Go into the monastery begun on 7 May 1529 and find the Plateresque east wing, which was built first

Work out what Caput Ordinis meant and what the Order of Santiago ran from this hill

Find the older Muslim and military fabric underneath the Renaissance building

Look at the carved wooden ceiling in the refectory, which is the thing people come for

Find out where the Camino de Uclés starts and how long it takes to walk

Alfonso VIII gave the castle at Uclés to the Order of Santiago in 1174, and it became the Caput Ordinis — the head of the order, its most important house anywhere. The present monastery was begun on 7 May 1529, under Charles I, starting with the Plateresque east wing, on a hill above the village with the older Muslim and military fabric underneath and around it. It gets called the Escorial of La Mancha. The Camino de Uclés, a pilgrimage route from the church of Santiago in Madrid, ends here.

Uclés: The Escorial of La Mancha

Sit in the theatre and find out which local family paid for it and what they had made their money from

Work out what lapis specularis was and why translucent gypsum was worth that much to Rome

Walk the amphitheatre and the forum, both finished by the end of Vespasian's reign

Go to one of the lapis specularis mines in the area and see where the sheets came out of the ground

Work out what happened to the town — the population simply moved three kilometres to Saelices, next to the spring

Pliny records that Segóbriga mined lapis specularis — translucent selenite gypsum, split into sheets and used as window glazing across the Roman world. It made the town rich enough that some local families put senators into Rome. Manius Octavius Novatus, son of a praefectus fabrum of the same name, paid for the theatre; his cognomen survives in the place name Noheda, where his family's villa was. By the end of Vespasian's reign the theatre and amphitheatre were finished and the town was fully integrated into the empire. After the reconquest the population moved three kilometres north to Saelices.

Segóbriga: The Town That Glazed Rome's Windows

Stand in the Plaza Mayor and work out that the stone under your feet came from the edge of the town

Go and look at the quarries, which supplied a great deal of Madrid as well as this square

Find out what a tinaja is and why making them was an industry here

Go to the Ulpiano Checa museum and find out who he was

Work out the reversal: the second town of the province in the 19th century, and what it is now

Colmenar de Oreja was, until well into the 19th century, the second most populous town in the province of Madrid after the capital itself — built on stone quarrying, the making of tinajas, wax, esparto, textiles and farming. Its Plaza Mayor is a large arcaded square of local stone, and the quarries that supplied it and much of Madrid are on the edge of the town. The painter Ulpiano Checa was born here and has a museum. Nine wineries work under the Vinos de Madrid designation, in the Arganda subzone.

Colmenar de Oreja: A Town Built of Its Own Quarry

Find the ducal palace where Ana de Mendoza spent her last years and died in 1592

Find out what happened between Ana de Mendoza and Teresa of Ávila, and why Teresa pulled every nun out of the town

Go into the collegiate church for the four tapestries — eleven metres by four, woven at Tournai, recording Asilah and Tangier in 1471

Work out what makes them unusual: the first tapestry series to narrate contemporary politics in this kind of detail

Walk the two quarters of the town, the old and the ducal, which were laid out separately

Ana de Mendoza, Princess of Éboli by her marriage to Philip II's favourite Ruy Gómez de Silva, was one of the most powerful women in Spain — she and her husband founded two Discalced Carmelite convents here, then fell out so badly with Teresa of Ávila that Teresa ordered every nun out of Pastrana and left her alone in them. Ana died here in 1592. The collegiate church holds four silk and wool tapestries averaging eleven metres by four, woven in the Paschier Grenier workshop at Tournai on the order of Afonso V of Portugal, recording his conquests of Asilah and Tangier in August 1471 — the first tapestry series to narrate contemporary political events in this kind of descriptive detail.

Pastrana: A Princess Under House Arrest

Work out the dating from the coats of arms — the third wife of 1472 is not on the building anywhere

Find where the design accommodates artillery, which was a new problem in the 1450s

Work out that this is a palace as much as a fortress, and where one becomes the other

Find out who Eugenia de Montijo was and why an empress of the French restored a castle in Cuenca

Go down to the collegiate church in the village, which Hanequín de Bruselas also worked on

Juan Pacheco, first Marquis of Villena, started this castle on the Cerro de San Cristóbal in 1455 and the work ran to about 1468 — you can date it from the heraldry, because his third wife, married in 1472, appears nowhere in it. Hanequín de Bruselas was the architect, and Juan Guas probably finished it. It was built as a fortress-palace and specifically adapted for the coming of artillery, which was a new problem at the time. Eugenia de Montijo, empress of the French, inherited the house of Villena and restored it.

