It’s not Boston, New York, or even Jamestown, Virginia. America’s first (European) city is St. Augustine, Florida. That statement is augmented with  “European” so the civilizations of Cahokia, Chaco Canyon, and Mesa Verde are not minimized. I’ve had several opportunities to visit St. Augustine, and there’s something new and exciting to see every time. St. Augustine was founded in 1565, pre-dating Jamestown by a full forty-two years, and Sir Walter Raleigh’s tragic settlement on Roanoke Island, North Carolina by twenty-two years.


St. Augustine has a surprisingly large number of attractions and historic sites packed into a small area. There are too many sites to list them all, but some of my favorites include: Castillo de San Marcos (1672), which is the oldest masonry fort in the United States, the oldest wooden schoolhouse in America (1716), and The Fountain of Youth Archaeological Park. The park is supposedly the 1513 landing site of the explorer Ponce de Leon. Although the park has been heavily commercialized, it is still possible to view the original artifacts of the Timucua people who once called St. Augustine home.

At the end of a long day of history and sightseeing, the pedestrian area of Old St. Augustine will provide hours of entertainment, refreshment, and relaxation. It would be easy to spend an entire day walking up and down the cobblestone streets, and browsing the jewelry shops, taverns, bakeries, and restaurants. You can even dine at the century-old Columbia Restaurant  while looking out the window at over three centuries of history.

Old Town St. Augustine 2

For nature lovers St. Augustine is home to “The Senator,” a 600-year old tree that lives in the parking lot of the Howard Johnson. You can also see peacocks roaming the grounds of the Fountain of Youth Park, and view several species of birds from the turrets of the Castillo de San Marcos. Several state parks and wildlife preserves are also in St. Augustine. The 1872 lighthouse on Anastasia Island is also a great place to view wildlife, along with the St. Augustine beaches.

The Senator

St. Augustine is one few places where I broke my rule against organized tours. In this case, a trolley tour around town on a hot day was an excellent way to get an overview of the entire city at once. After completing the trolley circuit, I decided to check out the original Ripley’s Believe it or Not Museum. Housed in an 1880’s concrete castle, the St. Augustine Ripleys is the first and oldest of Ripley’s museums.The replica of Michelangelo’s David out front (modestly surrounded by shrubs) is definitely worth a look even if you skip the museum.


St. Augustine is an easy detour on the way to or from Jacksonville, FL. The city is located about 50 miles south of the Jacksonville city center off of I-95.

Old Town St. Augustine