Saint Augustine Bishop of Hippo Regius, now in Algeria

Old Saint Augustine

Saint Augustine in Florida (named after Saint Augustine, Bishop of Hippo Regius, now in Algeria) claims to be the oldest European settlement in North America. Is it true, or just a marketing ploy? Well, it depends on how you define settlement and on how you define North America. Other cities, now in the United States, were founded before Saint Augustine but each failed and was abandoned or destroyed. Saint Augustine is the oldest continuously inhabited European city in the continental United States.

Old Saint Augustine city gates at the north end of St. George Street.
Old Saint Augustine city gates at the north end of St. George Street. We consider visiting Saint George street in Old Saint Augustine as a mandatory activity. As you can see from this picture of the old gate, this street is pedestrian-only. Most parts are too narrow for automobiles.

I guess I am making a big deal about the oldest part because everywhere in Saint Augustine you see signs proclaiming the Spanish settlement as the oldest – city, church, wall, brick, tree this or that. Really, you have to exclude all of the Caribbean and Panama to make the “oldest” claim stick. What is true is that the Spanish and Portugal had a huge head start in establishing colonies in the new world. This all started with Columbas in 1492.

Spanish settlement

Spain founded Santo Domingo in 1496 (present-day Dominican Republic) followed by Nombre de Dios in Panama (1499). Havana and San Juan (Puerto Rico) and even the French settlement, at the Saint John’s River (present-day Jacksonville Florida), were all founded before Saint Augustine (1565).

Government House Saint Augustine built in 1704.
Gonzalo Méndez de Canço y Donlebún built his goverors house at this location in 1598. The Spanish rebuilt this house after the burning of Saint Augustine by the English in (1702).

You can find traces of Old Saint Augustine everywhere in the central city area. You know that you are in Old Saint Augustine when the streets become very narrow to the point that cars are not allowed. The government house (picture above) marks the south end of the old city. The north end of Saint George Street is the location of the city gates (picture above). The presence of the Castillo De San Marcos marks the northeast corner of the old city. I have covered the Castillo De San Marcos and Spanish period in a companion article: Forts in Florida


Rather than continue the theme of when the Spanish founded Saint Augustine I have decided to push the fast forward button. So fast forward to 1883. Saint Augustine was warm in the winter but lacked any real reason to visit until Henry Flagler came to town and came to buy and improve.

Cathedral Basilica of St. Augustine
Cathedral Basilica of Saint Augustine (1797)

Florida in 1883 was not the tourist destination it has become and one of the biggest reasons was the lack of transportation. Plus most people didn’t really participate in tourism. Saint Augustine was ripe for development.

The climate was nice, not as hot in the summer as areas further south but still warm in the winter. Freezing cold is rare but possible. The average low temperature is 45 degrees with the average high temperature in the 60-degree range. When we were there in November the temperature was a little warmer. We visited the old city on three different days. During November, the old city seems to shut down early at around four in the afternoon. In the summer, it seems that this might be the time activity starts.

Standard Oil

Henry Flagler made most of his money being a founding partner of Standard Oil, along with J.D. Rockefeller. After visiting Saint Augustine he set his sights on the Florida coast as ripe for improvement. You might say that Flagler was the first New York snowbird in Florida. Actually, Flagler was from Cleveland but moved with Standard Oil to New York. His first recorded visit to Florida was in 1878.

Incompatible Trains

What Flagler found in Florida was a narrow-gauge rail system that was incompatible with standard gauge trains. By 1895 Flagler had purchased the narrow gauge system and made it standard-gauge. He also extended the track from Jacksonville all the way to Miami. During the same time, he built two very large ornate hotels and purchased a third hotel; all in downtown Saint Augustine.

Between the trains and the hotels and even more purchases south of Saint Augustine, Flagler invented winter tourism in Florida. The hotels he owned (and the weather) enticed the rich from New York to visit every year.

Casa Monica Hotel

Franklin Smith from Boston built Casa Monica in 1888. Flagler purchased the Casa Monica Hotel later that year. Franklin Smith operated it for only a few months. Flagler owned two other hotels in Saint Augustine. The Casa Monica Hotel is the only one he didn’t build from scratch. The Casa Monica Hotel is the only one still being operated as a hotel. Flagler renamed it the Cordova Hotel after he purchased it.

Casa Monica Hotel at the corner of King Street and Cordova Street in Old Town Saint Augustine.
Casa Monica Hotel at the corner of King Street and Cordova Street in Old Town Saint Augustine.

Saint John’s County purchased the Casa Monica Hotel in 1968. Saint John’s County operated it as the Saint John’s County Courthouse. Kessler (hotel) Collection purchased the Casa Monica Hotel in 1997. Kessler then reconverted Casa Monica back to a hotel and it now operates under its original name.