Belmonte: A Castle Built for Artillery

Stand in the Plaza Mayor and work out why it is irregular — it grew round penned livestock rather than being designed

Look at the tiered wooden galleries and work out that they were built as balconies to watch animals from

Come when the square is sanded for a bullfight or a festival and see what it was always for

Find out that this square played the Spanish bullring in Around the World in Eighty Days, with much of the town as the crowd and Cantinflas as the matador

Climb to the castle ruins and the old church above the town for the view over the Tagus valley

Chinchón's Plaza Mayor is irregular rather than laid out, because it grew: livestock were penned around the houses so their owners could watch them from the balcony without going outside, and that is why the whole square is ringed with tiers of open wooden galleries on stone columns. It is protected as a Historic Ensemble. Several times a year the ground is sanded and the square becomes a bullring, which is what those balconies have always been used for, and the rest of the time it is where the town eats.

Chinchón: The Square That Is Still a Bullring

Go into the Casa de Dulcinea and work out what a 16th-century Manchegan house actually contained

Find the library of Don Quixote in over sixty languages and see which heads of state sent which

Read the chapter where Quixote and Sancho get lost in these streets at night, standing in them

Work out the oddity: a real village living with the identity of a character who was herself imagined by a character

Walk out into the vines and olives around it, which is what the Mancha actually looks like

Cervantes gave Don Quixote's imagined lady a home village, and it is this one — Dulcinea del Toboso, in a place that already existed and has been living with it ever since. The town has a Casa de Dulcinea, a 16th-century Manchegan house furnished as she might have kept it, and a library of Don Quixote in more than sixty languages, many of them presented by heads of state. There is also a chapter in the book where Quixote and Sancho blunder about these streets at night unable to find the house, which is worth reading in situ.

El Toboso: Dulcinea's Village

Walk the Teneguía cone, which erupted for twenty-four days from 26 October 1971

Go on to San Antonio, which erupted in 1677, and find the Roque de Teneguía its lava wrapped round

Walk down to the Salinas de Fuencaliente and the two lighthouses at the southern point

Work out the colour contrast: black lava, white salt and the Atlantic, all in one frame

Find the petroglyphs on the Roque de Teneguía, cut by the aboriginal population long before either eruption

The southern tip of La Palma is where the island is still actively growing. San Antonio erupted in 1677 and Teneguía began on 26 October 1971 and stopped on 18 November — twenty-four days, the shortest of the eight eruptions La Palma has recorded since 1430, and the most recent anywhere in Spain until Tajogaite in 2021. The cone is 431 metres and takes its name from the Roque de Teneguía beside it, a phonolite dome ringed by the 1677 lava that carries aboriginal petroglyphs. Below them the Salinas de Fuencaliente work seawater into salt beside two lighthouses, one of 1903 and one modern, with black lava on one side and white salt pans on the other. The vines here grow in volcanic ash and make Malvasía.

Fuencaliente: Volcanoes, Salt and the Southern Tip

Float in the Laguna Rosa and work out that you cannot sink in water this saline

Work out what makes it pink — halophilic bacteria and algae in water nothing else survives in

Find out what happened between 1389 and 1482 when the crown tried to make it a fishery

Go across to the La Mata lagoon, which is green rather than pink, and work out why

Look for flamingos, which feed on the same organisms that make the water pink

The lagoons of La Mata and Torrevieja have been worked for salt since at least 1321, when the crown gave Torrevieja's to the city of Orihuela, and they are still one of the largest salt operations in Europe. The Torrevieja lagoon is bright pink, from halophilic bacteria and algae living in water far too saline for anything else, and the salinity is high enough that you float in it the way you do in the Dead Sea. In 1389 the crown tried to turn it into a fishery and gave up in 1482 when it became clear no fish would enter water that salty.