St. Augustine, Florida

Founded by the Spanish in 1565, 55 years before the Pilgrims reached Plymouth, St. Augustine is where Florida's European history starts. The Castillo de San Marcos is the oldest masonry fort in the continental United States, built of coquina, a stone made of compressed shells, and it never fell to an enemy in battle. Walk the old streets early in the morning, before day-trippers arrive, and climb the ramparts for views over Matanzas Bay. The town gets busy on weekends and during the holiday light displays, so midweek in winter is the sweet spot.