It sounds to me like you're asking for something like what British expatriate Stephen Drake-Jones of The Wellington Society offers. He/They give historical tours of Old Madrid (or other areas - including Toledo) and he is QUITE the man. He's so witty and charming too. Your kids will love him.

There are many threads posted about his tours in the "Food, Drink, & Entertainment" forum including the " Madrid: The Wellington Society...Stephen Drake Jones " thread. I've taken a number of his tours and they're always educational AND entertaining. The 2 or 3 stops at tapas bars are great too - your kids will love these places too. Stephen Drake-Jones is far and away the most knowledgeable tour guide (or teacher) of Madrid that you'll find.

Saludos, MadridMan