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So I think O'Leary's is probably the nicest high end seafood restaurant in Annapolis. The service is normally always professional and prompt. The wine list is well decent for MD standards. The seafood is good. All the dishes have horribly stuffy titles and descriptions, but it really is pretty solid. And they run specials with local caught fish. It is a very small little place, and sometimes the prices are steep in Annapolis standards, but pretty normal if you compare to DC. I eat here from time to time with my Mom on special occasions and it is always a really nice meal. I tend to order the thing with the least fussiness and that seems to work well for me.

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