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For History Buffs: St. Augustine
It isn't surprising that the oldest permanent settlement in the United States would be chock-full of history. The city of St. Augustine is captivating from the get-go -- its narrow cobblestone streets and European architecture make it one of the most charming places in Florida. The Old Town is where you'll find many of the historic sites and attractions, such as Castillo de San Marcos (which dates back to the late 1600's) and Old St. Augustine Village, a group of restored period buildings.
Also worth a stroll is the campus of Flagler College, home to the circa-1887 Hotel Ponce de Leon. Built by wealthy industrialist Henry Flagler as a luxury resort, it's now a National Historic Landmark and the centerpiece of Flagler's attractive campus. For outdoor activities, head to Anastasia State Park with its opportunities for swimming, beachcombing, hiking, biking and boating.