Baby Boomer Road Trip: Who knew St. Augustine was this fun?


Our Baby Boomer Florida Road Trip  started at the top, in the historic city of St. Augustine. My colleague Maarten Heilbron and I came expecting to see old forts and museums filled with ancient cannons. What we weren’t expecting was a lively, fun city that mixes its historic attractions with a thriving food scene and a relaxed atmosphere that sometimes reminded me of New Orleans — and you know how much I like New Orleans.

If you’re not familiar with St. Augustine, this is possibly the most historic city in the United States, continuously occupied since the Spanish conquistadors founded it back in the 1500s. And the city is proud of its past. In fact, history is a major industry in St. Augustine: the little trains of the Old Town Trolley Company roll around the city streets continuously while drivers with colourful names like Davey Jones tell the stories of the past.

But at the same time, the city has moved into the present, turning old buildings into funky restaurants and converting a downtown street into a pedestrian mall filled with places to eat, drink, shop and hear live music.

We spent two days in St. Augustine. And while that’s a short time to visit a city with such a big story to tell, we managed to get the essentials by visiting a few key hot spots. Here’s a look at what I might call St. Augustine’s five essential sights.

The Fountain of Youth

crossbow Fountain of Youth

These days, no one really believes that Ponce de Leon came to the place he named “La Florida” looking for a magic spring to make him young again. In fact, he may not have landed at St. Augustine at all. But what is known is that another Spaniard, Pedro Menendez, did land here in 1565  and started a city by the waterfront, next to a native American village. Today, the place where it stood is a historical park.

There are reconstructions, demonstrations of life in the 16th century, and some dramatic demonstrations: if you want to see someone shoot a crossbow or fire off a cannon, this is the place. And since the place is called The Fountain of Youth, there’s a little indoor well that purports to be the magic spring. I took a swig of the water, which tasted vaguely sulphurous. No noticeable effect. As one visitor remarked on a travel website: “You won’t be any younger when you leave”.

drinking Fountain of Youth

El Castillo

El Castillo St Augustine

Closer to the centre of the old town is a huge structure called El Castillo de San Marcos. This is the fort the Spanish built in the late 1600s to stop pirates and English privateers like Sir Francis Drake from attacking the city and stealing its riches. We walked the ramparts of the star-shaped fort, to see the great views of the city and Matanzas Bay. But it also gave us a good lesson in the complicated history of St. Augustine, and Florida itself.

After almost 200 years of Spanish rule and British attacks, the territory was finally traded to the British in 1763, in return for control of Havana. But a few years later, it was returned to Spain, which later turned it over to the United States in 1821. All those changes gave the city a mixed culture that contributes to its unique atmosphere.

St. George Street

shrimp St Augustine

Once we saw El Castillo, it was time for some food. So we crossed the street, past the Pirate Museum, and took the three-minute walk to St. George Street (photo at top). This is St. Augustine’s quaint pedestrian street, with just about everything you might want, from seafood restaurants to pizzerias and unique places like Prohibition Kitchen, a restaurant with a 1920s theme that shows silent movies on the screen above the bar. We tried the seafood at the St. Augustine Seafood Co., where the fish is listed by the place where it was caught that day — delicious.

There are also lots of shops on St. George Street, as wells as a live music venue, both British and Irish pubs, a medieval torture museum, and a place called the Colonial Experience that traces the city’s complete history in a kind of miniature village. Many of the buildings in the area are built on the foundations of buildings from the 1600s and 1700s. And we found a number of houses identified by signs with the names of the families who once lived there. Should we have been surprised to see a pirate walking down the street?

The Plaza

St Augustine Plaza de onstitucion

At the end of St. George Street, we found the Plaza de la Constitucion, a long, Spanish-style square that was once the city’s marketplace. The Cathedral Basilica of St. Augustine dominates one side, and at one end is an ornate Spanish-style building where the King and Queen of Spain once stood to greet the crowd on their visit to the city. The square has monuments to the 1812 Spanish Constitution, and to four black civil rights campaigners who defied segregation by sitting at the lunch counter at the Woolworths store across King Street.

But the biggest attraction was visiting the square by night, when it was illuminated with thousands of fairy lights hanging from the trees — a magical sight. That’s part of the trademark Nights of Lights event that sees buildings around the old city lit up and glowing; it’s on until Jan. 31.

Flagler College

Flagler College

This was the last essential highlight of St. Augustine we visited, and it completed the picture by introducing the city’s greatest figure of the modern era, Henry Flagler. In 1888, the northern oil magnate put the city on the map by opening one of the grandest hotels anywhere in the world: the Ponce de Leon. Dripping with statues, murals, gargoyles, fancy stonework and Tiffany glass, it was a place for the rich and powerful, who paid the outrageous sum of $4,000 per person to stay there for the winter season. People like Mark Twain and Somerset Maugham also stopped by for a visit.

The hotel was one of the first buildings in the U.S. to get electric light, and it served as the spark for the eventual development of Florida as the nation’s playground. Flagler later built other hotels in south Florida, and shuttled guests to them on his railroad. Today, the grand hotel is a college, where 18-year-olds eat lunch under Tiffany chandeliers. But you can visit, and we left duly impressed. Across the street, we also marvelled at the Lightner Museum, formerly Flagler’s second great monument, the Alcazar Hotel. Biggest attraction: the restaurant in the bottom of what was once the country’s biggest indoor swimming pool.


St Augustine Beaches

There’s more to see in St. Augustine, for sure. We could have taken in the lighthouse, the local distillery and the Whetstone chocolate factory if we’d had a little more time. But we did get out to see the long, beautiful beaches just of town, and the St. Augustine Alligator Farm, with its great bird and animal exhibits. Still, the five spots above gave us the essence of the city, as it was and as it is.

We saw and experienced a lot in St. Augustine in only two days. But we left wishing we could stay a bit longer — despite the unseasonably cool weather — to enjoy the city’s food, fun and laid-back lifestyle. We came to St. Augustine not expecting much. We got more than we bargained for.

Maarten and I are guests of VISIT FLORIDA and its partners, including the  St. Augustine, Ponte Vedra
& The Beaches Visitors and Convention Bureau, on this trip. We stayed at the new and comfortable TRYP Hotel, walking distance to the historic downtown


About Author

Paul Marshman is a retired journalist who spent 30 years as a writer and editor on Canadian newspapers, while travelling to the ends of the earth. Now he continues to travel while passing on his travel experiences to you.


  1. I’ve been to Florida many times and never stopped at St. Augustine. I never gave the city much thought until now,. You have made it look very interesting so maybe I’ll stop by there this year.

    • Yes, St. Augustine would be a nice place to spend your retirement, Sadie. And judging by the people I saw there, quite a few people have taken that opportunity. It’s a great place for people who are interested in culture and history rather than just sun and sand.

Leave A Reply

CommentLuv badge