10 Cool and Unique Things to Do in St. Augustine

unique things to do in St. Augustine - Aviles Street at night.

St. Augustine is the oldest city in the United States, but don’t mistake that title for being antiquated and outdated. The city is a cultural mecca by day, and a vibrant wonder by night. So, what are the best things to do when you visit? From eco water tours to tasty treats, here are 10 cool and unique things to do in St. Augustine.

unique things to do in St. Augustine - Magnolia Boulevard
The lovely Magnolia Boulevard in St. Augustine. Photo Credit: Karyn Locke
    1. Walk Down the Oldest Street in the U.S.
    2. Visit a Spanish Fort
    3. Stay at the Oldest Inn in America
    4. Taste Test an Ice Cream Sandwich with a Cool History
    5. Take a Three-Hour Drinking Tour of Downtown
    6. Drink at the First Distillery Opened in Florida Since Prohibition
    7. Head Out on the Water for a Dolphin Eco Tour
    8. Dine in a Swimming Pool
    9. Watch a Classic Movie in all the Comforts of Home
    10. Check Out A College that Was Once a Hotel for the Rich

Disclosure: I was graciously hosted by Leigh Cort Publicity and the folks at The St. Francis Inn. All opinions are my own!

As a gal bitten by the travel bug, when I find a cool city, I’m always happy to share my take and what to do when visiting. For St. Augustine, FL, narrowing down a top 10 list was pretty difficult, but I managed to do it. I spent plenty of time on the Old Town Trolley Tours (it allows you to hop on and off at 23 popular locations around the city), and fell in love with everything the city has to offer both its residents and guests. 

It’s a city that’s been on my travel bucket list for at least 10 years ( I really learned about how cool it was when visiting St. Simons Island, GA, believe it or not), and I’m happy to say it’s officially been ticked off my list. Here are my favorite things to do when you visit. 

1. Walk Down the Oldest Street in the U.S.

unique things to do in St. Augustine - Aviles Street
The oldest street in America – Aviles Street. Photo Credit: Karyn Locke

I love, love, love American history. Put me smack dab in the middle of it and I’m a happy camper. Let me walk down the oldest street in the United States and I’m not only walking, I’m doing the happy dance. 

Aviles Street has been a name on the maps since around 1570. Let’s think about that for a second. In 50 years it will be 500 years old! What’s super cool about Aviles is he fact that it’s pedestrian traffic only, so feel free to mosey and take photos, especially at night when it’s lit up. 

2. Take a Tour of the Oldest Masonry Fort in the United States

unique things to do in St. Augustine - Castillo de San Marcos
Castillo de San Marcos in St. Augustine. Photo Credit: Karyn Locke

Again with the American history happy dance, but Castillo de San Marcos is definitely worthy of mention. Celebrating its 315th birthday, the Castillo is a beautiful piece of architecture. If you look at photos from above, it kind of reminds me of a Chinese throwing star. 

Tours are given daily with admission ($15 per person aged 16 years and older) and are good for 7 consecutive days. But, if I’m being honest, at sunset (after the 5pm closing) is when it looks the most beautiful. Folks gather around the fort and its exterior for a gorgeous view of the water. 

3. Unique Things to Do in St. Augustine: Stay at the Oldest Inn in America

unique things to do in St. Augustine - St. Francis Inn Wilson Suite
The Wilson Suite Master Bedroom in St. Francis Inn. Photo Credit: Karyn Locke

During my visit, I had the absolute pleasure of staying at The St. Francis Inn. Dubbed the oldest inn in the U.S., it has several lodging styles and buildings. There’s everything from cozy rooms to suites filled with old-fashioned touches. 

During the visit, The Kid and I stayed in The Wilson Suite. Located across from the main Inn in The Wilson House, we had plenty of room to get out of each other’s way (she is 17, after all).

I had a super comfy king bed and she took the living area with a pull out sofa. Each suite in The Wilson house has its own outdoor space, and our upstairs porch (complete with porch swing!) was perfect for sipping Peach Tea. 

unique things to do in St. Augustine - St. Francis Inn outdoor patio
The outdoor patio at St. Francis Inn is magical, especially at night. Photo Credit: Karyn Locke

As for amenities, they’re plentiful. We had free parking, complimentary snacks and drinks, an outdoor pool, and a full breakfast each morning. At night, if you have a sweet tooth, you’ll get a homemade dessert to enjoy in the common space or in your room, too. 

The innkeepers, Margaret and Joe Finnegan, are personable and warm. If you visit, get to know them. You’ll end up with two new friends. 

4. Unique Things to Do in St. Augustine: Taste Test an Ice Cream Sandwich with a Cool History

unique things to do in St. Augustine - Peace Pie
Peace Pie ice cream sandwiches on Avila Street. Photo Credit: Karyn Locke

If you know me, you know that ice cream is my favorite food. So a chance to test drive a delicious ice cream sandwich with a cute backstory? I’m down. You know the phrase, “Necessity is the mother of invention”? That’s Peace Pie.

The brainchild of Jerry Clause, the idea came from forgetting to bake pie shells one Thanksgiving. So, with two massive shortbread cookies, pecan pie filling, and ice cream, he put them all together and, Voila!, Peace Pie was born the next year. 

These days, each Peace Pie has a layer of pie filling inside and the flavors are not only creative, they’re delicious. Located on Avila Street, definitely try the Pecan Pie version if you don’t have a nut allergy. 

