A Perfect Family Weekend In St Augustine Florida

We had an amazing trip to St Augustine Florida for a Labor Day family getaway from Cocoa Beach. We stayed for the holiday weekend and crammed a ton of activities in.  Through the weekend we strolled through St George St, Visited the Castillo De San Marcos, The Lightner Museum, The St Augustine Lighthouse, Whetstone Chocolate Factory, and even had a beach day. We also had the chance to eat some tasty food at several places throughout the area.  

St Augustine is the oldest city in the United States established in the mid-1500s! Its located on the East Coast of Florida about a 2-hour drive from the Orlando and Cocoa Beach areas. We drove up after work from Cocoa Beach Friday and arrived at our Airbnb at about 7:30 PM. You can check out the place we stayed and even book it yourself at the bottom of this post. 

Where we stayed

Darrel and Dee’s place was perfect for our family of 6. Everything we could need was available and we were only about a 3-5 minute car ride for decent parking within walking distance of the Castillo. You are also about a 15-20 minute drive to the beach depending on traffic. 

The walk to the center of town will take you about 20-25 minutes which is perfect for adults and teenagers. It was just a little much for younger ones. You have to cross an extremely busy highway and even our bartender at the Floridian said it was dangerous.  We took an Uber into town and walked back when we had a kid-free night and it was an easy walk by ourselves. 

Within a two-minute walk, there is an awesome brewery and they had this guava mango IPA that was probably the best beer I have ever tasted. Communication with hosts was perfect and check-in was a breeze. I highly recommend this cozy little cottage if you are staying in St Augustine.  

Our First Night

Once we arrived in St Augustine we checked into our Airbnb. This first night we took this walk where we learned about the three-mile round trip to and from the center of town. We got the lay of the land, strolled through Flagler College which was stunning. It reminded me of the castles out of Harry Potter. We strolled through St George St and then to the Castillo De San Marcos. It started getting dark and because we were not familiar with the area we played it safe and walked home. 

Day One The Lightner Muesum And The Castillo Lawn

Saturday we got up at a semi-decent time, had some bacon and eggs for breakfast and some coffee. We decided instead of the walk we would try to park downtown to be closest to the center of everything. Driving we initially attempted to find the city parking which is scattered throughout the city. All of the city parking that we could find seemed full.

We then saw a sign for $15 all-day parking at the Villa Zorayda Museum. The lot attendant was extremely nice and gave us a ton of information about the area. We then walked to The Lightner Museum to start our first activity of the vacation. 

Walking up to the Lightner Museum

The Lightner Museum is within the historic Hotel Alcazar building in downtown St. Augustine. The hotel was built by Henry Flagler, to appeal to wealthy tourists who traveled south for the winter on his railroad, the Florida East Coast Railway. The building is stunning and was made by the same architects that designed the Flagler Collage. 

While it was a hotel they had a steam room, massage parlor, sulfur baths, gymnasium, a three-story ballroom, and the world’s largest indoor swimming pool! The swimming pool now actually holds a restaurant in the empty deep end called Cafe Alcazar. Several years after the stock market crashed the hotel closed down. 

In the mid-1900’s it was purchased by Otto C. Lightner and turned into a hobbies museum that even had his own personal collection of art in it. Shortly after the city of St Augustine took it over and it opened to the public. 

The Famous Fish at Bantam Chef St Augustine Florida

After the museum we knew the kids would be hungry, so we planned for a fairly affordable dining option close by. There is the Alcazar Cafe which seems to have a decent menu but is not necessarily kid-friendly or affordable.  Directly across the street from the entrance of the Alcazar Cafe is the Bantam Chef. I found this place looking on Instagram and google maps prior to our visit. 

The Bantam Chef is known for its Famous Fish. It is this MASSIVE sandwich with layers of crispy flakey lightly battered and fried fish, lettuce, tomatoes, onions, and a lightly flavored tarter sauce. All of this housed between two perfectly grilled buns. This beast of a sandwich was amazing and only 9.95 a person! 

