St. Augustine Old Town

Steve’s take

The oldest city in America, and it shows in the best possible way. The Castillo de San Marcos is a real 17th-century Spanish fort that your kids can run around like tiny conquistadors. St. George Street has enough ice cream shops and toy stores to keep everyone happy. About fifteen minutes off I-95 — this is a half-day stop that makes your road trip feel like a vacation instead of a forced march. Highly recommended by the Griswold family.