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St. Augustine: America’s First City

105 miles NE of Orlando; 302 miles N of Miami; 39 miles S of Jacksonville

America’s oldest permanent European settlement, St. Augustine draws history buffs and romantics to its Colonial Spanish Quarter and 18th-century buildings. With its coquina buildings and sprawling, moss-draped live oaks, visitors can do more than just museum hop. St. Augustine encourages guests to sit down for a while, and to drink in scenes from the past along with a chilled glass of sweet tea.

Tourism is St. Augustine’s main industry these days. However, despite the number of visitors, it’s an exceptionally charming town, with good restaurants, a small-town nightlife, and shopping bargains. Give yourself 2 days to tour the magnolia-lined streets of old St. Augustine, longer to fully savor this historic gem.