Established by the Spanish in 1565, charming St. Augustine is the oldest city in the United States. And for all its atmospheric colonial architecture and fabulous historical sites, this northeast Florida town is also a quintessential Florida beach burg, with an easy, breezy vibe. All the better for convincing the kids that cultural explorations can be fun, right?
Book a stay at the historic Casa Monica Resort & Spa, where your wee history buffs will be amazed they’re sleeping in a space first opened in 1888, as parents admire the property’s original artwork and ornate, Moorish columns.
Follow our suggestions for a lively itinerary that mixes history lessons and pirate treasure with family seafood dinners and the all-important ice-pop break.
If you see just one historical site outside of downtown, make it this imposing fortress — the oldest masonry fort in the U.S. — finished by the Spanish in 1565 and later used during the Revolutionary and Civil wars.
Kids feel like true explorers wandering through the now-dry moats and peering out to sea from the turrets. Time your visit for Friday through Sunday to hear canon-firing demonstrations thunder through the air.
Make sure to explain to the kids that the walls, 16 feet thick, were able to withstand British cannonball fire thanks to the absorbent qualities of the Florida coquina (a soft limestone made with shells and coral) used to build them.
Bonus: Kids 15 and under get free admission when accompanied by an adult.
For a good overview of all there is to do in town when you arrive, pile everyone aboard the Old Town Trolley for a roll-through tour of St. Augustine’s highlights. The ride couldn’t be more convenient for Casa Monica guests. One of the trolley tours stops is located across from the hotel.
The open-air trolley pulls several compartments behind it along the bricked streets of town, making 23 stops along a route that takes in highlights like the Old Jail, Castillo de San Marcos, St. Augustine’s oldest house and the Fountain of Youth. An entertaining narrative from your driver along the way makes the history lessons go down easy.
Tickets are good for three consecutive days and include on-and-off privileges, making this a convenient way to get around town, too. Pinching pennies? Admission to the St. Augustine History Museum is included in your fare.
While it only dates to 1874 — youthful by St. Augustine’s standards — this candy-striped black-and-white lighthouse and accompanying maritime museum on Anastasia Island have much fascinating history to share.
Tire the kids out with a climb of 219 steps up the tower for views overlooking Matanzas Bay and the Atlantic Ocean. Then visit the watchkeeper’s house, now a museum, to see artifacts from doomed ships that wrecked in the area.
General admission includes a guided tour of the lighthouse’s history that delves into the art of wooden boat making, too. Kids can even embark on a maritime scavenger hunt to discover animals living in the coastal hammock here and learn about the historical medicinal uses of local plants.
The first hint they’re about to have a blast comes when kids get a treasure map to the exhibits at this pirate-themed museum overlooking the Castillo de San Marcos. A mix of Hollywood and history maximizes fun.
Kids can see the sword prop Johnny Depp used as Jake Sparrow in “Pirates of the Caribbean” and feel the heft of a real gold bar recovered from a Spanish galleon when they reach inside a glass case. Actual pirate treasure and authentic treasure chests are also on display, and kids can fire a cannon from a gun deck, too — good luck getting them to leave, in other words.
Walking around St. Augustine’s old town to see the sights is sure to work up an appetite. Open for lunch and dinner right across from the St. Augustine Visitor Information Center, Barnacle Bill’s homestyle restaurant dishes up fried and broiled seafood specialties that fill tummies without breaking the bank.
There are daily fish offerings, as well as burgers and salads, and the excellent Minorcan clam chowder is a local favorite. The kids menu has such favorites as shrimp baskets, fried fish, and mac and cheese.
Dessert, anyone? When something icy and sweet is just what it takes to coax the gang through another history stop, this artisan ice-pop shop near the pirate museum and Castillo de San Marcos does the trick.
Made from pure fruit and fresh herbs and spices, with a touch of cane sugar and limited dairy, the ice-pop selection changes seasonally. You might find watermelon ice pops in the summer and pumpkin pie flavor come fall.
Roughly 200 years after they built Castillo de San Marcos, the Spanish constructed this other famous defense system for St. Augustine, in 1740, to protect the city’s southern entrance from British attack.
The small fort sits on a barrier island, and visitors reach Fort Matanzas via a short, free ferry ride across the Matanzas River, putting the joy in the journey for the kids in your group who will surely feel like pirates making landfall.
To explore inside the fort’s walls and see its canons, you have to climb a short series of stairs up from ground level. From there your little adventurers will surely want to ascend a few more steps up a steep wooden ladder to the top of the fort, where soldiers once scouted for approaching ships.