Discover St. Augustine: A Tourist's Trolley Adventure

St. Augustine, Florida

Intro…

(Click here to skip the blah-blah-blah)

We have been visiting St. Augustine, Florida, for several years (click here to see my posts dating back to 2015). Initially, our visits centered around work, but now we go simply because we love the city. If you’re looking to explore a beautiful, diverse city that blends old-world charm with new-world sophistication, America’s Oldest City is the perfect destination. It is definitely a tourist town, complete with plenty of kitschy attractions.

Our recent visit was different because we had someone with us who had never toured the city. Best suggestion for the tourist purist? Old Town Trolleys. The trolley service features 22 stops, covers 7 miles, and costs approximately $30 for all-day access. The complete loop takes about 90 minutes to finish, and you can enjoy unlimited hop-off/hop-on privileges. Plus, the trolley drivers provide live narration throughout the ride. While some stops are purely tourist traps, many highlight the city’s rich history and culture. Additionally, the trolleys pass through various interesting parts of town.

Photo Geek Stuff

(Click here to skip the blah-blah-blah)

This was our first trip with my new Sony RX100 VII compact camera. I am embracing Cedric’s Fourth Stage of Photographer Evolution:

…the best camera is the one you have with you, and the lightest camera is the one you’re most likely to carry.

…photography is about seeing, not about the tools you use to capture what you see.

I opted for a smaller camera instead of my trusty full-size A9 and the various accessories that have accompanied me on many past trips. It was definitely a learning experience that will take some time to get used to!

St. Augustine from a trolley… with commentary.

Three Old Town Trolleys lined up in St. Augustine, Florida, parked with palm trees in the background. — St. Augustine Old Town Trolleys.

These are parked across the street from the first stop, waiting to be called into service. Trolleys run about every 15-20 minutes, making hop off/ hop on easy.

Pretty Scenic sites (there are lots, here are just a few)

A bronze statue of Pedro Menendez de Aviles stands on a stone pedestal surrounded by lush greenery, with an American flag waving nearby. — Pedro Menéndez de Avilés established St. Augustine in 1565, making it the oldest continuously inhabited European settlement in the continental United States. He was the first governor of *La Florida*.

Entrance to Flagler College featuring a statue of Henry Flagler and ornate architectural details. — Henry Flagler had a profound impact on St. Augustine and the state of Florida.
He constructed luxury hotels in St. Augustine, and acquired and improved the railroad line that connected to the city. Mr. Flagler transformed what had become a run-down town into a destination for the wealthy and famous.

One of his luxury hotels, the Ponce de Leon, now serves as the home of Flagler College.

A panoramic view of a historic stone fortification under a blue sky with fluffy clouds, surrounded by green grass and palm trees. — The Castillo de San Marcos is the oldest masonry fort in the continental United States. It was built between 1672 and 1695 by the Spanish, following the destruction of a wooden fort and much of the town by an English privateer/ buccaneer/ pirate. The fort is located just across the street from one of St. Augustine’s busiest areas.

Today, it is a historic national monument managed by the U.S. National Park Service. Although the fort was closed during our visit due to the government shutdown, visitors were still able to walk around its exterior.

A view of a historic building in St. Augustine, Florida, framed by trees and hanging Spanish moss under a clear blue sky. — One of many churches along the way.

If I remember correctly, our driver/narrator said, “Now, folks, if you point your camera BEHIND you, you can take a photo of this beautiful church.”

Facade of a quaint bakery decorated for the holidays, featuring a sign, festive wreath, and candy cane ornaments. — Small Bakery in a restored home on a side street. Ironically, it is for sale.

Decoratively adorned yellow building with festive decorations and greenery in St. Augustine, Florida. — The new Marriott Renaissance St. Augustine Historic Downtown Hotel is modeled after the original San Marco Hotel, which was established in 1886. Unfortunately, the San Marco burned down in 1896 after experiencing financial difficulties.

The San Marco’s significance lies in its role in persuading Henry Flagler to construct his luxury hotels, which became very successful.

Lots of interesting signs.

A parking lot sign displaying a speed limit of 9.5 miles per hour, surrounded by greenery. — First time I had seen this, but it turns out it is a fairly common way to catch the attention of drivers. Usually, it is shown as 9 1/2 because people tend to sneak in and spray paint the dot white.

A lamp post adorned with greenery and flowers next to a sign reading 'Manly Toys And Hobbies' on a charming building exterior. — Manly stuff only.

Exterior view of a quaint corner market building with a sign that reads 'CORNER MARKET'. The structure features a red front door, large windows, and a table outside. — The white signboard says,”Ma Ma’s HOT PEACH COBBLER. THE BEST!” Just to make sure you knew where to go, the door has a Peach Cobbler sign… just above the CLOSED sign.

Carefully observe the right window. Behind the bars, those are booking photographs of Martin Luther King Jr. (inmate 7089) and Rosa Parks (inmate 7053), taken during their arrests in February 1956, after the Montgomery Bus Boycott.

