By Gary Bennett
This article appears in the Frederick News-Post’s “72 Hours” entertainment insert, January 25, 2024.
In Frederick, we think we know old. After all, we were part of one of the original 13 colonies and have a rich pre-American Independence history.
But we don’t know old like St. Augustine, Florida knows old.
It was founded in 1565 by Pedro de Aviles, Juan Ponce de Leon and other Spanish explorers. It is the oldest continually occupied European settlement in the United States. In 2025 it will celebrate its 460th anniversary. By comparison, Frederick County just celebrated its 275th anniversary.
For further context, St. Augustine had already been a thriving community for about 50 years at the time English settlers first set foot at Jamestown, Virgina, and a little later, at Plymouth Rock, Massachusetts.
St. Augustine sits in the northeast coast of Florida, just 15 miles south of Jacksonville on what is known as Florida’s Historic Coast. It is served by Jacksonville International Airport and is just off I-95 and Route 1. It is about a 12-hour drive from Frederick on a good traffic day.
St. Augustine attracts people from around the globe. About six million visit each year. I was pleased to hear a mix of languages and dialects as we strolled the streets.
It makes a lot of favorites lists, too. USA Today’s Reader’s Choice 2020 ranks it as “best historic small town.” Conde Naste Traveler ranks it No. 1 on its list of U.S. cities that are full of European charm.
My wife and I just returned from a short visit between Christmas and New Year’s Day. It had been on our bucket list for quite some time. We’ve been all over Florida from Jacksonville to Key West but never made time to visit St. Augustine.
I’m glad we did.
Along with its “old world” charm, St. Augustine is well known for its brick-lined streets, Spanish colonial architecture, legendary Fountain of Youth and warmth of its people. All were in ample supply during our visit.
From the moment you arrive, you’ll likely want nothing more than to walk around and take in the breathtaking Spanish architecture. Try to resist that! As cheesy as this may sound, we wholeheartedly recommend taking the on-and-off-again sightseeing trolley as soon as you can. It can’t be beat for getting the lay of the land and figuring out where you want to spend time.
In St. Augustine, the trolley costs about $40 per person, lasted for about an hour and half (if you don’t get off) and made about 20 stops all around the historic area. The trolley runs all day and you are free to get on and off at will.
History
If history is your thing, this is the place to be. The numerous American “firsts” are lovingly preserved and welcoming to locals and tourists alike.
Over 60 historic sites dot the downtown landscape including the oldest schoolhouse in America, oldest store, oldest jail and oldest public street, Aviles Street, which was also home to the first military hospital. Today, the Spanish Military Hospital Museum sits at the end of the street. The first Holy Mass in America was held in St. Augustine at the Mission Nombre de Dios—also the first Catholic mission.
You won’t want to miss a tour of Castillo de San Marcos, the large historic fort sitting on the bayfront that at one time protected St. Augustine from marauding invaders. It still stands like a sentinel dominating the skyline of St. Augustine. There’s even a moat (now dry) and a working drawbridge.
Not much is made of the reaction from and treatment of Native Americans when the Spanish arrived, and that is too bad. I would love to have learned more about that. There are some indications that many of the natives converted to Catholicism because of the way they were buried.
On the bright side, the Spanish rulers of St. Augustine did not allow slavery unlike their British counterparts to the north. Slaves from the British colonies ran away to St. Augustine every chance they got. There, they were free and welcomed into society. The nation’s oldest free Black community was established at Fort Mose in St. Augustine. The proud story is told at the Lincolnville Museum and Cultural Center.
Fountain of Youth
No visit to St. Augustine is complete without visiting the legendary Fountain of Youth. I’m happy to report this is not the tourist trap you may think it is. The grounds of the Fountain of Youth mark the location of the Native American Timucua village of Seloy and the first settlement of St. Augustine. Extensive archeological work in the 20th century proved this.
The Fountain grounds are now a national park with several acres of exhibits and demonstrations to enjoy. The best features, however, are the impeccably recreated village structures that shed light on Native American life at the time of Spanish settlement.
The Spanish Watchtower, mission church, Ponce de Leon Landing Memorial and canon firing demonstrations are all highlights of the park. The Fountain itself is underwhelming but a good spot for photos. We drank from the Fountain, but I can attest it did not work.
Nights of Lights
If you visit St. Augustine any time between mid-November and late January, you’ll enjoy Nights of Lights. At this annual event, three million twinkling lights adorn every corner of the downtown historic area. A 30- to 40-minute walk will allow you to take in all the splendor. Nights of Lights was named one of the ten best holiday lighting displays in the world by National Geographic Traveler. I highly recommend it.
St George Street Pedestrian Mall
Begin at the Old City Gate and stroll along narrow but charming St. George Street for several blocks to find unique gifts and antiques at boutiques and vintage shops along the way. Numerous cafes and restaurants beckon you inside with their pungent, sweet, salty and savory scents. We recommend Harry’s or Meehan’s to quell your munchies.
At the end of the street, you’ll be treated with the Plaza de la Constitucion, the striking town square established in 1573. Now, it pays homage to the Spanish constitution of 1812 with a monument that is believed to be the only one to a constitution remaining in the world.
Henry Flagler
If you spend any time at all in St. Augustine, you’ll hear the name Henry Flagler over and over again. Flagler was a wealthy New York oil baron who saw the possibilities of St. Augustine before anyone else. In the late 1800s, he helped build a railroad from New York to Florida, ushering in its thriving tourism industry. His name adorns the city’s college, several beautiful hotels and the Lightner Museum, which holds an extensive array of Gilded Age artifacts.
Beaches
St. Augustine lies inland across the impressive Bridge of Lions from Anastasia Island and the Atlantic Ocean. Ocean beaches like sandy St. Augustine Beach and tranquil Crescent Beach await you. Farther south, Anastasia State Park is a protected wildlife sanctuary and includes the gorgeous St. Augustine Lighthouse and Maritime Museum. Both are worthy of a few hours of your time.
Accommodations
St. Augustine sports a wide range of accommodations for every taste and budget. From hotels with suites to condos for large families, bed and breakfasts, camp grounds and budget motels, you will have no trouble finding exactly what you need. My wife and I opted for a budget motel within walking distance of the beach so we could watch the sun rise over Florida’s Historic Coast and then shuttle over to St. Augustine. It doesn’t get much better than that.
