17 Unique Things to Do in St. Augustine, Florida

In St. Augustine, Florida, labels like “first” and “oldest” are quite common. It’s the nation’s oldest continuously occupied city, after all, having been founded in 1565.

But the rich history isn’t the only reason tourists flock to St. Augustine. As I discovered, the city also has its fair share of oddities and quirky attractions.

unique things to do st augustine

The most unusual and unique things to do in St. Augustine include walking the narrowest street in the U.S., ziplining over alligators, visiting old medical museums, and viewing artwork so small that it fits inside the eye of a needle.

Not to mention Ponce de Leon’s famous Fountain of Youth, which is (maybe) a real thing.

Read on for a list of our top St. Augustine suggestions, ranging from historic sites to unique museums!

Get Locked up in the Old County Jail

Can you imagine a prison that was built to look… pretty? Well, this one was.

When Henry Flagler contracted the P.J. Pauley Jail company to build the Old St. Johns County Jail, he made sure the building wouldn’t end up being an investment-deterring eyesore.

The result was a charming Victorian-looking hotel. The inside, however, wasn’t so charming—iron-barred cells, creepy gallows, and a death row cell.

Today, you can put yourself in the inmates’ shoes as you tour the old jail. That’s right — not only will you see the prison and hear its harrowing tales, but you can get the actors in period costumes to “book” you as an inmate!

Bonus Fact: The Pauly Jail company later built the infamous Alcatraz prison in San Francisco!

Peek Into the Hidden Dungeon at the Oldest Wooden Schoolhouse

oldest schoolhouse

Over the years, St. Augustine’s Oldest Wooden Schoolhouse was used as a gift shop, a tea house, and a museum. Initially, though, it was the nation’s first co-ed classroom.

But it’s fair to say that this isn’t the kind of classroom you’d have loved to join. The dungeon under the stairs alone will give you creeps!

Apparently, “unruly” students were sent in there for punishment. Regular time-out in the corner and detention in the library don’t sound too bad now, do they?

You can get a ticket to visit the Oldest Wooden Schoolhouse museum any day of the week.

However, if you want a well-rounded paranormal activity, you might want to sign up for a ghost tour of St. Augustine. The tour will take you to the schoolhouse and the Castillo de San Marcos National Monument.

Zipline Over Gators at St. Augustine’s Alligator Farm

Did you know the Sunshine State is home to more than a million alligators? Luckily, you don’t have to take a risk and stroll around freshwater lakes unsupervised to spot one.

The Alligator Farm on Anastasia Boulevard has all the gators you need, a whole lot of birds, and some lemurs to boot.

And if just looking at the gators isn’t enough to pump up your adrenaline, you can zip line through the treetops right above a bunch of gators and crocodiles!

I didn’t get a chance to zipline here myself, but I did zipline over gators in Louisiana, and I can confirm that it’s a thrilling experience. Why not go for it?

Marvel at the Miniatures in the Tiny Art Museum

For something really unique and fun, tour St. Augustine’s Tiny Art Museum, home to art pieces so small you can only see them through a microscope.

The exhibits are rotated regularly, and around 30 exhibits are displayed at any given time. The coolest pieces are the ones done in the eye of a needle. Really!

It doesn’t matter if it’s a scorpion, a violin, a key, or a bunch of camels in there. Just the fact that the pieces are displayed in the eye of the needle really puts things into perspective and makes the artwork even more impressive.

Sip From Ponce de Leon’s Fountain of Youth

fountain youth park

Ponce de Leon never did find that mythical Fountain of Youth. But today, visitors can explore the Fountain of Youth Archaeological Park, a site created as a tribute to the noted explorer.

This is the spot where de Leon allegedly landed in Florida in 1513. That claim is unsubstantiated, but the archaelogical park does contain remnants of an early Spanish settlement. 

The park also has exhibits and information about de Leon and the famous spring that he was searching for, which supposedly brought eternal youth to whomever drank from it.

Enter the Spring House to see the natural well that they actually call “the Fountain of Youth.” Grab a plastic cup and drink from the well yourself!

You’d better believe that I took a sip. Time will tell if it keeps me from aging.

fountain of youth st augustine

Oh. and there are lots of peacocks casually roaming around the property. Don’t be surprised if they walk right past you on the sidewalk.

Walk the Narrowest Street in the Country

Treasury Street is just over six feet wide, which makes it the narrowest street in the United States!

