The Ultimate Guide to St. Augustine, Florida

Jennifer MeyerDestinationsLeave a Comment

Lightner Museum St. Augustine, Florida

History of St. Augustine

St. Augustine is a quaint city with a small town feeling. The city has many historical sites and is quite proud its heritage.

(The following information was retrieved from Visit St. Augustine)

St. Augustine was founded in 1565 by the Spanish. Even though Florida was discovered 50 years earlier, the Spanish had no interest in colonizing until the mid-1500s.

Still, St. Augustine is the oldest continually inhabited European settlement in the US.

Through trial and error, the Spanish eventually settled in the current day historic district of St. Augustine.

In 1672, they began building the Castillo de San Marco. The fort was under construction for 23 years. However, it ended up being time well spent. The material they used to build the fort, Coquina, and the location at which the fort was built ended up being ideal. They made good use of the fort shortly after it’s construction when under English attack.

If we fast forward a couple hundred years, we come across another important milestone in St. Augustine’s history. In the late 1800s, Henry Flagler, one of the richest men in America at the time, decided to start the Ponce de Leon hotel in St. Augustine. He spared no expense in construction since the hotel was meant to be a luxurious hotel. Flagler also expanded the railroad, bringing it all the way down to St. Augustine. This made travel for guests much easier. Flagler is one figure who is at least partially responsible for making St. Augustine the city it is today.

If you would like to read more about St. Augustine’s history, you can read a complete history at Visit St. Augustine’s website.

Where to Stay (I’m Sleepy!)

Personally, I have never stayed in a hotel in St. Augustine. I have stayed at a Bed & Breakfast once for a wedding, but that was a long time ago.

When I visit St. Augustine, I stay with friends.

If you don’t know anyone that lives in St. Augustine, don’t worry!

There are tons of Bed & Breakfasts that offer an intimate and homey atmosphere. Plus, they typically are in convenient locations!

Since I haven’t stayed at a Bed & Breakfast there in a long time, I cannot recommend a specific one.

But I am going to link you to You can use the link to search for Bed & Breakfasts for the dates you travel. has guest ratings for each Bed & Breakfast, so you are sure to find a great one!

Search for your perfect Bed & Breakfast here!

(Disclaimer: I do receive compensation if you book a hotel through the link provided above. However, I truly do like site and personally use it when looking to book a hotel!)

Historical Sites You Must See (Entertain Me!!)

When visiting a historical city, there is tons of stuff to see and do! Here are my 3 favorite things to see and do in St. Augustine.

Flagler College

Flagler College is a beautiful school. It is comprised of many of Henry Flagler’s buildings. Ponce Hall, where the women’s dorms are located, it actually part of Henry Flagler’s Ponce de Leon hotel. While many areas have been changed and renovated to accommodate a modern lifestyle, the college maintained much of the beautiful architecture.

While you can no longer stay there unless you’re a student, you can take a lovely tour, which departs daily at 10 am and 2 pm. For more information on tours, please visit Flagler College’s website.


Castillo de San Marcos

The Castillo de San Marco is an important piece of St. Augustine’s history. The fort is in amazing shape considering its age. Despite a few cracks and some dents, you’ll be amazed at how well it has been preserved.

Despite its great condition, you can definitely see the fort’s history just by looking at the outer walls facing the bay. There are actually dents were cannonballs struck it!

The fort also offers weapon demonstrations on the weekends. To get more information on times, check out the link below.

Get more information about hours and tickets at Visit St. Augustine’s website.


Ghost Tours

I know, I know. You’re thinking what the heck, lady?! A ghost tour is definitely not a historical site! And, you’re correct. However, the ghost tours take you around to many different historical sites. And unlike regular tours, you get fun ghost stories too! Don’t worry, you’re tour will be educational too. Before discussing the ghost story, the guide gives you a brief history.

I would definitely recommend Ghost Tours of St. Augustine. I went on this walking ghost tour back in July and thoroughly enjoyed it! There was a great balance of historical and spooky stories. This company often offers Groupons, so before you purchase tickets, check out Groupon for any deals! Just make sure you read the fine print!!!


St. Augustine Lighthouse

This lighthouse has quite the history! According to the lighthouse’s website, the St. Augustine Lighthouse was built in the same spot as an old Spanish watch tower. Pretty neat, huh? Plus, the lighthouse is rumored to be haunted! Although, I’m pretty sure they don’t mention that part on the normal tours; however, they offer a ghost tour of the lighthouse!

To learn more about the lighthouse’s history, you can visit the website linked above.

The visiting the museum and climbing lighthouse make a great afternoon activity. Here is some information about ticketing!


Places to Eat (Feed Me!!)

Everyone needs to eat. And on vacation, you want to eat well! Even if you’re trying to eat well on a budget, I have some great suggestions for you! Here is a list of my favorite places to grab lunch and dinner!

Classy Restaurants (For the extravagant traveler)


The Columbia offers traditional Spanish dishes with flair. Everything on the menu is fantastic, and the service is superb. Most recently, I ordered the Shrimp and Yellow Rice; it was amazing. Literally, the best yellow rice dish I have ever tasted!

Also, you should really enjoy some of their red sangria if you are of age. It is sweet and delicious!

