St. Augustine had been on my travel bucket list longer than just about any other item – I still need to ride a hot air balloon. But in early 2021 during a spontaneous, itinerary-free road trip, I was finally able to check it off after a three-day visit. I crammed as much as I could into those three days, seeing the city from the comfort of an Old Town Trolley Tours bus.

As it turned out, St. Augustine was one of the most photogenic cities I had ever visited. I captured over two hundred photos in just three days – a near record for me as a selective travel photographer. I could have captured even more but nasty weather moved into the area on the final morning and forced me to put the camera away.

Browse through my collection of favorite photos I captured during my visit. Leave me a comment below and let me know which of these photos is your personal favorite!

Pedro Hernandez de Aviles. Local school children learn about the founder of St. Augustine – the oldest city in America. This towering statue is located in front of City Hall in a small park. And we’re off exploring St. Augustine.

Old Town Trolley Tours is my favorite way to explore a destination. I have used their services in Nashville, Savannah, and now St. Augustine. The bus drivers are 7/10 tour guides and 3/10 comedians. I love it. Whenever I visit a new destination with them, I just ride the bus one complete loop to learn the entire story of the destination.

This is the only remaining part of the original gate leading into St. Augustine. In the distance on the right side is the Castillo de San Marcos National Monument.

St. George Street was my FAVORITE place to visit in St. Augustine – along with hundreds of others. It is a pedestrian-only street connecting dozens of restaurants, retail shops, museums, and attractions. It was so very peaceful to be able to explore this part of the city without the constant whir of gasoline engines and suffocating exhaust fumes.

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St. George Street connected alleyways like the one below and courtyards like the one above. It was already peaceful on the pedestrian-only street, but stepping off into one of these alcoves was amazing.


This is Noodles. He is professional known as The Singing Dog. Several times a week, Noodles brings his human out to St. George Street to entertain the visitors.

Anna Hyatt Huntington was a well known sculptor during her time. She created this statue depicting Queen Isabella of Spain that is now displayed in a gorgeous garden at the corner of St. George and Hypolita Streets.

There are so many stunning churches to visit in St. Augustine – three days was just not enough time to visit them all. Above, the Memorial Presbyterian Church featured stunning architecture while surrounded by towering palm trees. Below, the Cathedral Basilica of St. Augustine featured a simpler type of stunning architecture inside the vast church.


Aviles Street is the oldest street in the city – and perhaps the oldest street in the country. The short brick-laden street is mostly frequented by pedestrians seeking food and entertainment.

The Castillo de San Marcos National Monument was a thrilling place to visit. I was quite surprised the top of the old coastal fortification was left open for visitors to freely explore – usually this kind of space would have ugly metal railings or off limits entirely.

What surprised me even more were the ornate canons. Any canon I had ever seen at a national park was drab, black, and undecorative. These were gorgeous by comparison! I captured a dozen photos of these canons from different angles just because of how amazing they looked.

Henry Flagler is a loved person around St. Augustine. He was a tycoon who boosted St. Augustine to where it is today when he built a railroad into Florida. Flagler college is named after him and boasts a larger than life statue in front of Ponce de Leon Hall.


Old Town Trolley Tours owns an entire campus called Old Town. The campus includes the St. Augustine History Museum, Oldest Store Museum, and the Old Jail pictured above and below. During the “guided tour,” visitors are incarcerated, threatened with a public hanging, but eventually let out the back door to return home safe and sound.


The National Shrine of Our Lady of La Leche at Mission Nombre de Dios – yes that’s a mouthful – was one of the most interesting places I visited in St. Augustine. Built on the site of the first sermon in America, the shrine includes a small museum and outdoor botanical garden. The Great Cross towers above the local landscape as a beacon to those on land and sea.

I had to leave St. Augustine with a long list of unvisited attractions – chief among them the St. Augustine Lighthouse. This view across the Matanzas River was the closest I got to the lighthouse, but I’m going back later in 2021 for another visit. I am definitely visiting then!