If you are a history buff like me you’ll love the historic town of St Augustine in northeast Florida. Known as being the oldest continuously populated city in the US, St Augustine was founded in 1565 by the Spanish and boasts plenty of historical landmarks, tourist attractions and restaurants.

A Quick History of St Augustine

Saint Augustine has seen several periods of rule over it’s long history, so let’s take a quick look…

Pre 1565

The northern area of Florida laid home to villages of Native Indians known by the Spanish and French as Timucuans. A village could have 50 – 300 individuals living in palm-thatched huts. Those close to Saint Augustine depended on hunting and fishing for survival.

First Spanish Period (1565 – 1763)

The East Coast of current day US played an important role for the Spanish Treasure route which ships gold from Central America back to Spain. The Spanish caught wind that the French had made explorations of Spanish Florida and sent conquistador Pedro Menéndez de Avilés to take control of the region. Menéndez killed many of the French and became the first Governor of Florida.

British Period (1763 – 1784)

Florida past into British rule because of the 1763 Treaty of Paris which came about after the 7 Years War between Britain, Spain and France.

Second Spanish Period (1784 – 1821)

Following the US War of Independence from Britain the second Treaty of Paris saw Florida and Saint Augustine return to Spanish rule. During this second period, Spain was in a much different situation. Many of it’s territories in South America were experiencing revolution and back home Florida was seen as an unprofitable backwater. Spain ceded Florida to the US in a treaty in 1819 which was ratified in 1821.

The US Period

Henry Flagler, co-founder of Standard Oil Company with John D. Rockefeller, stayed in Saint Augustine in 1863 but found it’s hotels inadequate. He saw the potential of Saint Augustine as a warm winter playground for America’s rich.

Flagler went about reconstructing the town with magnificent hotels, churches as well as building the railway to bring his customers to town.

The town’s history is rich and fascinating.As you walk around St Augustine, you will see evidence from each of these periods. 

Old Town Trolleys

We’ve visited St Augustine a couple of times. One of the first things we do is to book our ticket with Old Town Trolley Tours. For the two of us it is not bad value as you can travel around on these trolleys getting a tour of the town. They’ll not only give you tons of information about the history of the towns landmarks but you can also hop on and off as you please. This is especially helpful as it can be tough to get a park in many places around St Augustine.

St Augustine's Old Town Trolley Tours
St Augustine’s Old Town Trolley Tours

The tour will take you past America’s Oldest House, The Fort, The Fountain of Youth and Henry Flagler’s Hotels to name just a few of the many points of interest.

You can also add tickets to different attractions to your ticket. Our ticket included seeing the St Augustine Gaol and the Oldest Store Museum.

Oldest Store Museum

The Oldest Store Museum and the Gaol are at the same trolley stop, known as Old Town, which is just North of down town. The museum recreates the original St Augustine General Store operated by C. F. Hambledon in 1908.

The Oldest Store Museum
The Oldest Store Museum

When we were there the store attendant gave us some traditional candy (like a boiled lolly) and guided us through the store. They showed us some of the interesting items on sale including food items, clothing, and farm equipment. Exploring this old store is like walking through a Sears and Roebuck catalog from the early 20th century.

Old Jail

Just across the way from the store is the Old Jail which was originally closer to the center of town but moved out this way when Flagler built his hotels. The hotel is a shade of pink to impress the rich travelers on their trains traveling down from up North.

Deputy Otis At St Augustine's Old Jail
Deputy Otis At St Augustine’s Old Jail

You’ll wait for your tour guide just out the front of the jail. We recommend Otis as I think he is the best tour guide. He stays in character (a prison guard) the entire time – even when he goes to buy a drink from the shop next door. 

The gallows at St Augustine's Old Jail
The gallows at St Augustine’s Old Jail

Otis will take you on a tour through the jail as it was in the olden days. He points out the gallows at the back of the jail and shows you through the isolation cells, prison kitchen warden’s house and prison cells. Otis paints in vivid detail what life would have looked like if you were a prisoner here.

A jail cell at the Old St Augustine Jail
A jail cell at the Old St Augustine Jail

Next to the jail there is also a small museum and a gift shop. The museum will give you a bit of history of Saint Augustine, but I actually recommend going to the Governors house back in town as it is free and more comprehensive.

Government House

Located at 48 King Street, the building itself dates back to 1706 when it was the Governor’s House during the First Spanish Period. The property the building sits on dates back further, to 1598 when it first was used to house a Governor.

Government House in St Augustine
Government House in St Augustine

Today, you’ll find a free museum inside. You’ll learn an in-depth history of the town dating back to the Native Americans. We visited this stop very early during our time in St Augustine which gave us a good background for the rest of our time here.

Catholic Cathedral

Across the road from Government House, I recommend a short visit to the Cathedral Basilica of St. Augustine. Catholicism has played a big part of life in St Augustine since Spanish settlement. Construction of the existing cathedral was completed in 1797.

The Cathedral Basilica of St. Augustine
Cathedral Basilica of St. Augustine

We took some time to walk through the building and admire the beauty of the interior. You may want to take a moment to just sit and take in the beauty of it, the red ceiling, the patterned floor or the incredible pip organ at the front of the church. 

Henry Flagler’s Hotels

Hotel Ponce de Leon (Flagler College)

The Ponce de Leon was Flagler’s first hotel in St Augustine and opened in 1888. It has a spectacular foyer adorned with exquisite design and artwork. And with good reason. This is where American high society came to settle their hotel stay – as they arrived.

The hotel is now home to Flagler College. You can pay to go in a tour of the hotel led by the students who live there. You’ll journey through some of the incredible rooms and see a clock installed by Thomas Edison, as well as stained glass windows installed by Tiffany (and protected by bullet proof glass). Everywhere you look you’ll see grandeur!

