Good shoes with strong arch supports are a must in this hilly cobblestone filled city.
Miscellaneous: Toledo must have been designed originally to confuse its enemies from successfully invading the City. There are a confusing series of streets with names of streets changing frequently.
Definitely it is important to get a good map. The one given out at the tourist information center is ok but there are much better sources. I recommend going to the site go-toledo.com which has two excellent maps. The first relies on Google earth technology and provides details on individual streets but not city landmarks. The second map, which can be printed out, is linked to four excellent series of walks through Toledo. The maps, along with the short walk texts, provide outstanding information on four great walks through this amazing City. There is a short description of the more than 30 sites they call out on their walks. Best part of it is that it is free!
Clothing/Shoes/Weather Gear: Forget about wearing high heels in Toledo - the small cobblestone streets are very charming but slightly uneven, and as the entire portion of the city within the walls is built up on hill, you'll spend the entire day either going down or climbing up some more or less steep hills. And as there is no denying that this city is best seen on foot, if you want to make the most of your time there, I'd highly recommend bringing a pair of comfortable walking shoes.
Miscellaneous: just around 60min from Madrid, one does not need much packing...but have good footwear, you are on your feet a lot, suncream and lip protection...this City is a hot place...right from May till oct. the narrow streets just keep the heat 'conserved' and throws it right into to face again, keep your fluids up!!
Miscellaneous: If you are coming from Madrid, on a budget and visiting Toledo on a day-trip, would be wise to buy your mineral water and little snacks before enterign the boundary of the old town. Toledo Old town is pricy.
Miscellaneous: Get a free copy of map from the Spanish tourist office near the bus stop. Though it could be difficult sometimes to find your way out into the old town which was built on hills.