Castillo de San Marcos, this immersive and interactive museum teaches you about the real pirates of the Caribbean. You even have the chance to go on a scavenger hunt for clues that will lead you to chest of treasure.
Finally, on my most recent trip to this historical city, I got to visit the St. Augustine Lighthouse.
To visit this historical landmark, you will cross over the famous Lion Bridge to Anastasia Island.
While the lighthouse is the main attraction, you can also visit the lightkeeper's house, the WW2 Coast Guard Quarters, and the building where they conduct shipwreck artifact research. I visited around the holidays so they had the main house and the lighthouse all decked out in wreaths, lights, and Christmas bows. If you want to climb the iron staircase to the top of the lighthouse, it is 219 stairs/14 stories.
The view is totally worth it, and there are landings with a bench if you need to take a break.
They do have ghost story tours at the lighthouse that they conduct in both the daytime and at night. They weren't operating due to the special Christmas light tour offering they had, but I did get one of the volunteers to tell me a tale. I won't spoil the story if you decide to take the ghost tour, but there have been sightings of wet barefoot prints at the top of the lighthouse...
A detour away from all the history and ghost stories, let's have a drink! Near downtown St. Augustine are San Sebastian Winery and St. Augustine Distillery. You can drive and park in the parking lot or nearby. Or you can also reach this destination by trolley since they stop at both locations.
If you have visited Lakeridge Winery in Orlando, San Sebastian Winery is the sister company. Their wines are mainly composed of the muscadine grape, which tends to be sweeter. They offer a free tour and tastings of all their wines. I enjoyed the tour at the San Sebastian Winery more because they had a little bit more selection-wise, and I enjoyed the aesthetics of the building inside, with stone walkways and peaks into the barrel rooms. You will end at the gift shop where you can purchase their wine and other accouterments for your next wine night.
Again you can pop over to the St. Augustine Distillery by car, foot, or trolley. They have a free tasting tour as well. Now you don't get to go on a fun journey throughout the property as you do on the wine tour, but our tour guide/bartender was charismatic and gave us a good pour of each liquor. You will exit the tour at the gift shop where you can buy their products. I loved the vodka that I tried because it didn't have the strong burn feel on the back of the throat like a vodka can. Fun fact! Their vodka is made with sugar cane. Attached to the distillery is their bar and restaurant called Ice Plant. The cocktails are superb!
The main avenue that guides you through the heart of the city is St. George Street. This is the main thoroughfare with tons of shops and restaurants.
I always enjoy visiting the Pelindaba Lavender store. They have tons of products for beauty, cooking, and household cleaning. And who can't resist grabbing a sweet treat from an old fashion candy store like Savannah Sweets.
Before we discuss food options, let's talk about coffee places. Whether you need something to get you going in the morning or an afternoon pick-me-up, a good cup of joe is important.
This first place is not in the heart of the city, but it is a good place to stop if you are on your way there. Coffee House Realty Cafe is located in an adorable blue southern colonial-style house. Theo and Diane Glorie are the owners of this little coffee house. Theo is also a realtor for the area, and they are artists. You can see and purchase their paintings that decorate their already colorful walls. If you desire a delicious cup of coffee surrounded by a warm ambiance, they got you. They also have a case of homemade treats like loaves of bread, croissants, and muffins. I got the Viennese coffee, Diane's favorite, and a slice of her homemade coconut tres leches.
Here are some other coffee shops to check out near the heart of St. Augustine. Crucial Coffee Cafe, which is in a small wooden cabin, and The Kookaburra Coffee located inside the elaborate Mediterranean Revival building 24 Cathedral Place, also known as Treasure on the Plaza. Kookaburra is an Australian bird, befitting this Aussie-American coffee bar.
Now let's discuss dining options.
If you are looking for a relaxed lunch vibe that is family and kid-friendly, I suggest the Florida Cracker Cafe. They have a good home cookin' menu. I suggest the Minorcan clam chowder (a St. Augustine/Jacksonville local favorite you can find at many of the restaurants) and the Florida Cracker Po'Boy. There were so many yummy options to order, but I wanted to save room for other treats later. I got a side of grits with my sandwich, and as someone from Texas, I judge grits quite harshly. And these grits were perfection!
The Floridian is the perfect place to have an elevated lunch or a casual dinner. The decor and vibe tie in perfectly with the name. The food is southern seafood full of flavor done to an elevated level. Their drinks are full of flavor and named with a fun Floridian twist. I'm a fan of mezcal, so I suggest the "No Country For Old Men," but you will enjoy any drink from the tiki bar.
At the restaurant Preserved, I had one of the best meals I have ever had in my life! It is located in the neighborhood called Lincolnville, which is a few blocks south of Flagler College. It is located in the cutest blue and white southern Victorian-style house with a wrap-around porch. The food is southern with a French flair. I highly suggest getting the mussels and the charcuterie board! It's not your average charcuterie board. One of the components is duck prosciutto. The full experience, from food to service to the ambiance, was excellent!
Another upscale and quaint dining option is Catch 27. This restaurant is located a few blocks over from bustling George Street on a quiet avenue. They have seating inside and outside with a patio garden. They specialize in a contemporary fusion of southern and seafood dishes. Their drinks are expertly layered with fragrant notes and appetizing flavors, and this is one of the few places that have mocktails.
Other restaurants that I haven't been to (but plan to visit) and come recommended by friends are:
Sangrias Wine and Tapas Bar
Columbia (the original one is in Ybor City)
One of the biggest events that happen every year in this city is the Night of Lights. Most of downtown St. Augustine gets completely decorated with Christmas lights. You can view these lights by walking around or you can take the special trolley tour. To book the Night of Lights Trolley Tour with the Old Town Trolley, you can purchase tickets on the website or at one of the kiosks. These tickets are a little different than daily trolley tickets. One ticket purchased is for one row in the trolley (which can hold up to 4 adults). The tickets can range from $69-$89, depending on how far out you book and what time slot you choose. With the purchase of a ticket, you will receive a complimentary cup of cider and a cookie for each person in your party. They used to give it to you before you got on the trolley, but now you don't receive your treats until after your holiday ride through the lights. While you take in the twinkling glow of the city, Christmas music will be playing to fully envelop you in holiday cheer. The Night of Lights begins mid-November and continues through the end of January.
In the oldest city in America that holds so many stories, I encourage you to go and write your own page.
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