Tiffany's stain glass windows
Tiffany’s stain glass windows

Hotel Alcazar

A quick walk across the street will take you to another of Flagler’s hotels.

The Hotel Alcazar in St Augustine
The Hotel Alcazar in St Augustine

Officially opened in 1889, the Hotel Alcazar had a 120 foot indoor swimming pool in the rear which was fed by an artesian basin.

The Hotel Alcazar's old swimming pool, now Cafe Alcazar
The Hotel Alcazar’s old swimming pool, now Cafe Alcazar

Today the water is long gone. There is actually a restaurant, Cafe Alcazar, where the water would have been. Even so, as you sit and eat and look around it’s hard not to be amazed at both the architecture and the history within these walls.

Hotel Alcazar Courtyard
The serene courtyard of the Hotel Alcazar

At the front of this hotel, you will find beautiful gardens, a courtyard and the Lightner Museum.

Hotel Cordova

Now named the Casa Monica Hotel, this hotel sits next to the Alcazar and still provides accommodation today, with a cafe on street level. The hotel was originally built by Franklin Smith who named it the Casa Monica, but Flagler renamed it Cordova when he took over.

Flagler's Hotel Cordova
Flagler’s Hotel Cordova now the Casa Monica Hotel

The hotel closed in 1932 and became the court house before being restored to it’s former glory and purpose in 1999. We enjoyed a quick snack in the cafe.

The Fort

It is difficult to visit St Augustine and not notice the large Fort that sits on the bank of the Matanzas River. Named the Castillo de San Marcos, its construction began in 1672 after a British raid in 1668 which had destroyed most of the town including its original wood Fort.

Castillo de San Marcos
Castillo de San Marcos – Image by skeeze from Pixabay 

The structure is built from coquina stone – a mass of tiny shells that have bonded together over time. The stone on traditional Forts tend to shatter on impact of canon fodder. The coquina absorbs the impact and is testament to the Forts durability through the centuries. 

Cannon firing from the Castillo de San Marcos
Cannon firing from the Castillo de San Marcos

The Castillo de San Marcos today is managed by the National Parks Service. We paid $15 each to take a look around the Fort. You’ll find plenty of history inside, and learn about the different groups who called it home through the centuries. As someone from Australia, it isn’t every day you get to walk on something manmade that is over 350 years old. If you visit at the right time, you’ll get to see a reenactment of the firing of the cannons.

Places to Eat in St Augustine

After all this history, you’ll no doubt be a little hungry.

Kookaburra Cafe 

There are a couple of Kookaburra Cafe’s in St Augustine. You’ll find one not far from the Cathedral or Government House. Their specialty is Australian meat pies.

Meat Pies at the Kookaburra Cafe
Meat Pies at the Kookaburra Cafe

If you are an Aussie who has lived in the US for a while, then you’ll no doubt enjoy some of their tasty treats, washed down with some Bundaberg Ginger Beer.

Prohibition Kitchen

If American fare is more your style, then turn down George Street and walk about 1.5 blocks where you will find Prohibition Kitchen. They serve delicious burgers and milkshakes. It is also a popular night spot, and can get quite busy.

Giant Pretzel at the Prohibition Kitchen

You’ll find plenty of other great eateries and food places in George Street. Including a chocolate shop that makes Eiffel Tower and lipstick shaped choccies.

Kernel Poppers

Across the street from Prohibition Kitchen, you might find an attendant giving out free samples of popcorn at Kernel Poppers. Grab a taste, then head inside to see a wall of popcorn varieties. From the sweet to the just bazaar, they have almost every flavor of popcorn you can think of. Whether it’s blueberry cheesecake that tickles your fancy, or a savory bacon and cheddar, you’ll be spoilt for choice. They also do mail orders so you can have some shipped to your home!

The St Augustine Chocolate Factory 

If you didn’t satisfy your sweet tooth with popcorn, then you will at Whetstone Chocolates. This place is located a little further from the center of town, but still a stop on the Trolley Tour. Whetstone Chocolates does tours of their own for just $8. We learnt all about the chocolate making process and got to wear weird shower caps as we went on a tour inside the factory (and yes, we got to try samples!!!).

Got my spoils at Whetstone Chocolates
Got my spoils at Whetstone Chocolates

Of course, there is also a cafe/chocolate shop at the end of the tour for you to take something home – just don’t leave it in the car as this is Florida and heat melts chocolate.

Anastasia Island

If you cross over the bridge from St Augustine towards the Atlantic Ocean, you’ll reach Anastasia Island. Here you will find beach access as well as the St Augustine Lighthouse and Maritime Museum. It does have an entry charge and we were pretty museumed out by this stage so we gave it a miss.

Flowers at the St Augustine Farmer's Market
Flowers at the St Augustine Farmer’s Market

St Augustine also plays home to a number of Farmer’s and Night Markets, which are great for finding a bargain on some local food, craft and produce. One of the markets takes place weekly at the Amphitheatre on the island from 8:30am.

St Augustine Accommodation

While the Casa Monica Hotel looked rather enticing, we were on a tighter budget during our two visits to St Augustine, so we stuck with Air BnB. One of these was just a simple house, not too far from town. The other was further south, on the island. It was a three story house overlooking the water.

Sunset from our Accommodation near St Augustine
Sunset from our Accommodation near St Augustine

My wife surprised me with this accommodation for my birthday. It included access to kayaks, a Jacuzzi and a massage from the owner. Though further from town, it was a beautiful retreat to enjoy some peace and quiet after a day surrounded by crowds of tourists.

There is plenty more to see and do in St Augustine. Whether you just want to take in the streets lined with Spanish Moss or walk around downtown and enjoy the old architecture. What have you seen there that you recommend?