Most of the recommendations I´ve seen here are for touristy "Flamingo shows" (exactly!) However, Madrid has the best Flamenco scene outside of Andalucia as many performers, for example from my hometown of Jerez, go to Madrid on a regular basis to work. If you can navigate through the Spanish, try www.tristeyazul.com, get to the main page, and click on the link "Cartelera". There are quite a good number of good venues, such as the peña flamenca "El Duende" or Sala El Juglar in Lavapies. Not all of it is going to be flamenco dance, but it will be "auntentico"!

Mike have you considered a day trip to Toledo?

Andres:
We would like to consider a day trip to Toledo...
Do have a suggestion for us?

Berzabuena:

Many thanks for the tips onnon-touristy Flamenco viewing. My best friend who will be travelling with me is a Columbiana, so navigating Spanish will be easy. Thank you again for all your help.
Cheers! Michael

Hola todos! Soy musico de Irlanda y ahora vivo en Madrid, estoy buscando un bar/cafe en donde es posible tocar un concierto, solo yo y la guitarra. Tengo mucho experiencia tocando en vivo en Irlanda. Toco como blues,country/folk y pop. Ademas tengo un monton de canciones originales. Can anybody steer me in the right direccion? Soy prof de Ingles tambien(CLARO). Realmente creo que el mundo deberia escuchar mi musica! He estado practicando casi un anyo y estoy bastante preperado. Por fi! Ayudame
El Country T

My suggestion is that you stop considering the trip and start planning it. You just need to catch the bullet train at the Atocha station and a historical map/bookguide of the city. I recommend you the map of Toledo La Libreria (Mayor st, 80) sells.