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

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

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

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

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

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

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

Walk in through the successive gates strung along the neck and work out that there is no other way in

Look down at the Júcar and work out how nearly the loop closes

Work out why the place was called impregnable, and that Alfonso VIII still took it in 1184

Go into the 8th-century Muslim castle at the end of the spur, a parador since 1966

Count the churches in a village of a few hundred people and work out what that implies

The Júcar loops almost completely round the promontory Alarcón stands on, which made the place effectively impregnable — the castle is Muslim work of the 8th century and Alfonso VIII took it in 1184. The way in is still through successive gates strung along the neck of the meander. The castle at the point of the spur opened as a parador in 1966 and is now what the town largely lives on. The village inside the walls has a few hundred people and four churches, which tells you what size it used to be.

Alarcón: A Fortress in a River Loop

Walk the circuit and work out that every shape in it was cut by water out of a seabed

Work out the sequence: Tethys seafloor 90 million years ago, lifted by the alpine orogeny, then karst weathering ever since

Find the fossils in the rock, which are the direct evidence of what this was

Work out why it was protected as early as 11 June 1929, which is very early for a Spanish natural site

Go on into the wider Serranía de Cuenca and find the Ventano del Diablo over the Júcar gorge

Ninety million years ago this was the floor of the Tethys sea. The alpine orogeny at the end of the Cretaceous lifted it out of the water, and karst weathering since has cut the limestone into freestanding blocks, mushrooms, corridors and arches at 1,500 metres among pine forest near Valdecabras. It was declared a Natural Site of National Interest on 11 June 1929 and now sits inside the Serranía de Cuenca natural park. The land is private and there is a modest entry charge, which is worth knowing before you drive out.