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St. Augustine, Florida
The root: Founded 1565 — the oldest continuously inhabited city in the continental U.S., Spanish stone streets 55 years ahead of Jamestown.
Eat: Columbia Restaurant — Florida's oldest restaurant, Spanish-Cuban fare on St. George Street; The Floridian — Southern comfort downtown; Conch House — waterfront Caribbean-flavored seafood.
Skip — don't: The pirate-themed "old Florida" buffets off the main drag — the real Spanish and Minorcan food is on the pedestrian streets, not in the costume shops.
Specialty: Spanish colonial heritage — coquina stone, Minorcan clam chowder, and the oldest street grid in the nation.
Shops & crafts: St. George Street's colonial-era craft shops; Spanish lace, pottery, and Minorcan cookbooks; Castillo souvenirs with real coquina-stone carvings.
See: Tour the coquina Castillo de San Marcos; browse St. George Street's colonial shops; see Flagler College's ornate Gilded Age halls.
Main Street: St. George Street — a pedestrian lane of coquina and tabby walls, balconies overhead, the oldest platted street in America.
After dark: A ghost tour through the lamplit old city, or a quiet drink on a St. George Street courtyard patio.
When — events
Nights of Lights (late November–late January, millions of lights)
St. Augustine Food + Wine Festival (May, approx.).
Event dates are the typical annual timing; confirm with the town before traveling.