Madrid is well-known for Toreros (Bullfighters), a long and celebrated literary tradition, and its many sun-drenched plazas throughout the city. You can get ample amount of all three in Plaza Santa Ana, one of the city's most vibrant blocks. The Plaza is a place where locals mingle easily with tourists, both sipping wine in the sunshine on the lively terrazas and listening to street musicians playing classical guitar and the clarinet.
Located in the Huertas district in an area called the Barrio de la Letras (neighborhood of the letters), Santa Ana Plaza is just a few blocks from Puerta del Sol's central metro station. It's bordered on the east by the National Theater, the Teatro Espanol, which lives in a building that was originally built in 1785. On the west is the striking ME Madrid Reina Victoria Hotel, a newly redesigned luxury hotel housed in an architectural masterpiece that was originally built in 1916 and a favorite lodging spot for Madrid's famed Toreros in the past and celebrities like The Rolling Stones today.
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Under the plaza's two monuments that pay homage to the 17th century playwright Pedro Calderon de la Barca and the poet Federico Garcia Lorca are a slew of outdoor tables under large umbrellas – a relaxed vantage point for people watching while eating olives and drinking wine. When the sun goes down, head to the oldest Cerveceria (or pub) on the plaza, Cerveceria Alemana, which started serving drinks in 1904 and was a favorite haunt of Hemingway. Then, have dinner at one of the newest bars, the Ana La Santa restaurant on the ground floor of ME Madrid Hotel, which serves the best paella in the city.