Start the route in Plaza Zocodóver, the neuralgic centre of the city. Note the beautiful gate leading to hill called Cuesta de Santa Fé.
Leaving the square along Carlos V Hill, you'll come to the Alcázar of Toledo, undoubtedly the most impressive building in the city. In the 3rd century it was a Roman palace, and later it was renovated and eventually served as a fortress. Today it houses the Biblioteca (library) of Castile-La Mancha and the collections of the Military Museum. It's worth seeing from the outside, although the most impressive view is from the outskirts of the city.
If you go down Calle General Moscardó, one of the side streets of the Alcázar, you'll come to a large square with a viewpoint with amazing vistas of the opposite bank of the Tormes River. To your left, is Castillo de San Servando (San Servando Castle), and in front the impressive Academia de Infantería (Infantry Academy).
Behind this square is the church Iglesia de San Miguel. Walk up San Justo Hill until you reach the square and church of the same name. There you'll find a Taberna Enebro, a reliable local chain where for every draft beer you order (2€), they serve you one tapa for free (if you wish, you can do this after visiting the cathedral).
Next, go up Calle Sixto Ramón Parro, which will lead you to one of the side streets of the cathedral. We recommend turning right and circling the church, admiring its walls, doors, large windows and towers. On the right on the same street, note the curious alleys Infierno (Hell) and Diablo (Devil).
After going down Calle del Hombre del Palo, you'll come to Plaza del Ayuntamiento (City Hall Square), where the archbishop's palace (to the right) and City Hall (in front) are of particular interest.