Castilo St. Augustine

Florida’s fountain of youth

Executive summary by darmansjah

History books taught us that Spanish explorer Juan Ponce de León “discovered” Florida 500 years ago in 1513 while seeking the fabled fountain of youth. But before the peninsula was claimed by de León, it was home for more than 12,000 years to Paleo-Indians who built civilizations around its water-filled sinkholes and left behind archaeologically rich middens (giant piles of oyster shells) as proof of their bayside existence.

Today, finding a genuine slice of “Old Florida” can be a scavenger hunt. The breezy Spanish colonial city of St. Augustine is an exception to the rule. A pair of marble lions greets visitors crossing the regal Bridge of Lions into the walled city. Looming over it is Castillo de San Marcos, a 17th-century fort surrounded by a moat and occupied at various times by Spanish, British, Confederate, and U.S. soldiers. The fort’s warren of chambers echoes with the stories of pirates, three signers of the Declaration of Independence, Spanish-American War deserters, and even Seminole Chief Osceola, who was incarcerated here in 1837 for leading the native resistance against the U.S.

Along King Street sit historic Flagler College and the Lightner, an antiquities museum housed in an 1887 Spanish Renaissance Revival masterpiece. It was commissioned by oil tycoon Henry Flagler, who is credited with salvaging the city and planting Florida’s tourism seeds. St. George Street, St. Augustine’s main drag, may have become overly touristy and crowded with T-shirt emporiums and fudge shops, but the side streets still harbor scrubby garden courtyards and off-the-radar bars, such as the 130-year-old Mill Top Tavern, where you can imagine what Old Florida was like before it became the Sunshine State. —Adam H. Graham

Travel Tips

When to Go: Spring (March-early June) and fall (late September-November) average temperatures are a comfortable 70-85ºF. Keep in mind that Atlantic hurricane season is June-November.

Where to Stay: Stroll from the intimate St. Francis Inn bed-and-breakfast in Saint Augustine's brick-paved historic district to nearby restaurants, shops, galleries, and museums. Or watch the sun rise over the Atlantic from the oceanfront House of Sea and Sun, a comfortably elegant 1920s Flagler heiress’ home turned bed-and-breakfast on St. Augustine Beach.

How to Get Around: The Old Town Trolley narrated tour route encompasses 22 hop-on and hop-off sightseeing stops, plus a free shuttle to St. Augustine Lighthouse & Museum. Purchase three-day passes online ($21.32 adults, $9.27 ages 6-12).