The oldest city in the United States has been continuously inhabited since 1565. St. Augustine is as pretty as it is old, and I could spend whole days under the spell of Castillo de San Marcos or the Colonial Quarter.
More than almost any American city, St. Augustine has a European atmosphere. You can feel it on the narrow lanes, in the historic architecture, and the plentiful museums, all waiting to be explored.
You can find out about medicine in Colonial times, the days of pirates, incarceration, military history in St. Augustine, and the city’s 19th-century rebirth has a distinguished resort.
Five minutes from the historic downtown are boundless Atlantic beaches, and state parks mixing compelling human history with jaw-dropping natural beauty.
1. Castillo de San Marcos
Visiting St. Augustine’s Castillo de San Marcos has always been a real highlight of my trips to the city. This imposing fort was built on the coast by the Spanish in the late 17th century.
In the proceeding century, it would withstand two attacks by the British as they looked to expand south into Florida.
The fort changed hands many times, but still today it stands proud in St. Augustine. One of the beSt. examples of a star-shaped fort in the country, it’s incredibly well preserved.
You can walk along the old ramparts, gaze out across the Atlantic Ocean, and immerse yourself in the city’s colonial history.
2. Colonial Quarter
By the fort, you can visit another of the best things to do in St. Augustine. The Colonial Quarter is a great example of preserved Spanish architecture.
It’s recently been completely renovated as well, in order to preserve this wonderful piece of local history.
Previously known as the Spanish Quarter, you can join tours led by guides in full authentic colonial dress. I recommend these walks if you want an insight into what life was like from the 16th through to the 18th century.
It’s living history at its best, and you’ll see musket loading drills and perhaps even the odd cannon being fired too.
3. Lightner Museum
This attraction is within the opulent walls of the former Hotel Alcazar, dating to 1887. This was a grand Gilded Age resort hotel, built by the railroad entrepreneur, Henry Flagler.
A visit to the Lightner Museum is another chance to learn more about St. Augustine’s extensive history. Moreover, there’s a sublime collection of Gilded Age finery on show.
You’ll come across a strange array of exhibits and artifacts, ranging from 19th-century musical instruments to Native American archaeological finds. You can even find an Egyptian Mummy and a somewhat chilling shrunken head.
What I appreciated most of all was the dazzling 19th-century cut glass on the second floor, with pieces by the studio of Louis Comfort Tiffany, among others.
4. Spanish Military Hospital Museum
Another riveting historical stop is the St. Augustine Spanish Military Hospital Museum. It might seem like a niche subject, but this museum offers an intriguing insight into Colonial medicinal practices.
Browsing the apothecary and watching a re-enactment of an amputation, I was shocked by the crudeness of medicine in past centuries.
I did come away with a newfound appreciation for the wonders of modern medicine and hospitals. There’s a huge collection of preserved instruments, going back to the 17th century.
The building itself is a faithful reconstruction of the hospital as it appeared in 1790, raised on the foundations of the original.
5. Old Jail
If gritty history is your thing though, then St. Augustine has plenty to offer you. Another intriguing historical site to visit is the Old Jail, where you can delve into justice and corrections in St. Augustine.
The jail dates to 1891, and you can join guided tours through the cells that are actually led by actors dressed as inmates. This Romanesque Revival building replaced an earlier structure on the site of Flagler’s Ponce de Leon Hotel.
If you dare, you can even sign up for a nighttime tour. You’ll be led through the gloomy prison and will hear all the worst stories and exploits in the dead of night.
Despite the jump scares, none of this is as terrifying as it sounds, as the tours are done with a lot of wit and historical color.
6. St Augustine Lighthouse and Maritime Museum
To get in touch with the city’s maritime history, take a trip to the St. Augustine Lighthouse and Maritime Museum. The tall lighthouse dates back to 1874 and rises to 165 feet.
I climbed to the top for 360° views along the coast, over St. Augustine, and out over the Atlantic.
Meanwhile the on-site museum offers a wonderful glimpse into local maritime history. Exhibits are wide-ranging, looking at coastal defense in WWII, shipwrecks, the work of marine archaeologists, and the history of boatbuilding in the area.
On the grounds you can wander in a beautiful natural hammock, while there’s also a playground for kids.
7. Cathedral Basilica of St. Augustine
The seat of the first Catholic parish in the United States, people have worshiped at this church for 300+ years.
The current building is a melange of styles, from Spanish Colonial to Renaissance Revival. This is explained by the building’s checkered history, marked by 18th-century abandonment and fires.
The most recent of these was in 1887, sparking a like-for-like reconstruction part-funded by Henry Flagler.
Among the fixtures I admired inside were the stained glass windows recounting the story of Saint Augustine of Hippo, and the radiant gilded lindenwood statuary.
