Go into the Mudéjar cloister — the sanctuary was rebuilt in Toledan Mudéjar, which is not what anyone expects of a royal Castilian monastery

Go into the sacristy, built 1636–45, which is reckoned one of the most dazzling Baroque sacristies in Spain

Work out the sequence of styles piled on one building between the 14th and 18th centuries

Find out how it started — a shepherd, a hidden image, and a king who won a battle in 1340 and paid up

Drive or walk into the Villuercas around it and see how remote a place this actually is

Alfonso XI credited his victory at the Salado in 1340 to a Virgin found years earlier by a shepherd near the river Guadalupe, and built a church where the hermitage stood. What grew out of it over the next four centuries is a monastery containing Gothic, Mudéjar, Renaissance, Baroque and neoclassical work layered on top of one another, in a village in the middle of the Villuercas mountains. It was made a basilica by Pius XII in 1955 and a UNESCO World Heritage Site in 1993, and the Virgin is patron of Extremadura.

Guadalupe: The Monastery in the Mountains

Stand in the Plaza Mayor and work out that the palaces around you were paid for with American silver

Find the equestrian statue of Francisco Pizarro and read what is said about him on the plinth and what is not

Find out who Francisco de Orellana was, what happened on 12 February 1542, and how he died four years later

Climb to the castle, an Arab alcázar before it was a Christian one, for the view over the plain

Go into Santa María la Mayor, the 13th-century church in the upper town, and find the tombs of the families who financed the expeditions

Francisco Pizarro, who took Peru, was born in Trujillo. So was Francisco de Orellana, born here in 1511, who came down the Amazon in 1542 and died on it in 1546. A great many other men left this small, poor town on the Extremaduran plain for the Indies, and the ones who came back rich built the palaces that now line the Plaza Mayor — which is why a town of a few thousand people has a square of that scale. Pizarro's equestrian statue stands in the middle of it. Above the town is the castle, originally an Arab alcázar.

Trujillo: The Town That Conquered Peru

Stay in or walk round the castle, one of the first paradores in Spain, opened in 1930

Work out what the parador network was set up to do and whether it worked

Look south from the walls to the Sierra de Gredos across the Campo Arañuelo

Find the Mudéjar tower in the town below the castle

Oropesa's castle was the seat of the counts of Oropesa, and in 1930 it became one of the first paradores in Spain — the network of state hotels in historic buildings that was set up precisely to keep buildings like this standing by giving them something to do. It looks south over the Campo Arañuelo to the Sierra de Gredos, which is one of the better views from a hotel window anywhere. The town below has a Mudéjar tower and the parish church, and the ceramics tradition here runs into Talavera next door.

Oropesa: A Castle You Can Sleep In

Go into the basilica of the Virgen del Prado and work out how many centuries of tile are on the walls

Watch a workshop throw and paint, and work out how much of the design vocabulary is Islamic in origin

Find out who Jan Floris was and what Italian technique he brought here around 1558

Find out what UNESCO inscribed in 2019 and which Mexican towns share the listing

Go on to El Puente del Arzobispo, which is part of the same inscription

Talavera has made glazed earthenware for five centuries, and the design, forms, glazes and decoration are Islamic in origin — plant and animal motifs that shifted to human figures under the Christian kingdoms. It took on industrial weight from the 16th century, and in about 1558 the Flemish master Jan Floris brought Italian technique into the workshops. Its commercial monopoly fought Seville for centuries and then lost ground to Alcora in the late 18th; the French army destroyed the kilns and factories between 1810 and 1812. UNESCO inscribed it in 2019 together with Puebla and Tlaxcala in Mexico, as one tradition across two continents. The basilica of the Virgen del Prado in the town is covered in the tiles, inside and out.

Talavera de la Reina: Blue and Yellow Ceramics

Watch the vultures at Peña Falcón, the rock face above the Tagus, in Monfragüe National Park, home to the world's largest colony of cinereous vultures with over 300 pairs

Climb to the Castle of Monfragüe at the park's eastern end for views over the Tagus valley

Look for Spanish imperial eagles and black storks around Villarreal de San Carlos, the only village in the park, with a population of 28

Stay after dark for the stars, since Monfragüe was recognised as a dark-sky preserve in 2016

Monfragüe is dehesa — the Iberian oak savannah that centuries of grazing and pig-keeping produced, open woodland over grass — plus the gorge where the Tagus cuts through a quartzite ridge. The combination makes it the best raptor site in Europe: over three hundred pairs of cinereous vulture, the largest colony of the species in the world, along with griffon vultures, Egyptian vultures, black storks and Spanish imperial eagles. You watch them from the road at Peña Falcón, at eye level, which is not an experience most places can offer.

Monfragüe: Vultures, Eagles and Dark Skies

Go into a secadero and see how it is done — slow oak smoke, upstairs, for days

Taste all three grades side by side: dulce, agridulce and picante

Go to the pimentón museum at Jaraíz de la Vera, which is also where the regulating council sits

Work out why the smoke is not a flourish: slow smoke-drying is what makes the colour and aroma keep

Buy a tin from a mill in the valley and compare it at home with supermarket paprika

Hungarian paprika is air-dried. Pimentón de la Vera is dried over slow oak smoke in two-storey drying houses, which is why it tastes of smoke and why the flavour, aroma and colour hold for so long — the dehydration is slow and gentle. It has been a protected designation of origin in the EU since 22 August 2007, grown and processed in La Vera, Campo Arañuelo, the Ambroz valley and the Alagón and Árrago valleys in northern Cáceres, and the regulating council sits at Jaraíz de la Vera. It comes sweet, bittersweet and hot.

Pimentón de la Vera: Smoke, Not Sunshine

Go into the imperial apartments and find the window through which Charles V heard Mass from his bed

Find the chair built for a man who could no longer walk and had to be carried

Work out what he gave up: Spain, the Netherlands, Naples, the Empire — abdicated, then this

Walk the gardens and the pool he had made below the terrace

Drive the Vera valley around it and work out why, of everywhere he owned, he chose here

Charles V ruled Spain, the Netherlands, much of Italy and the Holy Roman Empire, abdicated the lot, and came to a Hieronymite monastery in a wooded valley in northern Extremadura to wait for the end. He lived here from 1556 until he died on 21 September 1558. He was crippled with gout, so his rooms were built beside the church choir with a window through which he could hear Mass from his bed, and a chair was made specially so he could be carried. Yuste was named a European Heritage site in 2007.

Yuste: Where the Emperor Went to Die

Walk across it and work out that until 2025 this was a functioning road bridge carrying 237,000 vehicles a year

Stand at river level and look up 58.2 metres at piers that start from different heights of bare rock

Find the inscription on the central arch naming Trajan and the towns that contributed to the cost

Work out where the road went: Augusta Emerita to Bracara Augusta, through country Rome wanted for its metals

Look at the new bridge opened on 20 October 2025 and work out what taking the lorries off has bought

The Roman bridge at Alcántara carries the road from Augusta Emerita to Bracara Augusta over the Tagus: 194 metres long, 58.2 metres high, six arches of unequal height on five piers rising from different levels of rock. The central arch names Trajan and the towns that paid for it. It has been repaired by Charles V and by others, and until very recently it was still carrying about 237,000 vehicles a year — an unrepeatable piece of Roman engineering doing daily work as a road bridge. A replacement opened on 20 October 2025 and finally took the traffic off it.