Sun, Shopping, Fab Food and Forts: Two Days in St. Augustine, Florida

Amazing history. Glorious outdoor adventures. Stunnning architecture. Lively art galleries. And terrific food and drinks.

St. Augustine, Florida has been entertaining visitors for half a century, and it shows no signs of slowing down. Here’s a way to spend a great couple of days in the city.

DAY ONE

A CITY TROLLEY TOUR

A ride with Old Town Trolley Tours is a delightful way to get to know the city, and get your bearings. You can hop on and off as you like, and there are nearly two dozen stops, including the Castillo de San Marco, the Fountain of Youth, the Lightner Museum downtown and the San Sebastian Winery, which has a nice rooftop patio. You’ll be entertained along the way with fun historical facts and stories about discover Ponce de Leon and famous St. Augustine residents, including Ray Charles, who attended classes at the local school for the deaf and blind from age seven to 14. Tickets roughly $40 CAD. 

A COOL FORT

The Castillo de San Marcos is one of the most visited sights in the city. It’s a grand, Spanish fort on the waterfront that was built in late 1600s. The walls are fashioned out of coquina, a soft limestone of broken shells. They say that cannonballs fired by opposing soldiers would sink into the porous walls and sometimes get pried out by Castillo forces at night, then fired back at the enemy. The fort was attacked and placed under siege several times, but never taken.

It’s a delightful spot with historical explanations, rooms to explore, and tons of cannons that the kids will love checking out. The views of the city and the Matanzas River are terrific.

BLACK HISTORY

The Lincolnville Museum and Cultural Center is a fine spot housed in an old high school in what was the city’s Black district for many years. It’s now getting the gentrification treatment, but the museum is here to help preserve important stories about Black residents in the oldest continuously inhabited European-founded city in the U.S.

You’ll find inspiring exhibits about locals who made a difference, as well as horrifying stories about racism, lynchings, and the area’s slave history. When I was there they also had displays about Black Buffalo Soldiers and famous Black Musicians who’ve played in the area, including Billie Holiday and Little Richard.

Martin Luther King Jr. came to the city in June of 1964 and was jailed for “unlawful assembly and civil disobedience” following a peaceful downtown protest. His fingerprints from his night in jail are on display at the museum.

In addition to the cultural center, Lincolnville is home to several plaques and markers that help chart the neighborhood’s rich Black history.

“People come to St. Augustine from around the world for the history,” said Floyd Phillips, the museum’s president. “But as far as I’m concerned, if you haven’t been to Lincolnville, you haven’t been to St. Augustine.”

A few miles north is Fort Mose Historic State Park. The fort was established by the Spanish governor in 1738 after 100 or so slaves escaped from South Carolina and made their way south. There are fascinating and often heart-breaking stories about those who lived here, including a man named Pedro Graxales who was in the Spanish militia and fought against the English, who had taken him from his homeland in the Congo. His wife was a slave, however, as were his six children. “I would rather live with my family, but I go to St. Augustine often to visit them,” he wrote.

VILANO BEACH AND LUNCH

Vilano Beach is a throwback kind of place that seems to be on the verge of gentrification, with new hotels springing up in the small downtown area. Still, there’s plenty of charm, including the Magic Beach Hotel, which features a neon sign with rabbits leaping from a black hat and white exterior walls with colourful pink flamingo carvings. It’s utterly delightful. The beach has a wide expanse of sand that’s perfect for strolling or even bike-riding given its firm nature. A few blocks west you’ll find Beaches Seafood and Spirits, where they have a nice mix of Florida/Caribbean cuisine and a fine patio and bar overlooking the Tolomato River and the city’s fishing pier. Order a blackened fish sandwich and an Ancient City beer, brewed in St. Augustine.

SHOP TIL YOU DROP

St. Augustine is a fabulous spot for shoppers. Cool and Collected is a fun vintage and antiques store on San Marco Avenue, between El Castillo San Marcos and the Fountain of Youth.  Antoinette’s Bath House is a lovely spot for bath products on King Street, in the heart of downtown. Outside of town off Highway 95 you’ll find the the St. Augustine Premium Outlets. You’’ll also find terrific galleries. When I was there, one of the downtown galleries was featuring works by both Dali and Dr. Seuss, an interesting combination if there ever was one. Butterfield Garage is a wonderful art spot on King Street, just a few blocks west of Colonial St. Augustine. You’ll find marvellous art from a number of local residents. I liked one of the paintings so much I bought it and took it home.

A CAFFEINE FIX

You might need to recover after your shopping spree. Just a short walk from El Castillo in the old quarter of town is a small, delightful spot called Crucial Coffee. There’s a tiny wooden cabin with books and a few small tables, and then a large, colourful garden that makes for an excellent retreat that feels more like Key West than northeast Florida.

A CLASSIC DINNER SPOT

Columbia Restaurant is an old home done up with courtyards and a series of rooms, some with glorious stained glass. There’s atmosphere to spare in this downtown classic. The restaurant opened in the 1980s but is part of a small chain of Florida places that date back to 1905. The 1905 salad is mixed tableside and features iceberg lettuce with baked ham, Swiss cheese, tomato, olives, grated Romano cheese, Worcestershire sauce and garlic dressing. The sangria is terrific, and they have excellent crab cakes and black bean cakes. The Gambas Al Ajillo has enough garlic to ward off a football team worth of vampires. Save your bread for soaking up the oil and garlic. Of course, there’s Key Lime Pie for dessert.