8. Anastasia State Park
Engrossed as I was by St. Augustine’s history and culture, I clean forgot that there’s inspiring natural beauty on the city’s outskirts.
On a peninsula across the bay from downtown, this is a wonderful place to explore, in an area historic and beautiful.
Anastasia Island is where the Spanish mined the coquina stone for St. Augustine. A trail leads you through one of these preserved quarries. Although it’s a low-key attraction, the history is compelling.
On the shore, the state park has four miles of unspoiled beach. This is pounded by the Atlantic waves, with hilly dunes rising behind.
This spectacular environment can be traversed on the Ancient Dunes Nature Trail, where you may see roseate spoonbills, osprey, eagles, and a diversity of other birds.
9. Vilano Beach
I think any visit to St. Augustine has to include some time across the Tolomato River in Vilano Beach. A favored beach getaway for more than 200 years, Vilano Beach is especially prized for its sunsets.
These are best enjoyed from the west-facing Vilano Beach Fishing Pier, jutting into the Tolomato River next to the Francis and Mary Usina Bridge.
On the Atlantic side is a beach at the mercy of the elements, with the best surfing in the St. Augustine area. The easiest public access is Surfside Park, treasured for its shelling, sea glass and sharks’ teeth.
10. Fort Mose Historic State Park
A few miles outside of the city lies one of Florida’s most important historical sites. Fort Mose was built by the Spanish in the 18th century and was initially intended to be a settlement for freed enslaved people.
It was the first settlement of its kind in what would become the United States, as the Spanish welcomed slaves who had escaped from what British colonies to the north.
For Mose a truly fascinating place to visit. Indeed, I found out about a battle that occurred in 1740 between the Spanish—and black militia—and the British, forcing the latter to retreat to Georgia.
To go with its historical significance, Fort Mose is also a natural escape. There’s a kayak/canoe launch, and a birding boardwalk with an observation area.
11. Pirate and Treasure Museum
In St. Augustine’s lineup of historical museums is the quirky but educational Pirate and Treasure Museum.
The first thing I have to mention about this place is how immersive it is. You’ll be dropped right into the 18th-century, at Port Royal, Jamaica.
This is a trove for pirate fans like me, overloaded with artifacts and archaeological relics collected from around the world.
Among the unique finds are a gun that was supposedly owned by notorious privateer Blackbeard, as well as gold stolen by buccaneers and much, much more. Something truly special is one of only three surviving Jolly Roger flags in the world.
12. Ponce de Leon’s Fountain of Youth Archaeological Park
Another worthwhile thing detour in St. Augustine is to explore Ponce de Leon’s Fountain of Youth Archeological Park.
This archaeological site was claimed to be where Juan Ponce de León (1574-1621) landed on the American continent. He was the Spanish explorer who came to the Americas in search of the fabled Fountain of Youth in the early 16th century.
It’s evolved into a rather unusual tourist attraction within the city. And while I know there’s little factual basis behind the park’s supposed archaeological finds, it’s still a unique place to visit. You can even drink from the supposed Fountain of Youth.
13. St Augustine Distillery
For a break from all the museums and historical sites you can head to the St. Augustine Distillery.
This local business produces gin, rum, vodka, and of course, whiskey. They also have an awesome lineup of cocktail mixers.
I loved the setting, in an historic converted ice plant dating back to 1917. You can join a guided tour to see how the spirits are made firsthand, and then enjoy a few samples at the end.
Alternatively, you can make a self-guided visit, checking out museum-style informative signs. These go into a variety of topics, from the transformation of the ice plant, to sourcing ingredients, and the distillation process.
14. San Sebastian Winery
Housed in an historic building constructed for Henry Flagler’s East Coast Railway is one of the state’s premier wineries.
San Sebastian Winery has been around since 1996, and pioneered wines made from Muscadine grapes.
Over the years this company has picked up close to 800 awards, for its Muscadine wines, as well as vinifera wines like Cabernet Sauvignon and Chardonnay.
You can tour through the premises seven days a week. On your way you’ll see how the wine is produced, and will get to sample several varieties.
What really makes this place for me is The Cellar Upstairs Bar. Open only on weekends, this spot has stunning views of St. Augustine, and live music.
15. Black Raven Pirate Ship
If you have pirate-obsessed kids, you’ve certainly traveled to the right place. One of the best things for families to do in St. Augustine is to join a cruise on the Black Raven Pirate Ship.
This is a full-on pirate experience. The authentic replica pirate ship offers an onboard pirate-themed show.
There’s music, drinks, food, singing and dancing, and the crew and entertainers are all dressed up in period costumes from the pirating days.
The whole experience is geared towards wee ones, but there’s enough to entertain parents too.