St. Augustine is the oldest city in the United States, but don’t mistake that title for being antiquated and outdated.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. I’ve partnered with Hotels.com to share some of 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.
- Walk Down the Oldest Street in the U.S.
- Visit a Spanish Fort
- Stay at the Oldest Inn in America
- Taste Test an Ice Cream Sandwich with a Cool History
- Take a Three-Hour Drinking Tour of Downtown
- Drink at the First Distillery Opened in Florida Since Prohibition
- Head Out on the Water for a Dolphin Eco Tour
- Dine in a Swimming Pool
- Watch a Classic Movie in all the Comforts of Home
- Check Out A College that Was Once a Hotel for the Rich
Disclosure: I was graciously hosted by 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. Narrowing down a top 10 list of things to do in St. Augustine, FL, 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.
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 the 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
Again with the American history happy dance, but Castillo de San Marcos is definitely worthy of mention. Celebrating its 315th birthday, 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
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.
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
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.
5. Take a Three-Hour Drinking Tour of Downtown
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.
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
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
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
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.
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
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
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.
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.