Two buses operate every day to and from Madrid's Estación Sur (trip time: 3 1/2 hr.). The road is poor, but the route through the surrounding regions is full of savage beauty. In Guadalupe the buses park just uphill from the Town Hall. Call Empresa La Sepulvedana, in Madrid (tel. 91-559-89-55; www.avanzabus.com), for schedules.
One narrow highway goes through Guadalupe. Most maps don't give it a number; look on a map in the direction of the town of Navalmoral de la Mata. From Madrid, take the winding C-401 southwest from Toledo, turning north in the direction of Navalmoral de la Mata after seeing signs for Navalmoral de la Mata and Guadalupe. Driving time from Madrid is between 3 1/2 and 4 1/2 hours, depending on how well you fare with the bad roads.