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St. Augustine:
Upscale-
95 Cordova in the Casa Monica in St Augustine makes some great food. They have music depending on the day, mostly jazz. They used to have a duck dish that was absolutely delicious, but everything I've had there has been top notch. The Casa Monica is a beautiful hotel, and it's nice to check it out before you dine. Wife will likely love it.
Mid-range-
Harrys is great, just North of the Casa Monica on A1A. Great cajun-inspired dishes. I'd take Harrys over OC Whites and the brewery on the corner.
The Columbia is great, good food and a nice building.
There are more restaurants out on St Augustine Beach, pretty easy to judge most of them from their exterior.
Snack-
The Spanish Bakery, off St Georges, but behind a wall (follow the sign) has some cheap pastries and snacks, with a neat dining area.
I'd stay away from the Kilwins and other chocolate factories, it's overpriced and pretty poor, IMHO
Walking down St Georges you will find a couple of bars with friendly staff. There is an arcade of shops off to the side, I think there's a candy store and a weird jerky (like the meat) store near the front, and a really neat bar at the back.... Small, quiet, but with a great selection of beer, if that's your thing.
Hope this helps!
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