St. Augustine is a long-time family travel favorite, with Castillo de San Marcos to explore, an alligator farm, the Pirate Museum and Ripley’s Believe It or Not Museum to keep kids entertained. The 42 miles of beaches within easy reach further assure its popularity, with places for surfing, kayaking and even for finding fossilized shark’s teeth in the sand, onPonte Vedra Beach.
The long history of St. Augustine comes to life for kids by costumed interpreters and reenactments — often noisy ones — at the May 11–13 reenactment of Francis Drake’s 1586 raid on the Spanish town.
Part of the 2023 St. Augustine History Festival, the event includes an encampment of reenactors at the Oldest House Museum Complex throughout the weekend, with drills and 16th-century living history demonstrations on Saturday. The battle will be reenacted Saturday evening, beginning at Santo Domingo Redoubt near the City Gate and ending at Plaza de la Constitución.
Throughout the weekend, special programs will be offered by other historic and cultural sites, including free family programs at Ximenez-Fatio House Museum. Also new is a performance tour telling the story of the of the 225-year-old house from the perspective of its former enslaved residents. They Lived Here, as Well — Together will be presented on Thursday, Friday and Saturday mornings.
Families will enjoy getting outside and learning about Florida’s coast and can join free outdoor programs by naturalists at St. Johns County Parks and Recreation or park rangers at Anastasia State Park. The park has beautiful white-sand beaches as well as a campground.
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