Famous Fish at the Bantam Chef

The kids had burgers and chicken tenders and they ate everything. It was priced well at about $60 for all 6 of us with drinks. My only downfall is that I think we forgot to order fries with the burgers as they only got a burger and for two teenagers that is not really enough. Overall I highly recommend The Bantam Chef specifically for the Famous Fish. 

I am surprised this place isn’t more known. It is kind of in an awkward spot that’s a little off of the beaten path. And those are usually the best places to grab a bite to eat. 

Exploring St Augustine and the Castillo lawn

After eating we headed towards the Castillo De San Marcus. We have a habit of taking the back roads and avoiding the main strips. I mean who really likes traffic, even of the pedestrian kind. I do have some advice about walking in St Augustine. A large number of the streets and always are shared by both pedestrians and cars. 

Being that we had 4 children with us this can be a little intimidating, that’s why we suggest trying to park close to where you are planning on visiting. The reason for the feeling of caution walking with the kids is most vehicles on these streets are driven by tourists. So before heading to your destination try to map out your route and where you will attempt to park. Also, be very aware that most streets are one way. 

We headed along the waterway in an attempt to look at the Pirate Ship that does several shows on the water. Unfortunately, it had already headed out and wasn’t docked. So we walked to the Bridge Of Lions. This is really a beautiful sight in itself, although a reason for a majority of the traffic. Being a Mainstreet going to the beach, it also raises and closes at least once an hour. Not a worry when you are going on foot though. 

We finally made it to the Castillo and the line to go inside was extremely long. We are talking liking 70 people long, I think a tour bus had just dropped some guests off. 

We like to avoid the crowds and lines so we decided not to go in on this day and schedule it for another time in the trip. So we wandered around the outside which is completely free to do and very entertaining in itself. The kids had a blast playing in the fields of this historical fort. It’s a really awesome feeling wondering these grounds and takes you back in time. 

They even have some cool things on display outside. One thing I found awesome was this stove-looking thing that was used to heat cannonballs. The purpose would be to hopefully catch the enemy’s ships on fire. I don’t think they actually ever uses it and it served another purpose instead. 

We then wandered over to St George St which is probably one of the most publicly crowded places in St Augustine. You have hundreds of shops stores and be warned if you have little ones. The number of candy and sweet shops is absurd. It was fun for a quick stroll with the kids but having explored a museum and a fort they were ready to call it for the day. 

We had planned on having one night out with just mom and dad. Even though we were exhausted we made the best of our time and made a date night happen. For the kids, we ordered pizza from a place called 5 Star pizza. There was another one with a higher rating called Carritos which was appealing. 

5 Star Pizza St Augustine Review

5 Star just seemed to be less known. So as always I went with the off-the-beaten-path. I called in the order and they had a special of a 1 topping 16-inch pizza, and 10 wings ( we chose barbecue) for $24.99 so I jumped on that. They also had a 24-inch pizza called the Piezilla. The girl that took my order was super friendly. 

Normally the kids dont eat anything other than cheese pizza, so when she asked what toping and I said none for the first time in my history of pizza ordering something outstanding happened. She suggested I just choose extra cheese. My mind is blown, I know it’s something simple but I mean it’s extra cheese. 

They also told us the order would be delivered in 30-40 minutes. We were surprised that when the delivery driver showed up in 20 minutes. It was actually comical as the younger ones open the door. I of course yelled at the kids not to open the door but the driver was extremely nice and funny about it. 

Date Night In St Augustine Florida

I tried the pizza and it tasted really good, not amazing but good quality and tasty. Once the pizza was present and the kids baby sitter was situated we ordered our uber. It took about 15 minutes to arrive and had us downtown in about 5 minutes. I believe the total was $16 plus a tip. Once we were in the downtown area we chose to go to Casa De Vino 57.

Casa De Vino 57

We chose this place as we just wanted to have a light snack and just a drink or two. The place had a nice outdoor setup and live music playing. We enjoyed two glasses of wine and the smoked fish dip. The smoked fish dip was from a local market and was really tasty. After Casa De Vino we decided we would head towards a place for dinner. 

