DnvrFox---Hi--I live in Jax and I visit St. Aug about once a week. Nice place--Plenty of condos for rent, believe me. If you stay on Anastasia Island, the beach is right at your footsteps. The drive to Orlando is very easy--45-60 minutes. If you like parks---Alligator farm is good. Fort Matanzas is good--you take a boat ride over to the fort.
You have to eat at Caps---couple miles north of St Augustine off of AIA--restaurant is located on the Intracoastal Waterway. Sit outside and enjoy the waterway. Also, Casa Monica hotel is great for a nice romantic meal (little expensive). My wife and I eat breakfast their about once a month. Another favorite of mine is Cortese's Bistro and Martini Bar located across for the merry-go-round. Just ask anyone where the merry-go-round is. A guy plays a guitar on weekend nights and it's nice to sit outside under a canopy of live oaks (great wine).
My wife and I take our bikes down about once a month and ride through the city all through the back streets. Go down by the National Guard armory--really pretty section of homes and the military cemetary is very moving. Oh -their are many B and B's in St. Aug. Traffic is not that bad--they are rebuilding the Bridge of Lions and a temporary one has been built that takes traffic across to the island. Anastasia Island's traffic isn't bad. I do a lot of photography so I am all over the place down there and it's very enjoyable. I've followed a pair of nesting eagles for 4 years and have never had any traffic woes. The Ospreys are all over the place especially down by Marineland--nice place also to visit--My favorite beach in St. Aug is Matanzas---just south of SR 206 on A1A---Beautiful beach that connects the ocean with the Intracoastal---only other advice is to stay away from the tourist trap restaurants--the ones I mentioned are great--go eccentic and find some small off the main drag little cafe's. The weather is getting warmer here so it should be a lot of fun for you---The trolley is a good thing to take that gives a lot of history and of course the horse and buggy. Have fun and let me know if you have any questions--