Castilla–La Mancha self-drive

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)

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)

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)

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)

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)

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)

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