We decided we would try Collage which is a high-end restaurant that had amazing reviews and numerous recommendations. Unfortunately, they were reservations only so we were turned away at the door. So we wondered and the only place that seemed to be available was The Floridian. 

They had a 20-minute weight for a table, but fortunately for both of us, they had two seats available at the bar on a first come first serve basis. Jess and I enjoy eating at bars one because of its fast service, two it gives you a chance to chat with the bartender about the area. As well as get some really good advice on what to order. 

Restaurant Review Of The Floridian In St Augustine Florida

I will be honest the Floridian was really not on my list. It comes highly reviewed and recommended, but from my research is its a rather touristy very well know spot. I try my best to find the hidden gems when it comes to restaurant’s and living in a tourist town myself I know the quality drops in most restaurants of this style. 

So going into this experience my expectations were low. Our Bartender Andrew was excellent, very insightful about the menu as well as the area. He steered us away from several dishes which looked and sounded appealing. After he described them and the cooking process I was very thankful as I probably would not have eaten my food if I went with my original order. 

We went with the fried green tomatoes that were “cornmeal-dusted served over spinach with green tomato relish, house-herbed ricotta, and basil aioli.” I dont recall the tomato relish or the spinach. They were ok but I am not a fan of the cornmeal batter and they seem like they were rushed through the batter process and then fried too long on top of it. 

For our main dishes, we had 


Braised CartWheel Ranch beef brisket over aromatic rice and a zesty roasted green tomato, field pea, corn, and pepper ‘Posole’. Finished with datil jam, pickled onions and cilantro, and corn tostadas for scooping


House creamed corn, peppers, poblanos, cherry tomatoes, and cheese, cooked down with aromatic rice into a rich Creole ‘risotto.’ Served with sautéed shrimp and local sausage, topped with roasted Tomato + Pepper + Corn Relish and herb Gremolata.

Both were tasty just not anything to rant and rave about. The rice on both dishes had that dry bland out-of-a-bag taste, and the entrees were over seasoned. I’m not talking too much salt, I mean they added way too many flavors to it. Which made it hard to distinguish what was going, the opposite of keeping it simple with quality ingredients.  

Don’t get me wrong the food was edible and we ate all of our leftovers, I did not finish or pack the tomatoes though. Overall though for an appetizer two entrees and a bottle of wine at $90 combined with actually getting to sit and eat on a Saturday night I can’t give this place a bad review. It was priced fair and the food was good. 

We decided we would walk home and on the way stopped at Bog Brewing which was directly across the street from our Airbnb. I had the Brett’s Beach House IPA which was amazing!!! Probably one of my favorite craft beers that I have tried yet. It was a hazy IPA with lots of citruses and a strong taste of Mango and overripe Papaya. 

The beer came in at a whopping 7.5% but drank extremely easily and light. I had two and let’s just say it was a good thing I only had one street to cross to get to our Airbnb. Once home we went straight to sleep to be ready for our next day.

St Augustine Beach and the Lighthouse

Being we were trying to stay budget-friendly we thought a beach day would be perfect. So we went to St Augustine Beach towards the south area. We packed a small cooler with drinks and sandwiches already made as well as some snacks like chips and cookies for the boys. The beach was really nice.

I will warn you though that the sand in the area is very shelly. It has a tendency of really sticking to your skin and I one of the harder types of sand to wash off. We parked at St Augustine Beach by the pier and it didn’t take too long to park. It was also free and they had a really cool splash pad that was perfect for after the beach. 

We spent several hours playing in the water and building sandcastles and just relaxing. It was a really nice time. One thing I do say is on any beach always fill in your holes when playing in the sand. If you don’t it hurts that sea turtles during nesting seasons. The mothers can flip over and get stuck and will perish if not rescued. Anyways other than just caring about the turtles and environment enjoy your time. 

While the kids were playing on the splash pad we contemplated dinner. There were a couple of highly-rated restaurants close by, but they all seemed busy and appeared to be possible tourist traps. For Jess Crab Legs are a must, so I went to a Facebook group called I Love St Augustine Florida and searched. A place called Caps on the water was mentioned by locals in the group numerous times for the best seafood in the area.

