Family Friendly St. Augustine: Old City
The historic district between the Castillo de San Marcos and the Bridge of Lions: the pedestrian blocks of St. George Street, the brick lane of galleries on Aviles Street, and the bayfront along Avenida Menendez. The densest run of restaurants and bars in the city, many of them in buildings with a century or two behind them.
An outdoor amphitheater under what the park calls the city's second oldest live oak, just off the busiest block of St. George Street, with seating for more than 250. Shows are free unless noted and open to all ages, usually 7 to 10 p.m., and it is a Sing Out Loud Festival stage in September.
Old Florida home cooking on St. George Street for more than 35 years: gator tail, fried green tomatoes, shrimp and grits. The name honors the original Cracker cowboys, and the garden patio welcomes dogs, which the cafe says on its own site instead of leaving you to guess.
A house with a longer resume than most of the city: Don Miguel Ysnardy built it around 1790, it served as one of St. Augustine's first hotels, and in 1961 it was moved to this spot on the bayfront. The O.C. White family has run it since 1992, with a garden patio, a balcony for the sunset over the bay, and live music in the evenings.
A flower-filled courtyard and upstairs bay views make Saint a tempting Italian dinner spot. Explore the menu and seating choices, then book the table you want.
A fast casual seafood counter on St. George Street built around wild American shrimp, Minorcan chowder and a datil-buffalo shrimp, with a kids section on the menu. It shares the Colonial Quarter with the Colonial Oak Music Park, which is where its live music happens.