Toledo is one of my favorite places in Spain, I think partially due to the setting. Toledo sits on a steep hill above the River Tagus (Tajo), which encircles about two thirds of the old city. The streets are narrow and the city’s walls, gates and bridges give it a real medieval feel.
Toledo is only about 72 km (45 miles) from Madrid, making it possible to visit as a day trip from Madrid. However, I would suggest staying at least overnight to enjoy the ambience of this town. A walk at sunset around the perimeter of the city is very romantic and peaceful.
There is plenty to see, including the 13th century Cathedral which has both Gothic and Baroque elements, the 15th century Franciscan Monasterio de San Juan de los Reyes (one of the great monasteries of Europe), the rebuilt Alcazar (castle) and many other churches. We also enjoyed just wandering the hilly narrow streets and around the old town’s walls. For additional good views, consider the tram ride that goes around the far bank of the Tagus River.
Due to its history as home to Christian, Jewish and Muslim cultures over the centuries, Toledo has a unique atmosphere – feeling a bit like Jerusalem as well as medieval Europe. Originally, the Romans settled here, followed by the Visigoths in the 6th century and then the Moors in the 8th century. Toledo was also home to the famous artist El Greco (“The Greek”) in the 16th century. We stayed in the heart of the old town at the Hotel Santa Isabel which has a great view from its rooftop.
Driving is a nightmare in the old city, so take advantage of the large parking lot outside the northern perimeter near the bus station, and just hike up into the old town.