Start the afternoon off with a trip to the National Museum of Women in the Arts (1250 New York Ave. NW) to see the wonderful exhibit "Italian Women Artists From Renaissance to Baroque." The show raises several gripping questions about a woman's place in the Italian Renaissance, as well as showcasing some excellent art from the time.
Then stroll up to U street, or hop on the Green or Yellow line, to stop at Grape Legs (1905 9th Street, NW), a wine shop that does several tastings a day. Run by the friendly Franco Clark, the inventory at this shop is both wide-ranging and affordable.
Then for dinner, head back down to the classic Italian-style A.V. Ristorante (607 New York Ave., NW). Though it may not look like much from the outside (it resides near some rundown parking lots and is in a boxy building), it's long served up classic and tasty Italian dishes to everybody from Supreme Court judges to senators. Plus, rumors have been swirling about its imminent closure this summer, so you should get in while the getting's good.
Need some help plotting out these locations? Check out this link, which provides a handy map to the spots recommended above.