8 Days & 7 Nights

4.4

Cycling the Paradors of Extremadura

Cycle the historic lands of Conquistador Explorers
Stay in lovingly restored medieval palaces, convents and historic hotels
Ride across the ancient Roman ‘Ruta de la Plata’
Visit Trujillo Castle, home of the Casterly Rock in Game of Thrones
Explore the UNESCO city of Caceres

Cycle the rise and fall of Spain's historic 'Golden Era'. Spend each night in historic 4-star hotels and Parador hotels, lovingly restored medieval palaces, castles and convents. Extremadura, Land of Conquistador explorers, boasts a wealth of perfectly preserved medieval towns, taking you back in time to the region's 16th-century heyday. From the historic heart of Oropesa, you'll ride across rich agricultural lands and via sections of the ancient' Ruta de la Plata' to the 12th-century walled market town and Moorish ruins of Plasencia. Cycle through the wonderful sounds of birdlife in Monfrague National Park, leading to the architectural splendors of Trujillo. Home to explorer Francisco Pizarro and Trujillo Castle, the location used for Game of Thrones Casterly Rock, you will get to spend two nights here to explore this town. The final section of the trip ends in the UNESCO town of Caceres, staying in a Renaissance palace in the heart of the old quarter. This is a lovely way to complete this explorer's adventure.

From £1,159.00

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Itinerary

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Day 1 Arrive Oropesa

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.

Overnight Oropesa

Accommodation

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Casa Platon de Paramo | 4 Star | Hotel

Used for 2025 bookings

With its halls, galleries, lush patios and historical elements, Casa Platon de Paramo boasts charm and character. The house dates back to 1800 and retains all the structure and layout of the period with thick walls, 19th century wrought iron railings, numerous 16th century plasterwork, classical doors, antique plates from the 18th to the 20th century, medieval stone shields and capitals, cipos (Arab funerary monuments) from the 11th century and, most valuable, the beautiful interior doorway of the Torrijos Palace, belonging to the Dukes of Sesa and Altamira, which was demolished in 1903.

Parador de Oropesa | 4 Star | Hotel

Due to recent flooding in the area, this Parador is undergoing renovations and will remain closed until December 2026.

Once the ancestral home of the Alvarez De Toledo family, the Oropesa was the first converted Parador in this historically, luxurious, unique hotel collection. From you Parador it’s easy to explore the historic quarter of Oropresa or relax in the peaceful grounds and enjoy views across to the Gredos Mountains from the swimming pool. The restaurant, with views of the impressive Oropesa Castle and the Sierra de Gredos, serves regional produce and specialities.

Day 2 Oropesa to Jarandilla de la Vera 42 miles / 68 km

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

Overnight Jarandilla de la Vera

Accommodation

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Hotel Ruta Imperial | 4 Star | Hotel

Hotel used for bookings till mid-September 2025

Hotel Ruta Imperial offers a relaxing retreat with a seasonal outdoor swimming pool, peaceful gardens, a shared lounge, and a scenic terrace. Guests can enjoy regional cuisine at the on-site restaurant, unwind with a drink at the bar, or soak in the hot tub after a day of exploring. Surrounded by nature, the hotel combines comfort, charm, and attentive service for a memorable stay.

Parador Jarandilla de la Vera | 4 Star | Hotel

This Parador is temporarily closed for renovations until mid-September 2025.

Located between gorges, woods of chestnut trees and oak groves, the natural landscapes surrounding Parador Jarandilla de la Vera reaffirm the richness of the historical, majestic surroundings, with the parador playing host to guests including Emperor Charles V, since the 14th century. From the poolside, peaceful gardens with olive and orange trees extend to the Tietar River. Enjoy the parador's restaurant, serving a varied selection of Extremaduran cuisine.

Day 3 Jarandilla de la Vera to Plasencia 42 miles / 67.5 km

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

Overnight Plasencia

Accommodation

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Parador de Plasencia | Hotel

Located on an ancient pilgrimage route this 15th century monastery greets you with thick stone walls, vaulted ceilings and Gothic interior.

Day 4 Plasencia to Monfrague 27 miles / 44.5 km

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

Overnight Monfragüe

Accommodation

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Palacio Viejo Casa Rural | Country House

Dating back 200 years, nestled in 600ha of farmland, Placio Viejo is a lovingly restored traditional country house - a perfect place to absorb the peaceful country life of Monfrague.

Hospedería Parque de Monfragüe | 4 Star | Hotel

Hospedería Parque de Monfragüe is located at the entrance to Monfragüe National Park, a site of unique wildlife and biodiversity.

It is the perfect location to explore the park and unwind surrounded by nature.

This modern hotel has a large swimming pool and balconies. Relax by visiting the spa, or keep fit in the gym.

Day 5 Monfrague to Trujillo 30 miles / 48 km

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

Overnight Trujillo

Accommodation

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Parador de Trujillo | 4 Star | Hotel

Occupying the former convent of Santa Clara this Parador boasts two beautiful cloisters, which retain the peaceful ambiance and tranquillity of this historic building.

Day 6 Circular ride from Trujillo; optional rest day 39 miles / 62.5 km

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.

Overnight Trujillo

Accommodation

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Parador de Trujillo | 4 Star | Hotel

Occupying the former convent of Santa Clara this Parador boasts two beautiful cloisters, which retain the peaceful ambiance and tranquillity of this historic building.