Interestingly, the street is narrow by design. Back in the day, the lane used to connect the waterfront to the Royal Spanish Treasury. So folks would frequently carry chests of gold back and forth from the ships along this street, leaving them vulnerable to attacks from thieves.

However, if the street is so narrow that it barely holds two men and a chest, then there’s no way a thief on a carriage could snatch the gold and make a run for it. Smart!

Today, there are no gold chests or horse carriages in sight. The road is a great place to take some selfies, as you can almost stretch your arms from one wall to the other.

Watch Surgical Demonstrations at the Spanish Military Hospital Museum

What was surgery like hundreds of years ago? Here’s your chance to find out.

A short walk from the Plaza de la Constitución is St. Augustine’s Spanish Military Hospital Museum, offering a chilling glimpse into the odd medical practices of the past. It’s similar to the Museum of Surgical Science in Chicago.

The daily tour includes a presentation on how colonial herbs were used to make many of today’s useful medicines. You’ll also see surgical demonstrations performed by physicians. 

The descriptions of amputations are rather graphic. And seeing all the rudimentary medical tools won’t help, either. So this might not be for the squeamish.

Witness Cannon Fire at Castillo de San Marcos

castillo de san marcos monument

The Spanish settlers built the fort that is now Castillo de San Marcos National Monument to defend their land in Florida and their shipping routes. It’s a fascinating historic attraction.

The quirky and unique part comes during the self-guided tour when you visit the soldiers’ sleeping quarters and see how they slept, cramped into a small room with several men in a row.

You can also see weapons demonstrations on weekends, when rangers fire muskets and cannons on top of the fort. How often do you get to see someone shooting off a cannon?

Start a Romantic Stroll From the Love Tree

Treasure Street isn’t the only place to take a quirky photo in St. Augustine. The Love Tree on Cordova Street is quite a strong contender, with a romantic vibe.

What’s so special about it? For starters, it’s not one tree. Somehow, a palm tree ended up growing on a gnarled oak tree. 

Now, the two share a spot, one growing on top of the other. Florida’s damp weather likely played a role here because this isn’t the only Love Tree in St. Augustine.

Local legend has it that one person planted the oak. Another planted the palm in the crevice on the oak, and the two fell in love. The fusing trees symbolize their relationship.

What’s a better place to start a romantic stroll? There’s even a gift shop on the property that owns the tree, so you can buy a souvenir before you take a walk and look for the other less famous (but still just as magical) love trees in the area.

Creep Yourself Out at the Medieval Torture Museum

The stuff inside the Medieval Torture Museum on St. George Street is pure nightmare fuel. But some folks will find it worth checking out every horrific prop in the candle-lit chambers.

To take the experience to the next level, the exhibitions don’t just show you the (reconstructed) torture equipment. Instead, the whole scene is set up with realistic silicone figurines, fake blood, audio guides, and interactive opportunities.

“Our main product is emotion” is the museum’s tagline. When you visit, you’ll get the chance to view the display both as the cruel tormentor and the suffering tormented.

Try Unique Whiskeys at City Gate Spirits

city gate spirits

Looking to try some unusual adult beverages? Head to City Gate Spirits, a distillery on St. George Street that makes very unique flavors of rum, vodka, and other liquors.

Among their fascinating varieties are Grapefruit Vodka, Peanut Butter Whiskey, Orange ‘n Cream Moonshine, and Smoked Maple Whiskey. Take home a bottle or two if you’re so inclined.

The best part is they have a tasting room where you can sample some of the goods. I tried several flavors and can personally vouch for the deliciousness of the Sweet Tea Vodka and Apple Pie Moonshine.

Check out Churchill’s Lion at the Lightner Museum

British Prime Minister Winston Churchill once owned a lion named Rota. Today, the stuffed body of that lion can be found inside the Lightner Museum in St. Augustine, just across the street from Flagler College.

Why is it here? Who knows?! It’s not clear how the lion made its way to Florida, but visitors can see the mammoth feline inside a glass case in the museum.

While Rota is the highlight of the facility, the quirky toaster collection on the second floor is also worth checking out.

When you’re done touring the museum, grab a drink in the cafe. The space used to be the largest indoor swimming pool in the US at one point!

See the Sacred Cat Rug at the Villa Zorayda Museum

The Villa Zorayda Museum is “a historic guilded age museum.” Inspired by Spain’s Alhambra Place, the house was built in 1883 and offers tours in English and Spanish.

The two relics worth seeking out are the Sacred Cat Rug and the mummified foot in the Egyptian exhibit. The mummified foot was found years ago wrapped in the rug. 

