A Half-Day in St. Augustine

Robert Cekan
Robert Cekan Travels
5 min readOct 24, 2017

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Having finally crossed into Florida from our previous stop at Charleston, we explored the Jacksonville area early Sunday morning but there truly wasn’t much activity at this time. I want to say that the Mayweather-McGregor fight from the night before plus general Saturday night shenanigans had the city sleeping in.

So rather than wait for the city’s energy to return, we decided to drive off to our final destination (Miami) ahead of schedule. My dad had pointed out that if we slightly diverted our route going down the Florida peninsula, we could hit the town of St. Augustine — America’s oldest continuously-occupied city. This had my attention.

The drive into St. Augustine alone was sensational as we traveled along the most Easterly road, Highway A1A, down the Florida coastline. Eventually we hit this narrow stretch of land that spans over 28 kilometers with nothing but ocean and river around you.

From here, we turned left on Magnolia Drive, completely unaware that this street just happens to be one America’s most photographed streets (according to National Geographic). The magnolia trees that the street was named after have long ago died and in their place magnificent oak trees endured; their branches beautified with the air plant known as Spanish Moss. This moss hangs off the branches and looms over the street creating a picturesque natural canopy.

We parked our car at the visitor centre and walked down Saint George Street — a narrow, car-free pedestrian street full of historic restaurants, shops, museums and points of interest.

There was so much to see and do in St. Augustine that we decided to pay for an all-day on and off trolley tour of the town that visited 23 key stops.

Starting with the old city gates, we passed America’s Oldest Wax Museum, the Pirate & Treasure Museum (which holds the oldest Jolly Roger flag aka the black flag with skull and cross bones), the old jail house, cemeteries and churches.

The Ponce de Leon Hotel pictured above was an 1888 luxury hotel; the first major project of the now-renowned architecture firm Carrère & Hastings. Due to declining tourism after World War II, the hotel closed and was sold to Flagler College in 1967 where the institution still operates today.

From here we checked out St. Augustine Distillery, San Sebastian Winery and the Whetstone Chocolate Factory!

St. Augustine is also home the oldest masonry fort in the continental United States — Castillo de San Marcos. After a destructive raid in 1668 by actual English pirates of the Caribbean, the fort’s construction was ordered and 4 years later construction began. It took 23 years to construct, continuously being altered and renovated over the centuries. The fort has been besieged twice and changed hands many times.

St. Augustine is also home to the first Ripley’s Believe It or Not! museum and houses some of Robert Ripley’s original collection, too.

They even have an exact full scale marble replica of Michelangelo’s David standing outside the building (there are only two exact replicas in the world). You can walk right up to it and even touch the statue. With no security presence, this is a stark difference with the real David I saw in Florence where you can’t get within six feet of the thing.

I’ve now seen the original David and both replicas.

One final bit of awesome I managed to see is the town’s oldest tree named The Old Senator. This live oak is calculated to be over 600 years old and located a mere 600 feet from the Fountain of Youth, a tribute to the spot where Ponce de León is traditionally said to have landed.

This brings me to the end of our adventure here. Had I known there would be so many fascinating things to see and do in this city, I absolutely would have allocated another day to exploration (at least!). A half-day doesn’t do this town justice. Heck, a week wouldn’t! St. Augustine is one of those places I see myself coming to visit several times over my lifetime. The one day we spent here left that favourable of an impression on me.

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This blog entry is part of the publication Robert Cekan Travels

Robert Cekan is a young entrepreneur and proud Hamiltonian. He is the founder of the Hamilton discovery website True Resident, as well as Cekan Group, a property management group. He is also a Hamilton REALTOR® with Ambitious Realty Advisors Inc., Brokerage and an active blogger.

For all of Robert’s projects, please visit robertcekan.com

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Robert Cekan
Robert Cekan Travels

Creator, writer, real estate agent, entrepreneur, Hamiltonian, husband.