Amelia Island offers more than just endless days of leisure and warmth. As the only American territory to have existed under eight different flags, there is a history of rich cultural traditions. Cruise down Centre Street for a flavor of Civil War era history. Stroll past pastel-hued Victorian homes, restored colonial buildings and the Amelia Island lighthouse – the island’s oldest standing structure. At the northern tip of the island lies the picturesque town of Fernandina Beach, a charming historic port where the most stressful activity you’ll encounter is watching the crimson sunset from an outdoor cafe.

Fun Fact: In terms of land area, Jacksonville is the largest city in the continental United States.