3. St. Augustine, Florida: The Ancient City
Long before the English settled Jamestown or the Pilgrims landed at Plymouth Rock, the Spanish established St. Augustine. Founded in 1565, it is the oldest continuously occupied European-established settlement within the borders of the continental United States. Its narrow brick streets, Spanish Colonial architecture, and commanding stone fort make it a fantastic winter escape.
Costs & Passes: The crown jewel of St. Augustine is the Castillo de San Marcos National Monument, a 17th-century fortress built from coquina (a sedimentary rock made of shell). According to the National Park Service, the entrance fee is $15 for adults (ages 16 and older) and is valid for seven consecutive days. Children 15 and under enter for free when accompanied by an adult. Important note: The Castillo is entirely cashless—you must use a credit or debit card. Interagency passes, such as the Senior Pass, are accepted for free entry. In 2026, the NPS also offers several fee-free days, including Presidents Day, Memorial Day, and Veterans Day.
Getting There & Around: The closest major airport is Jacksonville (JAX), about an hour’s drive north. While having a car is helpful to reach St. Augustine, you will want to park it upon arrival. The historic district is dense and parking is scarce. We recommend buying a multi-day pass for the Old Town Trolley; it serves as both a narrated historical tour and a highly effective hop-on, hop-off transit system that saves you from exhausting walks in the Florida heat.
Crowd Strategy: St. Augustine is incredibly popular during the winter holidays due to its “Night of Lights” festival (late November through January), which draws massive crowds. If you want a peaceful historical experience, visit in late February or early March. Arrive at the Castillo de San Marcos right when it opens at 9:00 AM to explore the gun deck before the midday sun and the heavy crowds arrive.
