Exploring St. Augustine: Welcome to Florida's—not the mention, the country's—oldest city.

Visit Florida: Scenes from St. Augustine’s Old City

Our plans for a Saturday of exploring downtown St. Augustine were thwarted by some ridiculous traffic thanks to an annual seafood festival that seemed to bring every Florida resident from far and wide to the small coastal city. Instead of braving that particular avenue of chaos, we spent much of the day in the car going to/from a birthday party on Anastasia Island instead then scrapped the idea of heading into town for drinks before our evening concert entirely.

Exploring St. Augustine: Welcome to Florida's—not the mention, the country's—oldest city.

As a teen, I was a frequent visitor to Nashville’s own amphitheater, Starwood, but it shuttered shortly after I graduated college and I missed balmy nights spent out on the lawn watching Dave Matthews Band and Counting Crows each summer when they’d swing through the South on tour (does that date me or what?). Nashville did get a fancy new amphitheater right on the waterfront and I’ve loved the couple shows I’ve attended there, so when Jade asked if I’d be game for a Jason Isbell and Shovels & Rope concert, there was only one answer: DUH.

St. Augustine Amphitheatre is a 3,493-seat outdoor venue on Anastasia Island, and it’s a spectacular spot for a nighttime show. While we had purchased seats, the ticket checker at the gate new Jade from when she was a wee thing, and handed us all pit tickets. Score! If there’s anything better than seeing Jason Isbell in a bad-ass venue in Florida on a perfect spring night it’s seeing Jason Isbell from the pit of a bad-ass venue in Florida on a perfect spring night.

Jason Isbell at the St. Augustine Amphitheatre

We stayed out past our bedtime that night and crawled into bed well after 2am, so Sunday morning was a bit of a lazy start. After our epic beach morning with the clan, Jade’s brother and his posse headed back home to Gainesville while Jade, Bob and I left Augustine at home with the grandparents and headed into her namesake town kid-free.

Exploring St. Augustine: Welcome to Florida's—not the mention, the country's—oldest city.

First stop: the Castillo de San Marcos fort.

Exploring St. Augustine: Welcome to Florida's—not the mention, the country's—oldest city.

Exploring St. Augustine: Welcome to Florida's oldest city.
Exploring St. Augustine: Welcome to Florida's oldest city.

Exploring St. Augustine: Welcome to Florida's—not the mention, the country's—oldest city.

Exploring St. Augustine: Welcome to Florida's oldest city.
Exploring St. Augustine: Welcome to Florida's oldest city.

This national monument was one of the first walled cities in America, and we arrived as the sun was setting, snagging free street parking right near the fort’s entrance. We strolled the fort’s circumference, monkeying around on the stone ledge, our shutters clicking in tandem.

Exploring St. Augustine: Welcome to Florida's oldest city.

Then we looped back to nearby St. George Street for one reason—chocolate-covered key lime pie on a stick—marveling at the number of outdoor cafes the Old City boasts and wishing we weren’t flying back to our respective parts of the country the following morning so we had time to try them all.

Exploring St. Augustine: Welcome to Florida's oldest city.

Exploring St. Augustine: Welcome to Florida's oldest city.
Exploring St. Augustine: Welcome to Florida's oldest city.
Exploring St. Augustine: Welcome to Florida's oldest city.

Exploring St. Augustine: Welcome to Florida's—not the mention, the country's—oldest city.

Exploring St. Augustine
Exploring St. Augustine

As we circled back to our rental car—a minivan as seemed fitting for Jade and Bob’s first family trip as parents—the coastline glowed softly in a rainbow of pastels.

Exploring St. Augustine: Welcome to Florida's—not the mention, the country's—oldest city.

Exploring St. Augustine: Welcome to Florida's oldest city.
Exploring St. Augustine: Welcome to Florida's oldest city.

Exploring St. Augustine: Welcome to Florida's—not the mention, the country's—oldest city.

I’ve said it before and I’ll say it again: You can’t beat Florida sunsets.

Exploring St. Augustine: Welcome to Florida's—not the mention, the country's—oldest city.

It was such a beautiful night, if not a bit chilly, and we started to head home but couldn’t pass up the chance for one last sunset vantage point. So we made one last stop and posted up at the outdoor bar at Beaches at Vilano for a pre-dinner beer.

Exploring St. Augustine: Welcome to Florida's—not the mention, the country's—oldest city.

There are a number of beach shacks and restaurants in Vilano and we had planned to eat out at one on our final night in town, but in the end, we were all wiped from the night before and our afternoon of playing tourists and all had to catch up on work (read: adulting), so instead we headed back to Jade’s parents’ house for an evening in.

Exploring St. Augustine: Welcome to Florida's—not the mention, the country's—oldest city.

The next morning we had a very special stop to make before our flights: We swung by Ponce de Leon’s Fountain of Youth, where Bob and Jade got married in 2013, to take a couple photos of the new family of three beneath the beloved tree where they exchanged vows.

Exploring St. Augustine: Welcome to Florida's oldest city.