Day 7 Trujillo to Caceres 34 miles / 55 km

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

Overnight Cáceres‎

Accommodation

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Parador de Cáceres | 4 Star | Hotel

Parador de Cáceres is a Renaissance palace in the heart of the city's old quarter, which has been declared a World Heritage Site. You will fall in love with the Parador's elegance and exquisite refurbishment, enjoy pleasant chats in its function rooms and meals in the cozy garden.

Day 8 Onward Travel

THIS TRIP'S CARBON SCORE

This trip has a carbon score of 4kg per person per night, meaning it’s one of our best trips! For comparison, a carbon count of 4kg is equivalent to 2.5 avocados. Here at Macs, we pride ourselves on being a responsible travel company and continue to adopt, develop and innovate ways to positively impact the environment. Find out more information on how we've carbon counted our trips.

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Other Information

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Is it for me?

Graded moderate, you’ll be earning each night of luxury in historic 4-star hotels, country houses and Parador hotels. Cycling days are broken up with picturesque rest-stops, village tapas bar and a wealth of Spanish history. Daily distance usually cover around 44km—86km and include some sections of hillier terrain. This is a perfect trip for active travellers that enjoy an evening of comfort and history after a day in the saddle.

Trip Type:

Slower Adventures | Where walking and cycling meet easy-going exploring, our Slower Adventures are the perfect combination. Most days are filled with picturesque journeys with some free time to dive into the destination and experience the people, local food and culture as you go.

Activity:

Leisure Cycling | Leisure Cycling

This trip is suitable for:

Solo Travellers

The minimum age for this tour is: 16 Years

Ideal if you have an interest in:

Off the Beaten Track

Grade & Terrain

The routes on this cycling trip are graded Moderate. Occasionally you may encounter a few moderate slopes, however, the ascent is not too difficult or prolonged. You will cycle principally on quiet country lanes, cycle lanes, and some busier roads when approaching towns. Please always be mindful of other road users. The surface is mostly tarmac throughout this tour, though there may be very short sections where the condition is not as good, making it harder work.

Daily distance usually cover around 44km—68km and include some sections of hillier terrain, as you cycle through the foothills of the mountains of the "La Vera" region. Cycling days are broken up with picturesque rest-stops, village tapas bars and a wealth of Spanish history. Your daily routes outline towns and villages where you can refuel with water and suggest local places where you will be able to have lunch or a snack. This is a perfect trip for active travellers that enjoy an evening of comfort and history after a day in the saddle.

Accommodation & Meals

Accommodation Information

During this tour you will overnight at 4-star parador hotels, 4-star hotels and country house hotels. Paradors in Spain are a network of restored castles, monasteries, convents, fortresses, manor houses and palaces. They hold historical and cultural value.

Important Update on Accommodation:

Please note that two of the Paradors on our itinerary are currently closed for renovations. However, we’ve secured exceptional alternatives that promise comfort, charm, and a memorable experience.

Day 1 – Parador de Oropesa:
Due to recent flooding in the area, this historic Parador is undergoing renovations and will remain closed until December 2026. In its place, we’ll be staying at Casa Platón de Páramo, a beautifully restored hotel nestled in the heart of Oropesa’s historic centre. This elegant property offers a perfect blend of glamour and heritage, ensuring a delightful stay.

Day 2 – Parador de Jarandilla de la Vera:
This Parador is temporarily closed for renovations until mid-September 2025. As an alternative, we’re pleased to offer accommodation at the Ruta Imperial, a 4-star gem set in stunning grounds with serene forest views. Known for its exceptional service and peaceful ambiance, it’s a wonderful retreat after a day of exploration.

Single Rooms

If you require single rooms within your party we would be happy to accommodate you although there is a single room supplement payable.

Solo Cyclists

This tour is suitable for solo cyclists for a supplement.

Meals

Breakfast is included each morning. Breakfast is a leisurely affair and adequate time should be allocated. Lunch and dinner are not included. Most accommodations are happy to provide a packed lunch - this should be requested on arrival. Dinner is available either at your accommodation or nearby bars, cafes and restaurants.

Navigation What's Included

Included

Parador hotels, 4-star hotels and country house hotels
All breakfasts
Baggage transfers
Detailed trip info and mapped tracks, via the Macs App
24/7 Emergency telephone support from our UK & US offices

Excluded

Travel to Oropesa / from Caceres
Bike hire/E-bike hire
Lunches, dinners, snacks and drinks
Personal equipment
Travel insurance (required)

Extras

Additional nights along the route
Upgrade you meal plan to half board
Bike hire/ E-bike hire

When to go Travel & Transfers Info & FAQ

General Information

The distances and ascents/descents are approximations of the recommended routes. Please be prepared by packing all the necessary items, for example, proper rain gear, sun hat, sunscreen. Your information pack has detailed advice and a kit list on what to take. This includes good waterproof gear, sports shoes, and lots of other useful bits and bobs.

Equipment

Bike & E-Bike Hire

Kross Trans Alp 24 speed touring bikes are available for hire. Rental bikes come equipped with a basic repair kit, pump and helmet (though we recommend using your own). Male and female frames are available. E-bikes are also available on this trip which offers a boost on the hills are the legs need a little help pedalling.

If you’d like to hire a bike, please let us know your height and frame size you currently ride.

If you would prefer to bring your own bicycle please ensure it is thoroughly serviced and is an appropriate bike for this trip such as a Giant Argento, Scott Sub, Trek 7200 or similar.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.