Go ahead, take a look at the menu, I know you want to! Also, if you do decide to go, you should make a reservation! The Columbia is incredibly busy on the weekends!


The Floridian

Nearby the Columbia, there is a quaint, but impressive, restaurant called The Floridian. They take pride in offering culinary twists on classic dishes. I have heard great things about their Meatloaf Sandwich, South-East Fried Chicken Sandwich, and Shrimp and Grits. Personally, I have tried and loved the Shrimp and Sausage Maque Choux.

Oh, and whatever you do, Do. Not. Skip. Dessert. Seriously! I’m sure that all of their desserts are lovely, but you definitely need to try their Kentucky Derby Pie! They describe it as a cross between a chocolate cookie and a pecan pie. It is amazing! I don’t even generally like pecan pie, but I loved this!

Wanna check out their lunch menu and dinner menu? I know you do!


Harry’s Seafood, Bar, & Grille

Right across from the bay, Harry’s serves food inspired by its traditional New Orleans dishes. That means that their food is packed with exciting flavors! I personally enjoyed their French Market Pasta on my last visit!

The atmosphere is cozy. There is spacious outdoor seating available, which is beautifully lit up at night.

Menu? You got it!


Wallet-friendly Restaurants (For the savvy traveler)

Pizza Time

Pizza Time serves delicious authentic New York style pizza! The line can be long, but don’t let that deter you! Seriously, you definitely need to stop by for a slice. Just remember to bring cash, since this is a cash only establishment.

Want a menu? Well, too bad! There isn’t one available online. But you can find out more information and see pictures on Pizza Time’s website.


Burrito Works Taco Shop

While there isn’t tons of seating, this taco shop serves delicious tacos and burritos. If you can’t find a seat, take it to go! Find a seat on St. George Street and people watch.

With most everything under $10, you are sure to save some money even on the most popular street (St. George Street) in St. Augustine!

If you want to look it over, here is the taco shop’s menu!


One Twenty-Three Burger House

One Twenty-Three Burger House serves amazing burgers and wood-fired pizza. You wouldn’t think that a restaurant could make great burgers and pizza, but this place can! Plus, their french fries are incredible! I could honestly just order a bunch of their fries and be content…but I would never do that. Like, ever. 😉

If you want to see their menu, you’re out of luck. For whatever reason, their menu page isn’t working. But, if you’d like, you can read more about One Twenty-Three Burger House.


Where to Drink (Did Someone Say Booze?!)

The nightlife in St. Augustine is poppin’! That could be due the crazy number of tourists the city sees each year or it could be due to the college located at the heart of the historic district… Either way, there a tons of awesome places to check out. Here are my tried and true favorites!

Scarlett O’Hara’s

This bar offers happy hour all day everyday! There are a list of bears that cost $2-3 a pop. Super great price! If are a Sangria connoisseur, you probably won’t like theirs, but it’s only $3. If you’re casually drink Sangria like I do though, you might not mind it. There are also a number of liquors on special. Otherwise, however, their drinks aren’t overpriced. When I order a tequila sunrise with well-tequila, I am only charged $4!

On Mondays, they have Karaoke. So if you’re into singing, you should definitely stop by! You get a free shot (of whatever alcohol they are giving out that night) with every song you sing!

Learn more about Scarlett’s here!



If you like beer, cigars, and laid back atmospheres, you will adore Stogies! They are always changing out their taps, so there is always something new to try. Plus, a house cigar comes with each beer!

You can sit inside and listen to live music or play a board game. Or, if you’d rather, you can sit outside, where there is a fire pit for the colder months.


Dos Gatos

This is a slightly classier establishment. There is a dress code to get in; however, I don’t think it is strict. You just need to look presentable.

This bar is loud! On the weekends, there is a DJ, which means dancing! However, there is a lounge and bar upstairs, so you can escape the dancing if you so choose. The drinks here run about $10. Definitely try something on their cocktail menu. They have a lot of interesting drinks that you probably haven’t tried before. Here are some of the awesome cocktails Dos Gatos offers.


The Bar with No Name

Locally known as No Name Bar, this establishment offers some outdoor seating with a lot of indoor and outdoor standing room. It is a totally casual atmosphere. The bartenders generally know how to make a good drink, although they tend to pour a little heavily (not complaining).

On the weekends, they have live music or a DJ, so it’s a great place to hang out!

Plus, it has a great view of the Castillo de San Marcos!


White Lion

If you enjoy dancing, darts, or pool, you should definitely check out this bar! There is a huge dance floor and a stage where they either have live music or a DJ. Upstairs, there are some dart boards and a pool table. In order to get darts, you should ask your bartender for them. You’ll have to surrender your drivers license to the bar tender while you use the darts, but you’ll get it back as soon as you turn in the darts!

The drinks here are decent. They definitely pour heavily, and the drinks a pretty affordable!


I hope you guys enjoyed this Ultimate Guide to St. Augustine, Florida! If you have any questions, please leave them in the comments below.

Have you been to St. Augustine? Tell me about your favorite places to go in the comments below!

Go ahead, you know you want to learn more about other awesome Florida Vacation Destinations. Indulge yourself!

Until next time,


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