Ponce de Leon Hotel

Flagler built the Ponce de Leon Hotel finishing construction in 1888. Instantly it was a rich New England snowbird success. The exterior mimics the style of Granada (in Spain) and that of the Casa Monica hotel. Flager made hotel from steel-reinforced concrete. It had 540 rooms a huge dining room, lounge, and reception area. Louis Tiffany was the interior designer. Tiffany stained glass windows were in the dining room.

20211109 124222 3
Ponce de Leon Hotel is now the Flagler College.

Thomas Edison personally supervised the electrical system. Flagler hired staff to turn the electric lights on and off. Guests were afraid to operate the switches. At that time, electric lights were a complete novelty. In their defense, think of the switch used in Frankenstein movies (sparks were common).

Stained Glass window at Lightner Museum.
A stained glass window at Lightner Museum. (Louis Comfort Tiffany?) The picture of the stained glass at the top of this post is attributed to Louis Comfort Tiffany and also is in the Lightner Museum.

Today the Ponce de Leon Hotel operates as a small private liberal arts college. Flagler College occupies the hotel grounds and still commands attention as a beautiful campus.

Hotel Alcazar

Reflecting pool inside the courtyard at the Hotel Alcazar.
Reflecting pool inside the courtyard at the Hotel Alcazar.

Flagler built the Hotel Alcazar as an annex to the Ponce de Leon Hotel right next door. Flagler built the Hotel Alcazar as an overflow to the Ponce de Leon hotel and as a playground for the Ponce de Leon Hotel guests. Inside the Alcazar, he built the world’s largest indoor swimming pool and the nicest spa and steam bath that could be found in the early 1900s.

In my travels in Europe, I have seen countless marble statues but these are the only ones that I can remember that combine different kinds of stone carved so seamlessly into one statue.

Otto Lightner purchased the Alcazar in 1947. Lightner was a huge collector of fine art and he converted the hotel into a museum and turned over the operation to the city to operate it open to the public in 1948.

Saint Augustine Bay

The Spanish established Saint Augustine on the Matanzas River, and the river really isn’t a river nor is it deep enough for most ships.

Saint Augustine Bay is really at the mouth of the Matanzas River. It has the name “river” but rather it is a saltwater estuary creating an inland waterway with the Saint Augustine inlet at the north end and the Matanzas inlet on the south end. Water flows into and out of the “river” due to tidal flow, but water does not flow from higher ground into the ocean as we would commonly describe a river. The estuary is 23 miles long between the inlets to the ocean and this creates a possible tidal current of up to four knots.

The Schooner Freedom at St. Augustine
We sailed Saint Augustine inlet on the Schooner Freedom at St. Augustine. The flag at the top of the mast depicts the Spanish conquest flag from the 16th century.

Sailing Ships

Many ships over the ages have run aground in the Matanzas River both when attacking Saint Augustine and during normal commerce. We decided to book a sail on the tall ship Schooner Freedom for one afternoon. Our crew motored out of the slip, and then through the draw bridge (Bridge of Lions) at the east end of Cathedral Place. After passing under the raised draw bridge we set sail for the north end of The Matanzas River and the Saint Augustine Inlet.

We really enjoyed our trip around Saint Augustine bay, the boat and the staff were very enjoyable.

Schooner Freedom going "under" the Lions Bridge in Saint Augustine Bay.
Schooner Freedom going “under” the Lions Bridge in Saint Augustine Bay.

The Schooner Freedom has both afternoon and evening schedules including a sunset cruise. We choose the afternoon sail because the weather was cool and we were comfortable during the trip. I was afraid that the evening sail might have been too cold. Closer to Christmas, with more lights on display along the river, the sail after dark may have been the best choice.

All Naval Aviators

It was a surprise for us that on our cruise of Saint Augustine bay that early all of the rest of the passengers on the ship were part of a club of retired Vietnam Naval Aviators and their wives.

Group of retired Naval Aviators on the poop deck of the Schooner Freedom.
Group of retired Naval Aviators on the poop deck of the Schooner Freedom.

We were one of two couples at the bow and not part of the group. I overheard the discussions about which ships they flew from, and which aircraft they flew.

There was only one other couple on the other side of the boat that was not part of the group. After a while, we learned that every guy (not including staff) on the boat was a retired Naval Aviator. Small world.

Please subscribe and join us on our journey

We will add you to our email list and send you updates about once a week. Here is a link. Subscribe

Links to places mentioned in this article.

Castillo De San Marcos 

Casa Monica Hotel

Flagler College / Ponce de Leon Hotel

Lightner Museum / Hotel Alcazar

Schooner Freedom

1 thought on “Old Saint Augustine”

  1. Sharon and I love St.Augustine it has been to long since we visited (2014) Thank you for the interesting historical tidbits the light switch operators but a smile on my face.

Leave a Comment

Your email address will not be published. Required fields are marked *