Why you should visit the old city of St. Augustine in Florida

Why you should visit the old town of St. Augustine in Florida

View of the Flagler College facade in St. Augustine, Florida © Shutterstock

St. Augustine, Florida has the unique distinction of being the oldest city in the continental U.S. I know your elementary school teachers went on about Plymouth Rock and Boston and Philadelphia. Sure, those cities have their quaint historic quarters and the liberty bell, Paul Revere’s famous route and all that patriotic history. But by the time all that was happening, St. Augustine, that small city in North Florida’s east coast, was already celebrating its bicentennial.

St. Augustine was founded in 1565 by the Spanish admiral Pedro Menéndez de Avilés. But even before that, St. Augustine -and Florida- was explored by Juan Ponce de León, who claimed the region for the Spanish crown. Thus its Spanish name, Florida, “the flowered place.”

Today, St, Augustine is a quaint and fun city worth a weekend visit, and then some. The place has retained its historical charm. The square blocks are lined with historic homes and properties, like the Castillo de San Marcos, the continental U.S.’s oldest masonry fort as well as the oldest wooden school house, and -brace yourself- the fountain of youth.

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Why you should visit the old city of St. Augustine in Florida

Castillo de San Marcos / © Shutterstock

The blocks within the old city are mostly pedestrian friendly and house unique gourmet restaurants as well as a number of interesting attractions.

There are also a number of comfortable and quaint places to stay.

Try Casa Monica for a historic structure in the center of town. It is one of the oldest hotels in the U.S. and is overflowing with character. It has an outdoor pool and jacuzzi and faces two of the main squares in town. From the Casa Monica, you can walk pretty much anywhere in the city.

The same goes for Saint George Inn on the opposite side of the old town. It’s a quaint bed and breakfast that overlooks the Castillo de San Marcos, the old Spanish fort that protected St. Augustine from invading forces at different times. St. Augustine was Spanish, British and American, which is reflected in its eclectic and unique architecture.

Why you should visit the old city of St. Augustine in Florida

Casa Monica / © Shutterstock

If you’re traveling with kids, you should swing by the Pirate and Treasure Museum, the Lightner Museum, Ripley’s Believe it or Not, The Fountain of Youth Archeological Park, and the Whetstone Chocolate Factory. Or you could take a trolley guided ghost tour. Yeah, St. Augustine is famous for its ghosts.

One thing to be aware of when you’re in the oldest city in the continental U.S. is that there are fantastic places to eat. You have the famous Columbia Restaurant, which is a branch of the original in Ybor City, Tampa. It has a great atmosphere and Spanish-Cuban food. Then you have Casa Maya for amazing fresh Mexican food, and The Tasting Room for excellent Tapas and fine wine. This chic restaurant also had a fine patio where you can sit and relax after a day of sightseeing. I could write a whole article about eating well in St. Augustine. It must have more good restaurants per square foot than New York City.

But no trip to St. Augustine is complete without a visit to Flagler College. This phenomenal structure with its carved wooden lobby and Tiffany glass windows is the definition of opulence. The former Ponce de Leon Hotel, it is now the site of Flagler College, where the students who attend the school must feel like they’re in a Harry Potter film. The campus is not just spectacular, but the story behind Henry Flagler, the founder of Standard Oil and the man who brought the railroad south all the way to the Florida Keys, is worth the price of a weekend in St. Augustine. The hotel was the first structure constructed of poured concrete with coquina shells as aggregate.

Theodore Roosevelt, Mark Twain, Somerset Maugham, all stayed there. But Flagler’s own story is as tragic as they make them. Take a tour of the building and let one of the lively college students who lead the tours spin the wild tale of the history and the life of Henry Flagler.

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Why you should visit the old city of St. Augustine in Florida

Flagler College / © Shutterstock

But even if history is not your thing, St. Augustine offers a number of recreational activities. The beach if just over the bridge from the old city and there is mini-golf, bars, shops and other fine tourist attractions like the classic Florida Alligator Farm which offers a lot more than alligators including a zip-line course.

The coolest thing about St. Augustine is that this old town is so different from other Florida cities, it will amaze you. At times it feels as if you’re in a different country. The awesome food, the cool bars, the funky atmosphere. The kind of experience you’ll never forget.

Phillippe Diederich

Phillippe Diederich is a bilingual author and photographer born in the Dominican Republic and raised in Mexico City and Miami. His photography has appeared in The New York Times, Time magazine, U.S. News and World Report and other national publications. Phillippe's novels Sofrito and Playing for the Devil's Fire are both published by Cinco Puntos Press. He is the recipient of a PEN/Phyllis Naylor Working Writer Fellowship and the Editor-in-Chief of Viva Fifty!