Florida Travel: Exploring the Old City of St. Augustine

Adventures with Family in St. Augustine

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Jade and I became online friends over seven years ago through secret Tumblrs we both maintained. We’ve been IRL friends for more than five, having traveled all over together: California, Florida, Kentucky, Tennessee, the Caribbean and beyond. Let me just tell you how awesome it is to go from thinking you like someone a whole lot via their online persona to discovering you straight-up adore them in real life.

Florida Travel: Exploring the Old City of St. Augustine

That’s not always the case. Luckily, with Jade, it was.

In fact, we were in Tahoe this very week last year with her husband Bob and our friend Spencer when she told me in private: “I think I might be pregnant.”

“Nah,” I brushed it off. Drink some more bourbon; that’ll help ease your worries.”

Eight months to the day later, Augustine was born. I’m clearly a great role model. (Pregnant women, call me!)

Florida Travel: Exploring the Old City of St. Augustine

And ever since her debut in November, I’ve been trying to find a time to meet Mini Jade. First, I was going to fly to LA to do just that, then was told they’d be in Florida for a week in early March. And you know me, any chance to escape to Florida, I’m in!

Florida Travel: Exploring the Old City of St. Augustine

The last time I saw Jade and Bob in September, they were a family of two (plus two fur kids); now, they’re a party of three. It’s a pretty cool thing to see such a transition take place, especially when your best friend is killing it with the whole mom thing (Bob, you aren’t doing shabby either!). Also, let’s just talk about how perfect this baby is, too:

Florida Travel: Exploring the Old City of St. Augustine

It only made sense that I’d meet Augustine in the city that lent her its name. Jade grew up in Jacksonville, and her parents moved further south to St. Augustine around the time we graduated high school. She and Bob married there a few years back, and it’s apt that their littlest love would be named after their greatest love (prior to her, of course).

Florida Travel: Exploring the Old City of St. Augustine

And not five minutes after meeting them in downtown St. Augustine, I fully understood why they are so intoxicated by this coastal town.

Fun fact: Not only is St. Augustine Florida’s oldest city, it’s also the oldest city in the nation!

Florida Travel: Exploring the Old City of St. Augustine

After making the 45-minute drive from Jacksonville—so easy! so quick! so little traffic!—I met Jade, her mom Micki, Bob and Augustine at Mojo BBQ Old City, where they were having lunch. From there, we set out on foot and canvased the downtown over the course of the next four hours. I love how they didn’t think twice about putting Augustine in her stroller and carting her all over; I knew Jade and Bob would be the type of parents (i.e. my favorite kind) whose child would adapt to their lifestyle and not vice verse.

Florida Travel: Exploring the Old City of St. Augustine

Our self-guided tour began with a stroll around the Flagler College. I had a few friends who went to college here, and I was immediately jealous that they got to spend four (or in many cases, maybe five) years on such a gorgeous campus.

Florida Travel: Exploring the Old City of St. Augustine

I took a peek around to find marvelous architecture hiding behind every corner.

Florida Travel: Exploring the Old City of St. Augustine

Flagler alums, how do you get anything done here? Inevitably, I’d spend all day every day wandering around and taking photos instead of going to class.
Florida Travel: Exploring the Old City of St. Augustine

Florida Travel: Exploring the Old City of St. Augustine

Then we set off across the way to the Plaza De La Constitucion (or simply, “the Plaza”). We also popped into the iconic Casa Monica Hotel just to gawk over the gorgeous furnishings. We were staying with her amazing parents in their fabulous beach house, but I’m thinking next time I head down for a visit, Jade, Augustine, Micki and I need a girlfriend getaway at this awesome property.

Florida Travel: Exploring the Old City of St. Augustine

From there, it was onto St. George Street, the epicenter of St. Augustine’s tourist activity with plenty of equally beautiful buildings to boot.

Florida Travel: Exploring the Old City of St. Augustine

Florida Travel: Exploring the Old City of St. Augustine
Florida Travel: Exploring the Old City of St. Augustine

One of the Enterprise employees at the airport had gone to Flagler and advised me, “you simply can’t go to St. Augustine without getting a Popsicle at the Hyppo.” And who am I to argue with a local? You always take the local’s advice, y’all (unless that’s to eat at Bubba Gump’s and drink at Hard Rock Cafe, that is…ha).

Hyppo Pops: Exploring the Old City of St. Augustine

Very high on our agenda was a visit to St. Augustine Distillery. You guys know me and my love for all things booze—so many friends, both Floridians and otherwise, had told me what a killer spot this was, so we just had to go.