DAY TWO

LIGHTNER MUSEUM

The Lightner is a rather unusual museum, housed in the old, Spanish-inspired Hotel Alcazar (1888) in the heart of downtown. The grounds and interior courtyard feature gurgling fountains, classical statues and beautiful landscaping. The museum was created by Chicago publisher and collector Otto C. Lightner, who published Hobbies magazine. Inside you’ll find a wide array of unusual bits, including old typewriters, wood carvings, dinner plates, and a beautiful desk that is believed to have been owned by Napoleon Bonaparte’s brother. The old indoor swimming pool is a now a regal dining room. They also do more modern exhibitions, some of which are quite striking.

VILLA ZORAYDA

This is a small but intriguing museum a few steps from Flagler College and the Lightner Museum. Built as the private home of a wealthy Boston businessman in 1883, it’s a castle-like place modelled on the Alhambra in Spain. The house is filled with expensive and rare furnishings such as Asian desks and Moorish lamps in a series of rooms. The Egyptian room has a rug that’s made out of the hair of cats found along the Nile River and is said to be 2,400 years old. They say anyone who walks on the rug will be cursed. Luckly, it’s hanging on a wall and you won’t get the chance.

A FINE PATIO LUNCH

Catch 27 is a lovely restaurant in the old part of town, with both indoor seating and a pretty patio with a fountain. St. Augustine is famous for its population of residents who trace their ancestry to the Mediterranean island of Minorca, and Catch 27 offers a Minorcan seafood soup that’s quite tasty, and just a little spicy. The blackened fish tacos also are tasty, or try a Cuban rice bowl.

THE FOUNTAIN OF YOUTH

One look at this place from the outside and you immediately think, “Cheesy. Way too cheesy.” But I quite enjoyed my visit. The Fountain of Youth area is where Spanish explorer Ponce de Leon landed in 1513, allegedly looking for the legendary Fountain of Youth. There’s an indoor display featuring local native Americans and the European explorers, as well as a trickle of water that’s said to be the original fountain Leon discovered. I can’t say I felt any younger having had a sip, but I didn’t feel worse, either. The gardens are delightful, as are the strutting, colourful peacocks who call the grounds home. You’ll find displays of people doing blacksmith work or showing off how old guns were fired back in the day. There’s also a planetarium and remains of an old Timucuan Indian burial ground.

A REMARKABLE COLLEGE

Flagler College is a truly remarkable bit of architecture on King Street, right across the road from the Lightner Museum. Henry Flagler, the northern industrialist and colleague of John D. Rockefeller, who pretty much started mass tourism in Florida, built this as a hotel (The Hotel Ponce de Leon) in 1888. The courtyard is truly stunning, and the old lobby is just as remarkable. This was one of the first hotels to have electricity. The story goes that guests were afraid of the new technology, forcing Flagler to hire “flickers” who would go into people’s rooms and turn the lights on for them, lest they get electrified themselves. Stroll around the grounds until you feel at home, and then check out the Tiffany Glass in the old dining hall, which is said to be worth millions.

A WEE DRAM

Saint Augustine Distillery, conveniently located a few blocks from San Sebastian Winery, has won awards for its locally produced bourbon, which features Florida corn and Florida wheat and, as law requires, is aged in charred American oak barrels. They make a variety of bourbons, some aged longer and some finished in port barrels from San Sebastian winery. Their vodka is made with local sugar cane and is smooth and excellent. Their gin used Florida citrus, juniper and other botanicals. They do fun tours with engaging distillers who know their stuff, and there’s a nice tasting program.

A SPECTACULAR DINNER

Lena, an Asado dining experience, features food cooked over an outdoor grill, Argentina style. Owner Nick Carrera is from Argentina and grew up with food cooked an open grill, what’s called Asado in Argentina. He and his wife, Christie, have taken an old shrimping factory just west of downtown and turned it into a glorious food destination, with truly spectacular steak, as well as house-made chorizo soaked in Malbec wine, tasty chicken and perfectly grilled veggies. Lena Asado chef Matt Brown has worked in some of the area’s top restaurants, but told me he “got tired of putting micro-dots on a plate” and wanted to make real, honest food. Other items could include a pea cassoulet or sofrito-infused roasted duck. There’s a pretty patio under pale lights and an interior seating area I never got around to checking out. It’s about three blocks off King Street.

WHERE TO STAY

The Homewood Suites by Hilton makes a great base of operations. Rooms have a kitchen with a range, microwave and refrigerator, and plenty of space for a couple or a small family. There’s also a nice pool, free breakfast and wine and food receptions on Wednesday nights.

OTHER THINGS TO DO

Lots of cities offer food tours, where you stop at a variety of restaurants for different types of cuisine. The folks at The Tasting Tours go one better by matching your local food with great wine or drinks. The tours are a wonderful way to learn about the city, and the people and restaurants in town. The company started 11 years ago and now has a staff of 15. “You’re happy and full when you leave,” says founder Andrea Jones.

MORE INFORMATION

https://www.floridashistoriccoast.com/