How to See St. Augustine in a Weekend: Where to Go & What to Eat


About a month ago, Nate and I were able to finally go explore St. Augustine and I can’t believe I never shared the experience with you! The last time we planned this trip was last October and of course Hurricane Matthew had to roll in and ruin everything! This time, we made it a weekend trip and had an absolute blast. Keep reading for our guide to seeing St. Augustine in a weekend!


Some of the best trips are those that you just randomly decide to go on and this one couldn’t have been more fun. It was one of those moments where we were pretty much kicking ourselves for not going sooner!

We kept hearing from people how St. Augustine was one of the most beautiful cities in all of Florida and the fact that it’s the oldest city in the United States just added to its allure. We had been reading up about all the awesome things to do and our only problem was trying to figure out how we were going to see it all!


I knew it would be pretty warm but I also knew that we’d be doing a lot of walking so I had to wear shoes that were not only cute, but comfy and easy to walk in. I opted for these colorful tie up sandals from Schutz. I bought them for my honeymoon last year because I knew we’d be doing a lot of walking in Las Vegas and I’m still wearing them this summer because the quality is so good!

These work so well when you’re traveling in the spring or summer because they go with literally everything you could pack. These are the only shoes I brought to St. Augustine because I knew they would serve me well!


These photos were taken at Flagler College coincidentally on their graduation day! It was so cool getting to see the graduates taking pictures right next to the gorgeous fountain right in the middle of the courtyard! Nate even got a photo of the ceiling on the inside (below) because we couldn’t believe just how beautiful the art and architecture was there!

Nate and I drove in on a Saturday morning (we’re only an hour and a half away) and stayed until Sunday afternoon. The night before we left, we took a friend of mine’s advice and booked two tickets for the Ripley’s Red Train Tours, which cost about $21 per one day ticket and it runs from 8:30am-5pm and goes to about 19 different locations. Seeing as how you can get on and off as you please whenever you want and join up again later was appealing to us, considering we kind of wanted to do our own thing, so we booked this tour.

What’s cool is that the different drivers/tour guides take you on a traveling tour past each of the locations if you stay on in the loop the whole time. So it pretty much pulls double duty as you find out interesting facts about the city while hitching a ride to your next destination. We used this service starting at the actually Ripley’s Believe It or Not Museum (where we parked) and rode it on and off throughout the day.

So, here was our schedule of what we did the entire weekend!

How to See St. Augustine in a Weekend

Day 1

Castillo San Marcos

1 S Castillo Dr, St. Augustine, FL 32084

This was our first stop and cost us $10 each to get in and explore all it had to offer. It’s our nation’s oldest National Historic Monument as it was built by the Spanish starting in 1672 and much of the original still stands strong today despite countless attacks. We were able to see reenactors fire off a cannon (to recreate what they did during the battle of 1740 against the British). It was a lot louder than I expected, but it was awesome to see. There are a ton of things to do there to besides just walking around. There were several reenactors in different areas of the structures explaining how they lived back then and showing us how they lived, etc.–very cool to see!

Flagler College

74 King St, St. Augustine, FL 32084

Built by railroad tycoon, Henry M. Flagler in 1888, the Ponce is considered one of the the most beautiful examples of Spanish Renaissance architecture and was one of the most exclusive resorts of its day. Our tour guide from the Red Train Tours told us funny stories like how they were the only business to have electric lighting and so they would brag about it and put it on at night so they could gloat while the rest of the city didn’t have it. Like I said before, we didn’t pay for a tour or anything, but we got to walk around outside and in the lobby to see some of it and hear some history. It is truly a beautiful place and a staple in St. Augustine. This is definitely a must-see for the architecture alone. Tours usually run from 10am-3pm and cost about $10 a ticket.

The Oldest House

This is one of those things we heard a lot about through our train tour but didn’t get a second to actually go in it! I would love to go check it out next time.

The Fountain of Youth

11 Magnolia Ave, St. Augustine, FL 32084

In my opinion, this was one of the coolest things that we did because you got so much “bang for your buck”. Deemed the “original 1565 site of St. Augustine” this park was first explored by Juan Ponce de Leon in 1513 and settled by Pedro Menendez de Aviles in 1565. According to the website “Colonial America started right HERE, 55 years before the Pilgrims landed on Plymouth Rock, and 42 years before Jamestown”. One of the best parts about this park would be all the wild peacocks running around. They let you get so close and it was unbelievable to see! We went around mating season so it was hilarious to see all the male birds “putting on a show”! They have what’s said to be the actual “Fountain of Youth” inside of a historic museum-like exhibit where you can actually grab a cup and drink from it or run your hands through it. Pretty cool. As we kept walking through the park, there were docks that extended into the bay where Native American villagers originally lived. I thought it was pretty awesome that they had a reconstructed version of the First Mission of Nombre de Dios where the first Christian Indians attended mass in 1587. They also have blacksmith demonstrations and things of that nature that reflect life back then. Also, on our way out we were able to see the gigantic (I mean, it’s incredible!) oak tree named “The Senator” that is said to be over 600 years old! Tickets to the park are $15 per adult and in my opinion, definitely worth every penny!