Florida Travel: Exploring the Old City of St. Augustine

It lived up to the hype, pals.

The local distillery opened in a National Register of Historic Places building in 2014 and focuses on a number of small batches—whiskey, vodka, rum and gin—made from Florida-farmed sugar cane and botanicals and regional molasses. It’s rare you find such a spirits company that does a little of everything, and St. Augustine Distillery reminded me of one of my favorite Nashville spots, Corsair, for that very reason.

St. Augustine Distillery: Exploring the Culinary Side of Florida

Florida Travel: Exploring the Old City of St. Augustine
Florida Travel: Exploring the Old City of St. Augustine

St. Augustine Distillery: Exploring the Culinary Side of Florida

Full disclosure, we opted not to actually do the distillery tour because a) we had a baby with us (though none of us had qualms taking her through the space, it was an hour-long commitment) and b) it was 5pm and happy hour time!

Instead, we checked out the shop, did some tastings, then went upstairs for a proper cocktail at the Ice Plant Bar.

This was a brilliant plan on our part if I do say so myself.

Florida Travel: Exploring the Old City of St. Augustine
Florida Travel: Exploring the Old City of St. Augustine

Florida Travel: Exploring the Old City of St. Augustine

St. Augustine Distillery
Put what you want
Put what you want

While the bar is on the second floor of the distillery, it’s not actually the same company. Rather, it’s a speakeasy-style cocktail concept with a keen focus on—you guessed it—ice that occupies a 1927 ice plant. Jade and I opted for Florida Mules made from the distillery’s own vodka. The space was gorgeous, and I could have easily wiled away the evening cozied up to the bar here. But we had places to be and people to see.

After cocktails, it was time to pack up and head over the bridge to Vilano Beach for the night. My trip was just getting started.

Sunset at Vilano Beach

Florida Travel: Exploring the Old City of St. Augustine
Florida Travel: Exploring the Old City of St. Augustine

Florida Travel: Exploring the Old City of St. Augustine

Looking for other trip ideas to Florida? I’ve got a few:

Florida Travel: Exploring the Old City of St. Augustine
Florida Travel: Exploring the Old City of St. Augustine
COMMENTS
  • March 14, 2016

    Ummmmm, put St. Augustine on the must visit list, pronto! How gorgeous! And that kid … ahhhhdorable 🙂 Oh, and PS – your images are always fantastic, but there’s just something about these that are especially killer!

    • March 14, 2016

      You’re the sweetest! I still get a little frustrated that my WP site seems to compress them a bit, but I appreciate you saying that—makes me feel better about the quality 😉

    • March 14, 2016

      Totally agree about the images here- they look soo good! (And I’m not saying that cause I’m in them!)

  • March 14, 2016

    Palm trees and no miles and miles of desert, suburban sprawl are so dreamy!! (Grass is always greener, right? Although, to be fair, at least in St. Augustine they actually HAVE grass….)

    xox

  • March 14, 2016

    Wow, totally not what you’d expect in Florida. As long as I can make it to Cape Canaveral within reason, I’d be interested in checking this place out.

    • March 14, 2016

      You bet! Just two hours by car. My parents have had a timeshare in Orlando since I was a wee kid, and we did a day trip to the Cape nearly every summer!

  • March 15, 2016

    Omg the pictures are incredible and the baby so cute

  • March 15, 2016

    Please come to Denver (or anywhere in the mountains) and follow me around with a camera. K thanks 🙂

  • March 15, 2016

    SO glad you went to Ice Plant. Hands down my favorite bar in the Jax area! They house make their own cola for whiskey and coke and it’s divine.

  • March 15, 2016

    What an incredibly cute couple and baby! 🙂

    Either my perception of Florida is completely off, or St. Augustine does not look like a town in Florida; in a good way though! There’s so much in the US I have yet to explore! Your posts are a constant reminder how much I’m missing on the other side of the pond 😉

  • March 15, 2016

    Gorgeous shots, especially of baby A!!!

  • March 17, 2016

    Kristin,
    Truly stunning pictures out here.
    and yeah as everybody talking out there regarding the baby, he is really so cuteeee 😉

  • March 19, 2016

    I made a day trip of St. Augustine once (waaay back… in 2007) but I feel like I missed out on so many cool sights downtown. Way to capture them!

  • March 11, 2017

    First of all, I love reading this page. My wife and I visit St. Augustine every year and it is our favorite place to vacation. I finally decided to build a website to highlight some of our adventures there. So many attractions, great restaurants and beautiful beaches! I hope you enjoy…
    http://staugustineadventure.com

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