Exploring St. Augustine: Welcome to Florida's oldest city.
Exploring St. Augustine: Welcome to Florida's oldest city.

Exploring St. Augustine: Welcome to Florida's oldest city.

While we didn’t have time to explore the grounds themselves—other than to sneak a quick peek at the free-roaming peacocks—we did pause for a moment to admire Magnolia Avenue, one of the most photographed cities in the country which also happens to lead right to the entrance of the Fountain of Youth.

Exploring St. Augustine: Welcome to Florida's oldest city.

Exploring St. Augustine: Welcome to Florida's oldest city.
Exploring St. Augustine: Welcome to Florida's oldest city.

Isn’t this just the prettiest spot for a family portrait?

Exploring St. Augustine: Welcome to Florida's oldest city.

We also did get to see the beach part of Anastasia Island right before I headed out of town to catch my flight from Jacksonville. I love the ease of flying into the Atlantic Coast and how it took no time to make it from lunch at Mango Mango’s, one of Jade’s favorite local haunts. After a feast of coconut shrimp and pulled pork corn cakes, let me just say this: Mango Mango’s needs to be on your St. Augustine eat list.

Exploring St. Augustine: Welcome to Florida's—not the mention, the country's—oldest city.

Since we were just feet from the beach, obviously we had to stop for a brief photo shoot. It would have been criminal not to. Though they’re but miles apart. Anastasia Island’s dunes are so dramatically different than the beaches of Vilano.

Exploring St. Augustine: Welcome to Florida's—not the mention, the country's—oldest city.

Exploring St. Augustine: Welcome to Florida's oldest city.
Exploring St. Augustine: Welcome to Florida's oldest city.

Exploring St. Augustine: Welcome to Florida's—not the mention, the country's—oldest city.

Exploring St. Augustine: Welcome to Florida's oldest city.
Exploring St. Augustine: Welcome to Florida's oldest city.

Exploring St. Augustine: Welcome to Florida's—not the mention, the country's—oldest city.

That’s a wrap, Florida—glad I’ll be back in your loving embrace in just three weeks’ time!

Exploring St. Augustine: Welcome to Florida's—not the mention, the country's—oldest city.

Florida Travel: Exploring the Old City of St. Augustine
Florida Travel: Exploring the Old City of St. Augustine
COMMENTS
  • March 21, 2016

    Beyond gorgeous every picture!
    Andi recently posted..Celebrating International Day Of Happiness For The First TimeMy Profile

    • March 22, 2016

      I can’t wait till you take baby J there!

  • March 21, 2016
    Micki Broadus

    Beautiful pictures. Happy I was a part of this fun weekend. My new Tennessee daughter.

    • March 22, 2016

      Now you owe me a Nashville trip so I can spoil you and Matt on my home turf! =)

  • March 21, 2016

    You lost me for a second there when you said you skipped the Seafood Festival. How could one skip any kind of food festival, I asked myself, until I read about the chocolate covered key lime pie on a stick and the delicious food you had at Mango Mango. The world makes sense again 🙂
    Dominique recently posted..Bonaire – Kralendijk and RinconMy Profile

    • March 22, 2016

      If you had seen the traffic, you would have, too! It was INSANE. Took us an hour just to go about five miles.

      But that Mango Mango’s meal more than made up for it!

    • March 22, 2016

      Yes, Dominique! I would never deprive Kristin of good seafood- but wanted something a little less touristy, plus I realized she had never had fried shrimp before (!!!) so we had to remedy that asap. 🙂
      Jade recently posted..#KidAugustine’s first Sunset Beach Day & Fire Pit PartyMy Profile

      • March 24, 2016

        What is this fried shrimp of which you speak?

  • March 22, 2016

    Your pictures are incredible! Was there stained glass in the background of the venue for the Jason Isabell show? Looked beautiful

    • March 22, 2016

      Thank you, Alexa! Yes, the stained glass was part of his set design (I think). I imagine it was meant to look like the Ryman!

  • March 22, 2016

    Beautiful photos!
    Linda recently posted..Today’s SmilesMy Profile

  • March 22, 2016

    OMG, that photo of Magnolia Avenue – and that beach! This is definitely a part of Florida I still need to explore!
    Amanda recently posted..How Blogging Has Changed the Way I TravelMy Profile

    • March 24, 2016

      And I need to go to the springs! We can flip-flop and give each other tips (I’ve had your Crystal Springs post bookmarked ever since you wrote it!).

  • March 27, 2016

    I definitely think that Florida has the prettiest water, and that’s with me visiting the Polynesian Islands several times. I have not been to Greece (the closest I got was Cyprus) so until I can get there and see for myself, I think Florida will reign in this area.
    Andi recently posted..Weekly Wanderings #10 – Bryce CanyonMy Profile

    • March 27, 2016

      I agree with you there! Cannot WAIT for you to experience the Panhandle (have you been before? can’t remember). I’m actually headed there with Jade in two weeks =)

  • April 19, 2016

    I’ve never heard of St Augustine. Seems like a nice mix of history and culture. Lovely photos.
    Liam recently posted..The Aussies’ Favorite Places To VisitMy Profile

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