Lunch at “The Backyard” at Meehan’s (Island Bar)

20 Avenida Menendez, St. Augustine, FL 32084

We got back on the Red Train Tour and found a cool place in the middle of the city to have lunch. We wanted to eat outdoors, so we found this joint which offered cold beers and a fun take on island food. I got garlic wings and Nate got tacos. The restaurant is a part of a bigger and more famous bar/restaurant called Meehan’s Pub, which we were able to see later during our Pub Crawl.

Hyppo Gourmet Popsicles

48 Charlotte St, St. Augustine, FL 32084

I’m probably preaching to the choir here if you’ve ever been to a Hyppos but this place takes the cake (or the popsicle?). This was right across the street from our lunch spot and we were drawn in by all the colorful signage and the menu outside. We went in to see over 50 original flavors of gourmet popsicles and couldn’t wait to eat one! I ended up getting the prosecco pear marscapone and Nate got blackberry goat cheese–they sound weird, but were heaven…trust me.

The Oldest School House

This was really cool to see because I’m a teacher. It was believed to have been built around 1716. There are paid tours, but we did the walking tour (I’ll talk about that later) and learned about it more later on in the evening.


21 King St St. Augustine, FL 32084

This was the cutest little boutique in the city and I found beautiful necklaces that were affordable, too! I loved the boho vibe–it was like a more affordable Anthropologie!

Dinner at The Floridian

72 Spanish St, St. Augustine, FL 32084

The Floridian was an excellent restaurant recommendation from a friend on mine in Orlando and let me tell you– it delivered!! The amazing farm to table food tasted so fresh and the combinations were unique and quite tasty. They only use seasonal local ingredients in their food.

Here’s what Nate and I got:

Choice of grilled fresh catch, FL shrimp or tempeh over arugula tossed with pan-toasted cornbread croutons, heirloom cherry tomatoes and sweet pickled onions with Thomasville Tomme Cheese, and a drizzle of basil-buttermilk dressing.
Vine-ripe tomatoes and goat’s feta layered over fresh spinach and topped with crispy CartWheel Ranch pork belly, radishes and an African sweet bread toast schmeared with creamy Lil Moo cheese, slow cooked Bacon Jam, basil, and S&P heirloom tomatoes. Served with garlic-bacon vinaigrette.


The Social Lounge

59 Cuna St, St. Augustine, FL 32084

If you follow me on Snapchat (@mdamon21) you saw me snap tons of this little bar. It’s a tiny house with a bar built inside! I had a glass of wine and Nate had a local beer. They had a couple of TVs and a boatload of board games for people to play–we played Jenga!

“Spirits with Spirits” Paranormal Pub Crawl

This was one of the highlights of the trip for us! For under $20 a ticket, we had a 3 hour “haunted” pub crawl where the first drink was provided at a bar called Prince of Wales, where our group met up. It ended up only being us and another younger couple on the tour with our tour guide so naturally we had a blast. We had a walking historic tour of the city at night and the places that were haunted based on historical events that occurred. Over the course of the night, the guide has us go through the city outside and 4 other bars with ghost meters that measured paranormal activity in milligauss (mG). It was crazy seeing that thing light up when we sat in a bar that two soldiers were apparently buried under us!

Day 2

The Old Jail

167 San Marco Ave, St. Augustine, FL 32084

We drove by this with the tour guide in the morning the next day and found out that it was built by the same people as those who built Alcatraz and housed the same types of criminals. They even carried out capital punishment there. It started as a museum in 1954.

Ice Plant for brunch

110 Riberia St, St. Augustine, FL 32084

The industrial-style building is gorgeous and kind of hipster in vibe. It has even more local farm to table food in interesting and yummy combinations (seems to be the theme in this city!). I got the Eggs Benedict on Crispy Local Fish Brandade with red pepper hash. Nate got the St. Augustine Shrimp & Anson Mill’s Grits with fennel sausage, corn, okra, and tomatoes. Sidenote: their craft cocktails are to die for. 

St. Augustine Distillery Tour

In the same building is the St. Augustine Distillery complete with a free tour where they show you how they make their gin, whiskey, and rum! You get free samples as well and they even make you sample cocktails they’ve crafted.

St. Augustine Lighthouse and Museum

81 Lighthouse Ave, St. Augustine, FL 32080

A little drive away from the city is the famous lighthouse which I was terrified to climb! The view was gorgeous though, even if it was a bit windy! Tickets are $12.95 per adult and the museum comes with the price of the ticket.

Anastasia Island

Anastasia Island was about a 20 min drive outside of the lighthouse museum and so worth it! I wish we could’ve stayed longer but it was so incredibly windy we knew a storm would be rolling in.


Well that’s that! I can’t wait to go back again and next time hopefully with family and friends so they can experience it as well! If you like a laid back town with tons of history and amazing food–this is your city. It has quickly become our favorite here.

Have you been before? What would you add to this list?



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2 Comments on How to See St. Augustine in a Weekend: Where to Go & What to Eat

  1. Chaundra
    July 13, 2017 at 9:30 am (2 years ago)

    Loved this post, the first time I ever went to St. Augustine was when I was 9 or 10, it was the first time I met my soon to be stepmom. One of the favorite things, was going to the chocolate factory to get some fudge. It was delicious! It was also the first time I realized how funny she was, she mooned me and my sister when she was saying good bye to my dad.

  2. Missy Damon
    July 14, 2017 at 10:08 pm (2 years ago)

    It’s so much fun! I loved going there. I never knew what I was missing!

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