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Columbia Restaurant in Old Town was one of the best places I have eaten. Great food, beautiful Spanish atmosphere, and a separate gluten free menu. Service was great, very helpful on assisting me with options. Try to make a reservation. We were lucky and got in after a short wait because we went early. A lot of snowbirds are starting to head north now.
The Columbia House in downtown St. Augustine can accommodate.  It's a local favorite.  Also, Matanzas Innlet Restaurant in Matanzas, which is on AlA along ocean a few miles south of St. Augustine.  They have a dedicated kitchen. Very casual and you can eat outside by the water. 

We always eat at a restaurant by Matanza's Inlet south of St Augustine.  It is about a mile from Marineland.
The chef is a celiac and they have a number of gf Italian and seafood dishes, pizza, cheesecake, etc.

We just returned from St. Augustine. We had an excellent   dinner at Cap's
on the Water. I had an exquisite  curry chicken/shrimp  dinner. I'm not a
seafood junkie and they made me a special  dinner without the shrimp. They
were knowledgeable about gluten free and the waitress checked everything
with the kitchen.  

Our FAVORITE place is The Floridian. Its right downtown and the chef has celiac so they are so good about making things GF and have things marked on the menu that are or can be made GF. My favorite is the Blackbean Sweet potato burger. 

Another great place is The Present Moment Café. It is all GF but it is also vegan and raw. Their stuff is delicious, but I know some people may be hesitant with it being vegan and raw. Everything I have ever had there is amazing.

If you are going to the beach, its down aways, but the Purple Olive is also incredible and they have a GF menu. It's a little more expensive but nice for a night out. Its in a little strip mall and doesn't look like much, but the food is so good!  

Those are the 3 places I feel totally safe at and have never had a problem. There is also the Manatee Café, which does GF wraps and sandwiches, but it's a little north of down town off of state route 16. They are really good too. It's a good light lunch place. I don't know if they do dinner. 

There is a great bar called JP Henleys and they have lots of cider options if you are with someone that likes beer. They have over 40 beers on tap and a few ciders on tap and in the bottle. Its good for options! 

Try the Floridian.  Here is the link to the menu:

http://www.thefloridianstaug.com/menu/

They are very knowledgeable about gluten.
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