Our plans for a Saturday of exploring downtown over our long weekend in 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.
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.
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.
First stop: the Castillo de San Marcos fort.
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.
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.
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.
I’ve said it before and I’ll say it again: You can’t beat Florida sunsets.
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.
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.
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.
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.
Isn’t this just the prettiest spot for a family portrait?
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 eat list during your weekend in St. Augustine.
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.
That’s a wrap, Florida—what a perfect weekend in St. Augustine it was indeed.
Looking for other trip ideas to Florida? I’ve got a few:
- Swimming with Manatees in Crystal River
- 4 Ways to Explore Jacksonville
- Taking Your Dog to South Walton
- Planning the Ultimate Vacation in the Florida Keys
- Getting Your Water Park on at Volcano Bay
- Planning a Gulf Coast Bachelorette
- Experiencing the Magic at Wizarding World of Harry Potter
- Going Wreck Diving in the Gulf of Mexico
- Swimming with Dolphins in PCB