Headed to St. Augustine, FL, and on the hunt for the coolest things to do when you visit? From on-the-water eco tours to walking the oldest street in America, here are 10 cool and unique things to do in St. Augustine! #VisitStAugustine #LoveFL #VisitFL #StAugustine #Travel #FamilyTravel #CouplesTravel

5. Take a Three-Hour Drinking Tour of Downtown

unique things to do in St. Augustine - The Tasting Tours
What a way to kick off a food and drink tour with The Tasting Tours – Prosecco! Photo Credit: Karyn Locke

Hey, when there’s a three-hour drinking tour of a gorgeous city, complete with a witty tour guide, I’m down. 

The Tasting Tours is an ideal way to see the city and get a feel of its liquor-infused hot spots. With Corlee as our tour guide, he whisked me and six other ladies around the old streets of St. Augustine to five stops filled with light bites and drinks. 

unique things to do in St. Augustine - The Tasting Tours dessert
A sweet ending to an even sweeter tour with The Tasting Tours. Photo Credit: Karyn Locke

The tasting tours are super popular, so if you know you’ll want to take one, head to the official website to check out the options. 

6. Drink at the First Craft Distillery Opened in Florida Since Prohibition

unique things to do in St. Augustine - S. Augustine Distillery.
Trying a Tropical Tiki drink at St. Augustine distillery. Photo Credit: Karyn Locke

Repurposing an old ice plant and turn it into a hard liquor distillery? That’s was the dream for the folks at St. Augustine Distillery. Not only does it whiskey, rum, vodka, and gin, it makes fine examples of all. 

I had a chance to taste test its spirits on a press tour, including its own recipes for cocktail mixes, and found them simply delightful. Prices are higher than what you’d find in a state store, but that’s to be expected as the batches are much smaller. 

7. Unique Things to Do in St. Augustine: Head Out on the Water for a Dolphin Eco Tour

unique things to do in St. Augustine - St. Augustine Eco Tours
A look at the Castillo de San Marco from the water with St. Augustine Eco Tours. Photo Credit: Karyn Locke

When you look at the gorgeous water around St. Augustine, have you ever stopped to think about the ecology of it? Truthfully, I was pretty guilty for not doing so. But, a morning out on the water with St. Augustine Eco Tours definitely changed my thinking. 

Zach McKenna, our guide for the tour, gave amazing insight to the ocean ecology and how we affect it everyday. He’s so passionate about it, in fact, that we made pit stops to pick up plastic and cans floating in the water.

We also tried to see a few dolphins on our tour, but no luck. And you know what? I’m not mad about it. That means the dolphins in the area haven’t been coerced to come over to boats, potentially injuring them. 

8.Unique Things to Do in St. Augustine: Dine in a Swimming Pool

unique things to do in St. Augustine - Cafe Alcazar
Cafe Alcazar interior. Photo Credit: Karyn Locke

Once upon a time in 1888, a man named Henry Flagler (VERY well known in St. Augustine), made the Alcazar Hotel. and in that hotel sat a massive swimming pool. The world’s largest swimming pool, in fact. It was a spot for the affluent, and henry Flagler sure loved folks with money to spend in his properties. 

unique things to do in St. Augustine - Cafe Alcazar charcuterie
Creative charcuterie at Cafe Alcazar. Photo Credit: Karyn Locke

Fast forward to today where the property is now home to the Lightener Museum. Where the pool used to be is now the space of Café Alcazar, an upscale restaurant. You’ll find unique dished made with local, organic ingredients and beautiful ambiance. 

I’m sure Mr. Flagler would approve. 

9. Unique Things to Do in St. Augustine: Watch a Classic Movie in all the Comforts of Home

unique things to do in St. Augustine - Corazon Cinema
Comfy seats and a cool vibe at Corazon Cinema and Cafe. Photo Credit: Karyn Locke

Think about how you like to watch movies at home for a sec. Personally, I like a good, comfy chair, delicious popcorn, and a nice drink to sip on. That’s Corazon Cinema and Café in a nutshell.

Owner Karla Wagner seems to have the same idea and has decorated all three of her theaters to reflect a homey, comfy feel. You’ll find leather chairs right along with the first run and independent films she offers. 

10. Take a Tour of the First Building in America to offer Electricity

unique things to do in St. Augustine - Flagler College tour
The beautiful exterior of what was once the Ponce de Leon Hotel – now Flagler College. Photo Credit: Karyn Locke

Ahh, Henry Flagler. The man loved building swanky hotels for rich people. But, these days, his properties have been repurposed, as they should. Here’s a quick backstory.

In 1885, Mr. Flagler decided to build the massive Ponce de León Hotel. In 1888, it was officially completed. Yeah, three years to build a massive, and I mean massive, property. It was the winter home for many rich folks and they were doted on extravagantly. It was also the first building to offer DC current from its beginnings, aka electricity, compliments of Flagler’s friend, Thomas Edison. Yeah. 

unique things to do in St. Augustine - Flagler College Tiffany Ceilings
That famous Tiffany Blue in the ceilings of Flagler College. Photo Credit: Karyn Locke

Nowadays, the hotel is home to Flagler College. It offers its students a chance to dine surrounded by Tiffany Windows, along with a top-notch education. 

If you’re anywhere near Flagler College, check the tour times. I was astounded by Flagler’s attention to detail and love of beauty and the tour really drives it home. 

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One Thought to “10 Cool and Unique Things to Do in St. Augustine”

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