We then packed up the kids from the bach and headed toward caps on the water which was on the North Beach of St Augustine. So we had to drive over the bridge of lions past the Castillos and back over another bridge to the north beach area. While we were still on the south side we did stop at the St Augustine Lighthouse to get some pictured from the parking lot. 

St Augustine Lighthouse

We finally made it out toward caps on the water, but something happened at the restaurant, and a fire truck and an ambulance had to come in for an emergency. So we had to adjust our dinner plans. Good thing I always try to have a backup plan when it comes to eating out, especially with hungry kids in tote. 

Restaurant Review Aunt Kates

My backup plan was Aunt Kates which was only a couple of blocks away, still had seafood, and was on the water. This was a great choice and actually a welcome change as they were a little more on the casual side. There were numerous people with families around and the fact that we felt welcomed in our beach clothes was a plus. 

The weight was about 20 minutes which was absolutely fine. The area of the restaurant is attached to some public docs and water entry for boats to the St Johns river. So we walked the river’s edge and enjoyed the beautiful scenery as we waited for our table. Once we were sat our server was on point from start to finish. 

Our oldest ordered the Trio Salad which was Crab salad, chicken salad, and shrimp salad served with fresh fruit. He said it was really good! Youngest went with the standard chicken strips and fries. Our other picky little eater decided he wanted to order the BBQ ribs which came as a complete shock to all of us. We did not argue and just rolled with it and he demolished the ribs. 

We also had some Ahi Tuna and Gator bites, She Crab Soup, and two low county boil’s. The tuna was ok and came with sweet chili sauce drizzled over it. The sauce seemed like the pre-mixed jar sauce that you can pick up at any store. The gator bites were kind of meh and also had that cornmeal batter that we discover we really don’t like. 

The low country boils were super fresh and tasty, the crab legs were very fresh just on the smaller size. Th crawfish were huge and tasty as well as all of the other seafood. They also bring out this bread basket at the start of the meal that is amazing. It’s an assortment of freshly made cornbread, pumpkin bread, and some other ones. 

With the amazing view, tasty food, and awesome service in a family-friendly environment, I HIGHLY recommend Aunt Kates in St Augustine. After dinner, we headed home for the evening so that we would be ready to check out on time the next day. 

The Last Day in St Augustine

One thing I dislike about traveling is the check-out times always being like 10 AM, I get it and understand why. That does not mean I have to like it. Check-out was simple and easy at the Airbnb. We still had Monday off with the kids so wanted to enjoy as much of St Augustine as possible so planned to stay in the area after we checked out.

The Donut Experiment

First, we hit up The Donut Experiment This is a coffee and donut shop with wifi lounges. They make the donuts per order and you can see the machine flipping them to fry the donuts. The dough was out. So they had to make the fresh dough when we got there. Good thing though as we got the first batch of new dough for our donuts. 

We ordered an assortment of donuts, the possibilities are limitless. You choose your frosting, followed by topping, then your drizzle. We went with some of the “popular” choices, Boston cream, key lime pie, and some oreo and chocolate chip. The donuts were excellent and absolutely jam-packed with sugary teeth chilling goodness. 

Then we headed to the downtown area with the goal of going inside the Castillo De San Marcos. Our timing could not have been better. We immediately found the city’s paid parking spots available. For this parking, you enter your license plate number in one of the meters and pick how long for. We chose the 4 hours and I think it was like $14 dollars. 

Going inside the Castillo San De Marcos

From our parking space to the Castillo it was only a 5-minute walk. Once we got to the Castillo there was not a single person in line. So Monday morning at 10 AM is a good time to visit this historic fort. The kids were free and Jessica and I had to pay $16 a person. Not bad at all. Also, a money-saving fact is that this is a National Park. So if you want to for like $70 you can get a national park pass that gives you access to anyone in the entire United States. 

