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San Mateo has something for everyone when it comes to dining.
One 25th Avenue, you'll find Thai, Chinese, Italian, Vietnamese, Persian, Japanese, Greek and Brazilian dining options, as well as an independent coffee house and an old-fashioned diner. Be sure to try Nipa Pon for Thai food (the mussamun, Thai iced tea and sticky rice with mango are especially good), and the Yamasaki Bakery for a wonderful selection of baked goods, savory and sweet.
37th Avenue features a good Italian deli (G&G), a nice BBQ place (Lil' Biscuit House), a large meditteranean deli and grocery, an ice cream and cannoli shop (Romolo's) and a bad Mexican restaurant (Fernando's).
Downtown San Mateo (2nd Ave. through 5th, off El Camino) has a large selection of restaurants, all in an easy-walking retail area. Try Central Park Bistro for a nice selection of entrees and "small plates," Kingfish for New Orleans cuisine and ambiance, 3 Amigos for authentic Mexican food and Jeffrey's for fantastic hamburgers, shakes, etc.