Rising dramatically from the banks of the narrow Jerte River and backed by the peaks of the Sierra de Gredos, this town was founded by Alfonso VIII in 1180 after he captured it from the Moors. Plasencia’s motto, ut placeat Deo et hominibus (“To give pleasure to God and men”), might well have been a ploy on Alfonso’s part to attract settlers to this wild, isolated place on the southern border of the former kingdom of León. Partly destroyed during the Peninsular War of 1808, Plasencia retains less of its medieval quarter than other Extremaduran towns, but it still has extensive remains of its early walls and a smattering of fine old buildings, notably the Casa del Deán. The city makes a good base for side trips to Hervás and the Jerte Valley, the Monasterio de Yuste and Monfragüe Nature Park, or, farther northwest, to the wild Las Hurdes and Sierra de Gata. It’s also a stop along the Vía de la Plata, or Silver Way, an ancient Roman road several hundreds of miles long that’s become popular among cyclists and hikers.