We have Canaveral National Seashore close to where we live and are contemplating buying the pass for our family. Then we could make the drive to the Castillo whenever we wanted!

We were beyond happy that the place wasn’t crowded so we headed into the Castillo San De Marcos. This is the oldest masonry fort in the US  and was built by the Spanish in the mid-1600s. The building is beautiful in grey coquina rock. You can feel the history of the place. Seeing the canons and motors while walking the walls that soldiers stood defending centuries ago. It really is an amazing experience. 

The park rangers are super friendly and provide you with a wealth of knowledge. When you enter the fort you can explore the rooms of the lower levels. From the minutemen quarters to the jail cells it’s really cool. The kids loved it as did Jess and I.

After about two hours of exploring the inside of the fort, we headed out for lunch. Our plan was to do a tour at the whitestone chocolate factory if possible. The tour includes chocolate samples so we knew it would be a good idea to grab some “real” food. Our older boys are cheeseburger fanatics. So when I was researching family-friendly places to eat I came across One Twenty Three Burger House. 

Restaurant Review: One Twenty Three Burger House

We arrived at One Twenty Three Burger and lucked out finding parking. This was great as it’s one of those really tight-spaced parking lots. We were seated within seconds of entering and right away you could tell the service was going to be top-notch. 

Our waitress was instantly accommodating, listing all of the kid’s drinks right away. This helps when you have little ones that don’t all drink soda. Much better than the typical “we have Coke or Pepsi products”. Both Jess and I ordered burgers with sauteed onions, mushrooms, bacon and topped with an over-easy egg. 

Jess is not a burger fan, but she absolutely loved this thing. I thought it was really really good as well. Honestly probably one of the best burgers I’ve had. I did a little research and found this video of Burger One Twenty Three That Explains why the burgers are so good. The reason being is they use a higher grade of beef. So when you bite into the burger you are tasting the meat. 

This couldn’t be more true as even though it was topped with some flavorful goodness all you could focus on was the meat. The depth of flavor and perfect texture consistency through the burger patty was on point. I even ate the burger a day later and it was still delicious. The service was out of this world as well, not only did the waitresses help and vibe with each other, what appeared to be the manager was going around and checking on all of the tables. Even the food runner was extremely friendly and personable. 

Overall this is an amazing experience, and if you are a fan of burgers it’s a must-do while in St Augustine. 

The Whetstone Chocolate Factory Tour

During our lunch, we purchased our tickets online from the whitestone chocolate factory. We headed straight there from Burger One Twenty Three which is right up the street. As an adult the chocolate factory tour was ok, but for our youngest two, they loved it! Absolutely recommended for children 4-8 years old. 

The tour was about $55 for all 6 of us and lasted about an hour. You start off in a waiting area that has I love Lucy’s chocolate factory episode playing. There is also a statue of Lucy in the same fashion as the episode. Here the guide introduces themself and The White Stone Chocolate factory story. 

After the first room, you head into another area with a TV presentation that goes in-depth about the Cocoa Bean and its process to becoming chocolate. The Video was an old 90’s, probably still on DVD and originally made on VHS video. As corny as it was, our youngest LOVED the video, and then we got more chocolate. 

We then walked out of the building and crossed the parking lot to the factory. The factory was really cool, with lots of moving parts and chocolate being made. Not anything like Willy Wonka but pretty cool. Here we had another sample that was packaged right in front of us. It was one of those tasty orange chocolates.

We then ended the tour with one last sample. The super dark chocolate, that was so bitter. I don’t know if this is so you crave the good stuff exiting through the gift shop or if it’s a palate cleanser. Either way, the expression on our kid’s faces made it worth it. In my opinion, the last piece would be amazing with a glass of wine. 

After finishing the tour, we hopped in the vehicle and went on our way back home to Cocoa Beach. We had an outstanding weekend in St Augustine and accomplished so much. The Castillo was one of my favorite experiences, we had a fun beach day. Enjoyed lots of walked old city streets ate great food and toured a Chocolate Factory and the LIghner Museum all while in America’s Oldest City St. Augustine. 



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