Upstream on the Tajo river, the N-400 road marks the border between Toledo and Madrid, very close to Aranjuez and by taking the Andalusia road, we reach Ocaña, one of the most monumental towns in the province of Toledo.

Its stunning main square is an excellent starting point for exploring its rich heritage. On the same square –where the Tourist Office is located– we come across the Town Hall façade. The town’s coat of arms can be seen on the main door.

The ecclesiastic heritage is rich and varied with the convents of St. Joseph, Santa Clara and Santo Domingo, and its Porticum Salutis interpretation centre. The churches of Our Lady of the Assumption and St. John the Baptist are home to most of the images and brotherhoods that give the town’s famous Holy Week its reputation. It is a Festivity of National Tourist Interest. Only the imposing tower of the San Martín Obispo church remains.

The civil works are spread around the whole town and bear witness to the importance that this town’s activity gave them at the time. The noble homes, such as the Count of Mora’s Palace, the House of Captain Pozuelo Espinosa or the Cárdenas Palace are highlights. As a crowning touch, visit the Fuente Grande (‘Large Fountain’), a work by Juan de Herrera, the architect of Philip II.

The route continues south until reaching La Guardia where highlights include the palace-house of the Jaenes, which is home to a museum; the church of Our Lady of the Assumption; and near the castle ruins, the chapel of the Holy Child located in what was the old Jewish quarter. It’s worth stopping at the town’s unique “caves”, which remained inhabited until the second half of the 20th century.

We can return to Toledo via Tembleque, with its iconic and unmissable main square; Mora, with its Peñas Negras castle and the Hermitage of Santa María la Antigua; Mascarque and its church of St. Mary Magdalene or the Juan de Padilla castle; and Almonacid de Toledo, with the remains of the castle dominating the town.