The oldest city in the United States is charming and an architectural delight. The history is fascinating. One of the best ways to get a feel for this city is on one of the many trolley tours. If 
you don’t get off, the full loop is about two hours. This will give you a good idea of what is of interest for further exploration.
Lodging comes in all price points. I saw signs for $35 on “the other side of the bridge” but to park in the parking garage it is $10. There is a Four Star revitalized historic hotel the Casa Monica, which is elegant and centrally located. It is next door to the small, quaint B&B we stayed in called The Old City House Inn, which was a perfect choice for us. Quirky, clean and historic, this place excelled in customer service and friendliness. I chose the Lightner room due to its small private balcony. We sat out on it each night in the wicker chairs. Breakfast was delicious and ample and served between 9-10. A fruit and cheese plate is included in the evening. The courtyard is delightful. There are two bikes available to guests and St Augustine is a bike friendly town. The restaurant at the Inn serves lunch and dinner and has a diverse menu. We also ate at O’Steen’s, which is a good choice for seafood.
Families will enjoy various activities from the original Ripley’s, a fort, beaches and a lovely carousel. There was a ghost tour, which looked like it might be fun. 
Mature adults will enjoy the arts, dining options, numerous museums and world class architecture. Art/collectible/antique shopping opportunities abound with many unique pieces being offered. By all means, do stroll after dark. This is a beautiful city during the day, but dramatic at night.
Season for this town is considered Jan-March, however we found it cooler than expected at 65 degrees so plan to dress in layers.
(This report written during a 2-night stay in late October, 2013)
