Cycling the Paradors of Extremadura

South West of Madrid (1 hr 40min by train), Oropesa is the gateway town to your historical cycling tour. Oropesa is one of the oldest inhabited sites in Spain, dating back to 1761 BC when the legend says that Hercules founded the town. For centuries, Oropesa has served as refuge for monks, nobility and travelers.

After your bike fitting, it’s gentle beginnings across the flatlands of Extremadura. Cycling northwest towards the Gredos Mountains, you'll first ride on the flat plains known as “dehesa”, with grassland and some holy oak trees. Then you will have more hills and terraced terrain, riding through several villages where you can eat or buy a picnic. Mediterranean forests line your route on the approach to Jarandilla de la Vera. Once home to Emperor Charles V, Parador Jarandilla is a 15th-century castle nestled amongst orange trees and almond groves. 

Total ascent/descent: 615m/450m

Today’s ride follows the ancient Roman ‘Ruta de la Plata’ (silver route) to the market town of Plasencia. Today´s ride is all in tarmac and you have a mix of roads. You'll continue riding through the foothills of the mountain range towards Plasencia. There are several climbs but none of them are too long or steep. You start on the main road to Plasencia and just before Tejada del Tiétar the route goes off into more secondary roads with wonderful views of the plains of Extremadura. You'll then rejoin the main road for the final 8km. Plasencia is a fantastic place to explore. Retaining much of its 12th-century city wall along with 68 towers, the double cathedral complex and Moorish ruins are a testimony to the rich Islamic and Christian history. Your Parador tonight is the delightfully converted 15th century Santo Domingo Monastery.  

Total ascent/descent: 715m/980m

A region famed for raising the fierce ‘El Toro’ and black ‘Iberico’ pig, Monfrague National Park is also a bird lover’s paradise. Today´s ride takes you into the National Park of Monfragüe, heading South away from the mountain range. There is a steep climb at the beginning to leave the city as it is situated in the valley of the River Jerte but then you will be generally descending before you reach two more climbs at the end in the natural park close to your hotel.The rocky outcrops are populated by Egyptian, Eurasian Black and Griffon Vultures. Spending the evening in lovingly restored Casa Rural, your hosts will be happy to provide further guidance about the rich flora and fauna in this region.

Total ascent/descent: 480m/520m

A peaceful pine-scented route takes you from the rich bio-diversity of Monfrague to the conquistador’s town of Trujillo. Today´s ride is relatively flat and easy. It is good that it is only 48 km so that you can probably get to your hotel before lunch since there is a lot to see, do and many places to eat in Trujillo. The surrounding landscape is grassland dotted with cork and holly oak trees and you will probably see bulls, sheep and black pigs scattered in the big properties. Once the Santa Clara Convent, the restored renaissance arches preserved the peaceful ambience of Parador Trujillo. With two nights here, there are plenty of opportunities to soak up your serene surroundings from the comfort of the poolside. Home to conquistadors; Fransico Pizarro, Diego Parades and Hernan Cortes, Trujillo's labyrinth of medieval streets, churches and historic houses sprawl up the hillside. 

Total ascent/descent: 510m/300m

Enjoy a scenic loop ride from one of Spain's most significant cultural and historic towns, taking you through the town and to the mountains nearby. The circular route is one of the longer routes of the tour and it does have some important climbs but it does take you to the beautiful hills of Sierra de las Villuercas, a wild and isolated part of Extremadura. The land is managed very little and is mostly used as hunting grounds. You are likely to see a variety of birds of prey and small and large mammals living in this typical Mediterranean oak woodland and shrubland. 

Total ascent/descent: 555m/520m 

Alternatively, you may wish to opt for a rest day here, and explore Trujillo on foot.

Cycling through sleepy villages, country lands soon give way to the UNESCO town of Caceres. Today's ride is relatively easy since it is mostly flat except for one point in the middle of the ride where you go down to a river and then have to climb up the valley. A crowded skyline of turrets, storks’ nests and church spires, Caceres is a feast of sightseeing which will take you back to the golden age of Spanish Explorers, Moorish rule and across the ancient route ‘Via Delapidata’, used by pilgrims heading for Santiago de Compostela. Your final Parador this evening is an exquisitely preserved 15th century Renaissance palace.

Total ascent/descent: 310m/400m

Depending on your travel plans, you may wish to explore Caceres further or take a direct train service to Madrid (3 hrs).