Birthday dinner Winter Park/Orlando
maybe fiddlers green irish pub? casual, not overwhelming, good solid fare, good beer. and fun! although, not knowing what you really mean by "sheltered", maybe a pub might not be such a good choice ;)
i don't eat in winter park very often so i'm not much help. if you plug "winter park" into the search engine you can find some recs by looking at the more recently dated threads. then look up the names of anything that intrigues you on google.com.
Houston's is very nice, I really enjoy heading out back by the lake with a glass of wine.
Del Frisco's on Lee Road for steak.
Lots of choices on Park Ave. and Winter Park Village,
For Winter Park area places with good solid, not cutting edge food in a pleasant atmosphere, these come to mind:
Briarpatch, Pannullo's and 310 Park, all located on Park Avenue. Chef Justin's is also good, a bit higher priced, and can be noisy and crowded at times.
In the area around Hannibal Square, Hot Olives is quite pleasant as is Chez Vincent for French food.
In the Winter Park Village, she may like the quiet, clubby, but expensive steaks and other items at Ruth's Chris. Brio Tuscan Grille is also pleasant and, if she's feeling a little adventuresome, the Americanized Asian food at P.F. Changs is nice.
Definitely Houston's and for some nice Italian, Rocco's
Hope that helps.