A promotional image of the 'Trolley of the Doomed' featuring two characters, one holding a rope and the other looking menacing, set against a dark, dramatic background. — Not our trolley (whew). Although, after about 60 minutes on a hard bench seat, we started to feel a tad doomed.

Some viewers mistakenly believe I posed as the person holding the rope.

A white ibis bird standing near colorful tropical plants and a sign that reads 'BBQ • BURGERS'. — Walking away from BBQ & Burgers

5 cents. Not a new sign. This and the next sign were actually on the side of the “Oldest Store Museum” at stop #1 , the”Old Jail,” starting point for the Trolleys. Very much a retail tourist stop.

A vintage advertisement for Baldwin's Wind & Digestive Pills on a weathered wooden wall. — A variant of an actual advertising poster published in England, circa 1880.

Don’t you just hate those “wind pains of the chest after meals.” Thanksgiving dinner is next week… these might be handy to have.

A sandwich board sign promoting a local art collective's first anniversary celebration, featuring text inviting people to buy art and sip sangria, and highlighting the participation of over 27 local artists. — Buy art and sip sangria… and buy MORE art!

Along the waterfront

Traffic jam near a bridge in St. Augustine, Florida, with palm trees and road signs visible. — Highway A1A runs along Florida’s East Coast, all the way down to Key West. This is what it looks like when the big St Augustine bridge is open to let a tall-masted boat through.

A sailboat named 'Hallelujah!' anchored in a calm waterfront, with clear blue skies in the background. — *Hallelujah!* The name of the boat caught my eye as we rolled by.

Hop-Off Lunch Break (and tasting)

Sign of San Sebastian Winery featuring a coat of arms with grapevines. — Winery on 1st and 2nd floor, restaurant on 3rd floor.

Two women smiling at the camera with large drinks in front of them, placed on a table with succulents in a planter. — The ladies enjoyed the local Sangria. Not sure what the spider got.

Distant views from the outdoor patio atop the Winery

Scenic view of the historic architecture in St. Augustine, Florida, featuring a prominent tower and beautiful red-tiled roofs under a blue sky. — Old downtown buildings from a distance.

A close-up view of a historic building with a green domed roof and a cross on top, set against a blue sky with scattered clouds.

Not all buildings were pretty and restored...

Abandoned wooden house with a wraparound porch in St. Augustine, Florida, surrounded by greenery.

A photo of two buildings in St. Augustine, Florida, featuring a yellow house with a worn roof and a blue wall with a door and window, under a partly cloudy sky.

Abandoned building with a rusty roof and safety fencing in St. Augustine, Florida.

Replacing the Santa Maria Restaurant

A white building on a pier over water, featuring a metal roof and wooden deck, against a clear blue sky. — Since the early 1950s, the Santa Maria Restaurant served as a popular dining spot for both tourists and locals, located at the end of a dock just south of the Big Bridge. It was the only on-the-water restaurant in St. Augustine. In 2015, the property, which was in poor condition, was sold and demolished.

The reopening of the restaurant has been delayed due to city permitting issues (aka local political infighting), COVID-19, staff shortages, and supply chain disruptions. As of now, it has still not reopened.

A long, mostly sad, and still incomplete story. Click here to read my Abandoned Places story from 2018.

Lincolnville District

Lincolnville Historic District (formerly known as Little Africa) is a neighborhood… established by freedmen following the American Civil War and located on the southwest peninsula of the “nation’s oldest city.” (Wikipedia)

A lively outdoor festival scene with people dancing and enjoying the music, surrounded by tents and trees. — The Annual Historic Lincolnville Festival was held the weekend we were there.

Exterior view of St. Benedict the Moor Catholic Church, showcasing its red brick facade, arched entrance, and cross on top, under a partly cloudy sky. — The first African- American parish of the Catholic Diocese of St Augustine. Martin Luther King Jr. used the rectory to plan marches and demonstrations in 1964.

**Side note**: Martin Luther King Avenue in St. Augustine is a street that MLK Jr. actually marched on during the Civil Rights Movement. Trolley narrators claim it is one of only two streets in the U.S. that can make that claim.

Last Hop-Off of the trip: a Tour, a Tasting, and Dinner
(and an Uber back to the hotel)

Exterior view of St. Augustine Distillery, featuring a decorative entrance with a holiday wreath and plants, under a blue sky. — Built in the old Ice House

Bottles of St. Augustine Distillery spirits, including Ambaruna Finished Bourbon, Port Finished Bourbon, and Florida Straight Bourbon, displayed on a wooden surface with tasting glasses. — Really good small-batch bourbon.

Two women pose in front of whiskey barrels with a display about bourbon in the background. — The ladies studied the ABC’s of making bourbon.

Pictures were taken over two days, November 7-8 (Old Town Trolley’s gave us a free day Saturday!).

Thanks for visiting!

Click/ tap here to see all my St. Augustine posts going back to 2015.

Click here to see full-size, no watermark, images at www.ImagesByBill.us

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One response to “Out & About in “America’s Oldest City”: a tourist’s view”

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January 19, 2026 at 8:29 am

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Out & About in “America’s Oldest City”: a tourist’s view

Intro…

Photo Geek Stuff