It was later discovered that the rug, which depicts a large cat, is more than 2400 years old, making it one of the oldest surviving rugs on the planet. 

These two relics alone make Villa Zorayda worth visiting, but you’ll also enjoy the mini-Moorish design and the fine art.

Spend a Confusing Afternoon at Ripley’s Believe It or Not

There’s nothing like a good Ripley’s Believe it or Not museum. They can be found all over the world, from San Antonio to Amsterdam to Pigeon Forge, Tennessee

Luckily, St. Augustine has its own Ripley’s Believe It or Not on San Marco Avenue, and this location is chock-full of oddities.

We’re talking matchstick replicas of the International Space Station, Chewbacca fur, genuine shrunken heads (yes, quite controversial!), and a vortex tunnel.

You might even catch a hands-on haunted castle investigation. The experience is designed to be as “realistic” as possible with thermal imaging cameras and EVP recorders.

Relive the Titanic Voyage at the Shipwreck Museum

shipwreck museum

From the Titanic to the Edmund Fitzgerald, shipwrecks hold a fascinating place in history. The Shipwreck Museum and Gallery on Charlotte St. is the place to learn about them.

Items on display here include props from the Titanic movie and artifacts from passenger ships that sank, some of which are hundreds of years old.

Basic admission is $15, though you can pay extra for guided tours or a special treasure hunt.

Hunt for Treasure at the Pirate Museum

If you have kids, be sure to visit the Pirate and Treasure Museum on South Castillo Drive. It has some thematic overlap with the Shipwreck Museum, but this one focuses more specifically on pirates.

This museum aims to transport visitors back 300 years in time, when piracy was a major problem on the world’s seas and oceans.

Adults and older kids will enjoy the authentic artifacts. The little ones, on the other hand, will love looking for the hidden boxes in the displays.

Spend the Night in a Shipping Container House

There are lots of hotels and short-term rentals in St. Augustine. But how many of them are made with shipping containers and feature kooky murals?

Yes, you can stay in a house literally constructed from semi-truck containers. The Prince Road Container House features Andy Warhol-style art and several rooms built from nine shipping containers. It’s only a short drive from the Lightner Museum.

Spending a night here will set you back quite a bit of money — the average daily price is $515 and there’s a minimum two-night stay — but it’s undoubtedly one of the most unique things to do in St. Augustine.

Other Unique Things To Do in St. Augustine

old town trolley tours

If this list isn’t comprehensive enough, here are a few more spots you may want to consider adding to your itinerary in the nation’s oldest city, covering historic forts, wildlife adventures, and other historic structures.

Potter’s Wax Museum: The oldest wax museum in the country, Potter’s came way before Madame Tussaud. This one has replicas of historic figures like Martin Luther King and Ben Franklin, plus celebrities like Michael Jordan and George Costanza from Seinfeld.

Old Town Trolley Tours: Get around Downtown St. Augustine in style with the Old Town Trolley Tour. The basic tour makes 22 stops and runs all day. They also offer special evening ghost tours. Book the ghost tour here.

Kayak or Paddle with Manatees and Dolphins: Jump in a kayak and paddle along some of the historic city’s waterways with a guide. If you’re lucky, you may spot dolphins, manatees, turtles, or rays. Book the experience here.

Oldest Store Museum Experience: This place aims to take visitors back to the year 1900. Live actors play the roles of clerks and butchers as they show you what stored were like a century ago.

Marineland Dolphin Adventure: Swim with dolphins at Marineland, an aquatic playground located 30 minutes south of Downtown St. Augustine on Oceanshore Blvd by the Atlantic Ocean.

Bridge of Lions: Drive across this imposing bridge, or just walk up to the two large lion sculptures on either side.

St. Augustine Lighthouse and Maritime Museum: Learn about 500 years of maritime history here and see the 150-year-old lighthouse at one of Saint Augustine’s best places for local history.

Flagler College: Visit Flagler Fountain to see a replica of Ponce de Leon’s sword at the center of the fountain. The campus is listed on the National Register of Historic Places, because it used to be the Hotel Ponce de Leon.

Fort Matanzas National Monument: Visit a 1740 Spanish coastline fort surrounded by 100 acres of salt marsh. Guests must take a 5-minute ferry from the visitor center across to Fort Matanzas itself.

I visited St. Augustine as part of an Orlando to Savannah road trip. If you’re heading down to Orlando, check out our list of non-touristy things to do there.

Do you have any other suggestions for unique things to do in St. Augustine, Florida?

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