Ever wonder what it’s like to spend a weekend in the Oldest City in the U.S.? A family weekend in St. Augustine is the perfect getaway to experience rich Florida history, great food and drinks, and scenic views all within a quaint walkable town.
We took the kids on a quick weekend road trip to the coast as an end of summer adventure. It was a one-night stay in the city, but we made the best of every minute. Here’s what a family weekend in St. Augustine looks like.
We hit the road early on Saturday morning and checked in at the Casa Monica Resort & Spa. This resort, established in 1888 and restored in 1999, is recognized by the Historic Hotels of America as one of the Most Haunted Hotels and is located in the heart of St. Augustine.
What to do on a Family Weekend in St. Augustine
It’s in the perfect location to experience everything, and the ease of being able to walk everywhere, especially with the kids, is the best way to explore. The Old Town Trolly Tour is also a really popular option to explore further and get an even deeper history of the area. Because we already knew what we wanted to see, everything was so close and we decided against it for this trip.
Once we arrived, we took a short walked along the water to the Castillo de San Marcos.
We explored for a while (in the heat!) until the cannon firing demonstration which was very cool.
There was a nice sea breeze though so that was a plus.
Afterwards, we were ready to cool down and find a lunch spot. We were meeting with my good friend, Loreyn, and her family who live close by.
Exploring St. George Street
The best options to grab a bite are located on the famous St. George Street. We put our names in at Prohibition Kitchen while we walked around a bit more. Then, we discovered an indoor mall with the iciest air flow and followed it like zombies. To our delight, Barefoot Bill’s greeted us at the end of the hallway and we grabbed a drink while we waited.
PK was a great spot, with a really cool vibe and great food. The kids had fun with the best kids menu activities I’ve ever seen. We decided to keep it light with apps, since we had early dinner plans.
Some of our other top contenders for lunch that were all in walking distance of the fort were:
It’s so hard to go somewhere for only a day, because we don’t get to eat that much! And that is one of my favorite parts.
All Hands on Deck, Maties!
After lunch, we went to the Pirate & Treasure Museum, which has been on my bucket list for this year. I’ve always thought that pirate stories were the most intriguing, so this was just as exciting for me as it was for the kids.
There were some very cool experiences throughout and so many rare artifacts. The kids had fun on the scavenger hunt, searching little secret drawers for all the items. And we of course let them pick out a “treasure” from the gift shop before leaving.
Afterwards, the guys found a great spot, called Pierre’s Pub, with fans and live music, while Loreyn and I found the kids some sweets.
There were so many ice cream shops along the main street. But we stopped by these two locations to get our sweet on:
Earlier in the day when we were looking for a spot for lunch, we put our name in at River and Fort, a new steak and seafood restaurant right outside the Castillo on the water. It worked out perfectly to get back for dinner since they only take walk-ins and the wait was super long.
It was a really pretty place and the food was really great as well.
After dinner, we went back to the hotel and let the kids chill for a bit. It was so much fun seeing our friends!
After our rest, I still wanted to explore the city a bit after dark. We headed back out to St. George Stree and came across some great live music at Colonial Oak Music Park. And when the kids were no longer capable of standing, we went back to the hotel to settle in for the night.
Sunday
On Sunday morning, we made our way over to Blue Hen Café, a place on my must try list. It was a 12 minute walk from the hotel—a bit long for the kids, but we made it, alright. It was in the opposite direction of where we were on Saturday, so it was fun to do more exploring.
There was—of course—an hour long wait when we got there, but we put our names in anyways. We needed our coffee so we headed back to the hotel to grab Starbucks. It ended up working out great, because we walked to the Flagler College on the way back. It’s a historical landmark and the kids really enjoyed it too!
There is still so much we want to see, but this was a short trip. We would love to take a tour of the school next time. It was definitely hot enough for the pool or beach, which we didn’t make it to either.
Ancient City Brewery, the Distillery and Ice Plant Bar were missed because we had to drive home after breakfast, but are definitely still on the must see list. It was a great family adventure in St. Augustine and an experience both adults and kids will remember.
Wow! Great trip!