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Consuegra's windmills and castle

Castilla–La Mancha self-drive

9-day tailor-made self-drive from £1,160 pp incl. flights


Short description

Knit together stays in centuries-old castles with a road trip through medieval Spain


  • Explore medieval towns and windmill villages
  • Stay in historic castles and converted monasteries
  • Link it all with super-scenic drives
  • Rest up in a spa retreat
  • Enjoy time to explore at your leisure

In Brief

  • 1 Night Sigüenza
  • 1 Night Cuenca
  • 1 Night Albacete
  • 1 Night Almagro
  • 2 Nights Toledo
  • 2 Nights Oropesa


Recommended for:
Food & wine | History & culture | Self-drive

Sweeping between vineyards, olive groves and windmill-dotted plains, this scenic road trip links together all the highlights of Spain’s lesser-visited central region. You’ll pause at walled villages and medieval towns where Don Quixote’s history lives on in knight’s forts and cobblestone-charm. What’s more, you’ll stay right among it all, with nights spent in centuries-old castles and stately monasteries. Indeed, this itinerary offers plenty of time to explore at your leisure, whether you want to relax with tapas fineries or examine some of Spain’s most spectacular cathedrals in further details.

Day by day itinerary

Day 1

After enjoying your complimentary VIP lounge access, you’ll fly out to Madrid. After picking up your hire car at the airport, you might want to check out its neoclassical cathedral and masterpiece-stuffed art galleries, before heading out. Watching as the city limits fade into shrub-covered plains, your goal is Sigüenza. This sleepy town’s quiet, riverside setting belies its castle, cathedral and twisting medieval laneways that branch out from a 16th-century plaza. Forgive the umlaut, this is distinctly Spanish. And, you’ll stay right in its iconic castle, whose imposing battlements house traditional Castilian furnishings. It’s even built atop a Roman settlement.

Stay: Parador de Sigüenza (Superior)

Day 2

After the first of your indulgent breakfasts, you’ll drive out through sweeping farmlands, kissing the Tagus River before arriving at Cuenca. Here, you’ll stay in a stately 16th-century monastery. All terracotta tiling and dark-wood furnishings, it’s the perfect introduction to the city’s UNESCO-listed charms. Indeed, medieval Cuenca is perched atop a rocky promontory, watched over by an imposing castle and lined with its famous “Hanging Houses”, whose timber balconies perch precipitously over the cliff edge. Then, back in the centre, you’ll wander between Baroque churches, a Gothic cathedral and a royal monastery. There are also some spectacular natural rock formations nearby.

Stay: Parador de Cuenca (Superior)

Meals: B

Day 3

You’ll sweep on south today, through fertile plains, to arrive at your accommodation – a traditional country house where long, exposed-beam corridors spill onto sculpted grounds and a nine-hole golf course. Just nearby, you’ll find the Castle of Chinchilla, whose 15th-century tumble offers some of the finest views over the region’s rolling prairies. And, alongside church villages and the Alcaraz y Segura Mountains, there’s also Albacete itself. As the province’s largest city, it offers a fine Modernista shopping arcade, a superb archaeological museum and a lively tapas scene.

Stay: Parador de Albacete (Superior)

Meals: B

Day 4

After breakfast, a short drive will see you on to Almagro, a spectacular whitewashed town that rises above the La Macha plains. And, your accommodation here is its eponymous parador. Housed in a 16th-century monastery, it’s a masterpiece of interior courtyards, bright galleries and beautiful woodwork. It’s also just five minutes from the town’s main plaza. From here, you’ll wander between centuries of history, kept alive today in museums, an open-air theatre and a fantastic collection of palaces and stately homes.

Stay: Parador de Almagro (Superior)

Days 5-6

As you start to loop back towards Madrid, you’ll arrive at Toledo. Like Almargo before, its hilltop position provides a commanding overlook, with its walled old city cloaking a medieval history that draws on Arabic, Jewish and Christian tradition. And, you’ll stay – for the next two nights – right among it all in an 18th-century townhouse, with grand mosques, synagogues and one of the country’s finest Gothic cathedrals all on your doorstep. It’s all set to gorgeous ravine and river views.

Stay: Parador de Toledo (Superior)

Meals: B

Days 7-8

Your final stop is Oropesa, where you’ll end in style with a two-night stay in a 14th-century castle. It’s the original parador, grand in its colonnaded courtyards and arcade-dotted keep. While it’s the town’s icon, there’s plenty more with Oropesa’s walls, from noble mansions to Renaissance churches and a 16th-century Jesuit school. Be sure to also get yourself to the main square, where bars and restaurants spill out onto the pavement, offering excellent people-watching opportunities.

Stay: Parador de Oropesa (Superior)

Meals: B

Day 9
Depart for UK

After a final breakfast, you’ll drive back to Madrid where you’ll drop off your hire car and board your flight home.

Meals: B



Any element of this itinerary can be adjusted to suit your needs. Just contact us to find out more.

Accommodation rating: Superior

9-day tailor-made self-drive
from £1,160 pp incl. flights


Apr / Oct

from £1,160 pp. incl. flights

May - Sep

from £1,330 pp. incl. flights


  • Complimentary UK airport departure lounge access
  • Return flights between UK and Madrid
  • 9 days car hire in an Economy vehicle (size upgrades available on request)
  • 8 nights accommodation in historic Parador accommodation on a BB basis

Supplements may apply to some properties for Friday and Saturday night stays

Terms & Conditions

Prices are per person based on two people sharing a twin/double room; prices are subject to availability and possible change; normal booking conditions apply.

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At Wexas, we specialise in bespoke travel experiences. Our itineraries are just samples of what we can arrange, and can be changed depending on your precise needs, finances and ideas by our experienced destination specialists.

Contact one of our consultants on 020 7664 2264 to discuss how we can tailor your holiday.

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