A Long Florida Weekend: Jacksonville & St. Augustine

I was recently in Florida for a wedding, and while I’ve been to multiple cities in Florida, this visit allowed me to experience two places I’d never been – Jacksonville and St. Augustine.


Jacksonville wasn’t really an intentional stop, more of just a place to crash after arriving at the Jacksonville airport. Other than enjoying the Hyatt I was able to stay in for free (gotta love rewards points) and some nice walking paths, there wasn’t a lot to do near the hotel. A positive about this hotel is that there are two restaurants and a bustling bar on site so you don’t necessarily need to leave the property to have a good time! And I can vouch for the food being great there.

A short Uber ride away from the hotel, there was a little bit of fun night life. I got to experience my first time seeing pretty much everyone else in the bar play on stage at some point in the night, though the main act was Mike Freund Band, in a random bar called Nighthawks, which was… interesting. But as the night went on, the musicians got better and better, so I guess the changeup works! They also has a taco truck out back but the bartenders didn’t recommend it and none of the patrons were using it, so that was a no-go.

After a little music, it was on to food, and a recommendation from a vegan on the street led to a trip to a local bar called Kickbacks, which apparently had amazing vegan nuggets. I was skeptical, but those nuggets turned out to be the best part of the meal that night, out of everything else ordered! Now I’m a fan!

The next day before making the drive to St. Augustine included a stop for lunch at Olio Restaurant. Not being crazy hungry, I just got a salad and soup, but the most interesting thing here was the ginger ale – they give you real ginger syrup in a cup and you add soda water at the fountain. It’s the best ginger ale I’ve tasted in my life and I definitely want to replicate it at home!

St. Augustine

While not a location I would have picked to visit, St. Augustine turned out to be a fantastic place for a weekend getaway! I visited for a wedding held in the White Room, and stayed for a little extra time to check out the city.

The White Room

I didn’t know much about St. Augustine before this trip, and was happily surprised to find a variety of fun bars, shops and music venues! One of the favorite stops was Prohibition Kitchen, which seemed to always have great bands to lure you in from the street.

Prohibition Kitchen

I was also able to try Pizza Time, which claims to be ranked the 2nd best pizza in the US on Trip Advisor. I was skeptical, but after two slices, I’d rank this as the best pizza I’ve ever had – even outranking pizza in New York! The pizza here has set the bar for New York style for me now, and I’ll be on the lookout for something even close to this, nearer to home.

Pizza Time

Joining a pub crawl also allowed for finding some fun spots around St. Augustine, including:

Ancient City Brewing
Nice variety of craft beers for fairly low prices

Ancient City Brewing

The Backyard
An ideal gathering spot with fun drinks, perfect for a small group

Painkiller at The Backyard

No Name Bar
A fun spot that gets crazy crowded at night, with good live music

No Name Bar

The White Lion
The cheapest drinks in the city and live music on the patio

It was also a great time walking around and learning a little bit of history about St Augustine. I highly recommend the Historic Pub Crawl from staugcitywalks.com if you’re looking for a fun intro to the city and some hot spots to hang out in during your visit! Lenny was a great tour guide and really knows the area!

I am so happy to have been able to spend a day exploring St. Augustine – I was pleasantly surprised at how much I enjoyed the city. It reminds me of a smaller version of Savannah and I wouldn’t be opposed to a repeat visit for a long weekend to explore even more!

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