Hey ToniG, have you tried arranging a Tapas tour with Stephen Drake Jones of the Wellington Society? Stephen is a walking Madrid encyclopedia and historian and comes highly recommended, his website is at
www.wellsoc.org but reserve early as he is a VERY busy man and highly in demand.
Also look into what Andr�s and his cronies have to offer at
www.walksofspain.com. I have heard good things about his Tapa tours and I think he usually deals with a younger (though not necessarily hipper

) crowd. You will not get the rich history that you do with Stephen and the Wellington Society but it is another good option.
Maybe you should look into both.
As for guided day trips to El Escorial, Toledo, Segovia, etc..., I know Andr�s and company do not do them but Stephen does (not sure how many people minimum are rewuired for a special trip but he may have one already planned that you can tag along with.
Again, that is:
The Wellington Society:
www.wellsoc.org Walks of Spain:
www.walksofspain.com Saludos,
jer...