One night in Poughkeepsie/Rhinebeck
Having been a recent graduate of the CIA itself, I can tell you first hand that the Italian restaurant, also known as the Colavita Center, Is a magnificent place to go. The high ceilings and chintzy Spanish chandeliers may throw you off, but the food is very much worth the trip. If you're not in the mood to feast, the al forno area in front of the kitchen is perfect for "small eats", and does not require a reservation. However, if you're feeling a little frisky with Florentine focus, look no further than the bistecca alla fiorenta. Built for two, it's massive, and most certainly delicious.
First and foremost though, don't take my word for it, go ahead and give it a whirl.
By the way, I am in no way shilling for the CIA. I'm just very enthusiastic about food.