So I went to Osteria with the Mom last night. It was pretty quiet at first, but more people started to arrive as we got apps. My first reactions: Great menu, but it is pricier than a lot of Annapolitans seem to think restaurants should be (I am from DC so it didn't seem bad to me).
We started with the Cantaloupe and Prosciutto appetizer which was good fresh and the fruit perfectly ripe. We split it and it was certainly enough for us. I ordered the Pheasant which I thought was very good. It was kind of similar in taste to Chicken Cashel Blue at Galways Bay/Kilarney House with the wrap of prosciutto on the outside. It was stuffed with a pesto and veggie interior which was very good. I liked it, I didn't think it was anything extremely new or different, but had excellent flavors and was very satisfying. The veggies served with it had great flavor, and the mashed potatoes were mashed potatoes. Mom had the Gnocchi which was decent, but if you have ever had Gnocchi at Palena you will be disappointed here. Mom wished she had ordered a fish dish because all the ones coming out looked and smelled incredible. The portions were large, we probably didn't need an appetizer we were stuffed. For dessert she had Cappuccino I had the Italian ice cream which was so good. I had sworn I wasn't hungry enough for dessert, but I devoured this. It was cappuccino flavored ice cream with some chocolate in the center served with fresh strawberries, really good.
The service was great, everything arrived at just the right moment. The bread was good and warm, the space gave you a good amount of privacy and the booths were very comfortable.
I would say I like O'Leary's and Carrol's Creek better, but I really did enjoy it.