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bici  The Land of Conquistadors
   from Parador to Parador

moderado plusDifficulty: Moderate+
  • Difficulty: Moderate+
  • Category: Cycling, self-guided
  • Duration: 6 nights, 7 days
  • Recommended time of year: 1st March-31st June and 1st Sept-30th November

Self-guided, moderate+ level cycling tour along the Land of Conquistadors from Parador to Parador.

  • Luxurious Parador Hotels.
  • Historic towns of Oropesa, Plasencia, Trujillo and Cáceres (World heritage city).
  • Self-guided, cycling holiday along quiet country lanes.
  • Cycling across Monfrague National Park, very rich in birdlife.
  • Excellent hotels with swimming pools.
  • Luggage transfers included.

This tour is a great way to discover a magnificent area of central Spain, Extremadura, while enjoying your stay in the Parador Hotels of this region. Paradors are a semi Estate owned chain of high end hotels that offer a superb service. Their uniqueness lies in the fact that they are all placed in renovated, historic buildings such as palaces, castles or convents.

Extremadura is the land of the “Conquistadores”, the men that pioneered the exploration of the Americas as the Spanish Empire expanded. The magnificent wealth generated by its people can be seen in towns like Trujillo and Caceres, in the Palaces that where built by the pioneers that came back.

This region is also a privileged land with a great amount of water and gracing land. The low altitude and southern aspects makes the winters mild in contrast with the cold winters of the northern plateau. Throughout many centuries herds of sheep and cattle have been brought to Extremadura in the winter in search of fresh pastures and a benign climate and then returned back in the summer to the central and northern mountains.

The route starts in Oropesa that is actually in the province of Toledo and then takes us North to the dramatic Mountains of Gredos to then follow the foothills of the mountains on the “La Vera” region that is a beautiful, fertile land, full of terraced olive groves and fig, cherry and fruit trees. The mountains bring much needed water to Extremadura as small rivers descend from its slopes and appreciate an area that is still very alive and has an active agriculture.
After La Vera you visit the town of Plasencia on the side of the river Jerte to then head South towards Trujillo and Caceres on the flat grazing land. Before visiting these two magnificent historic towns you will cross the National Park of Monfragüe famous for its bird life.


Which airport should I fly to? Madrid International Airport.
How do I get to the Starting Point? By train from Madrid Atocha train Station to Oropesa.
How do I get back to Madrid Airport? By train from Caceres to Madrid Atocha station.

Day 1: Arrival to Oropesa

Individual arrival to Oropesa, which can be easily reached by train from Madrid. (1hr, 40 min).

Day 2: Oropesa to Jarandilla de la Vera

Your rental bike you will be delivered after which, your cycling adventure begins!  Through typical Mediterranean woodlands, the route leads to the foothills of the Gredos Mountains, whose granite cliffs are a perfect backdrop for the day's route providing stunning views. Jarandilla de la Vera, final destination of the day, showcases architectural wonders such as the churches of San Agustin and Ntra. Senora de la Torre. Your stay tonight is in a restored castle that once hosted Emperor Charles V for several months!.
34 or 41 miles (55 or 67 km)

Day 3: Jarandilla de la Vera to Plasencia

This day's cycling is through peaceful countryside to the walled market town of Plasencia. Nestled on the bank of the Jerte River, Plasencia has experienced many benefits (and downfalls) from its strategic location on the Ruta de la Plata- the Silver Route. Palaces, ancestral homes, and significant religious buildings make up the architecture of this beautiful city.
36 or 42 miles (59 or 69 km)

Day 4: Plasencia to Monfragüe National Park

Cycling south towards the Tajo River, you will reach the National Park of Monfrague, a well-known place for all bird watching enthusiasts. The landscape here is a unique juxtaposition of farming land and cork and oak trees. The farms in this area are dedicated to raising wild bulls and the famous black "iberico" pig.
21 miles (33km)

Day 5: Monfragüe to Trujillo

Another cycle through mediterranean woodland to reach Trujillo. Trujillo is one of the area’s most important historic and cultural towns and is certainly one of Spain's finest gems. The walled hilltop town, which overlooks the expansive countryside, dates back to 600 BC and is famed for its strategic involvement in the discovery of the Americas.

Several of Spain's most famous conquistadors such as Hernan Cortes who conquered the Aztec empire, Francisco Pizarro who conquered the Inca Empire, and Diego Parades, all called this region home. On their return from the Americas to Trujillo, these Conquistadors built magnificent residences to celebrate their newfound wealth. The legacy of the conquest can be seen in much of Trujillo’s perfectly preserved architecture and the impressive bronze statue of Francisco Pizzaro mounted on his horse, which dominates the town’s main square.
31 miles (49 km)

Day 6: Trujillo to Caceres

The scenery of the last bike ride is a beautiful mix of small villages and stunning landscapes. Reaching the monumental city of Caceres, you will be transported back in time as the architecture reflects a blend of Roman, Islamic, Northern Gothic and Italian Renaissance influences. Be sure to explore the narrow cobbled streets as they twist and climb among ancient stonewalls lined with palaces and mansions!.
34 miles (55 km)

Day 7: Departure

Departure from Caceres, you can extend your journey or take a train back to Madrid.



Day 1 Parador Nacional Oropesa

Your hotel is a 15th Century Palace and Castle. The stately home of the Álvarez de Toledo, Counts of Oropesa, once the home of soldiers, clergy and noblemen, enjoys exceptional views of the Sierra de Gredos. The historic value of the “Torre del Homenaje”, a tower attached to the Parador, the columns of the courtyard, and the pool with outstanding views over the plains of Campo Arañuelo, make this into a very attractive hotel.

Day 2 Parador Nacional Jarandilla

Palace-castle from the 14th century. It lies sheltered in the middle of the Vera and Tiétar valleys, between gorges filled with water, woods of chestnut trees and oak groves and stunningly beautiful natural landscapes that reaffirm the richness of their historical, majestic surroundings. For months it played host to an illustrious guest - Emperor Carlos V. From the exterior, the towers, courtyard, ‘patio de armas’ courtyard and its excellent swimming pool contrast with the olive and orange trees. Inside, you will find a relaxing and intimate atmosphere.

Day 3 Parador Nacional Plasencia

The Parador is a historic building just inside the walls of the city. The hotel is in the former convent of Sto. Domingo, founded by the Zúñiga family in the mid-15th century, in the Gothic style inside and in part of the exterior. Strategically located in the historic centre of Plasencia, this is the ideal place to explore the architectural beauty of this singular city and the beautiful landscape around it.

Day 4 Hotel Palacio Viejo de las Corchuelas

Beautiful 600 ha farm. It houses a charming country house in a carefully restored traditional building dating back 200 years. Due to its privileged location, at the foot of Las Corchuelas Mountain Range- the backbone of Monfragüe´s National Park-, and surrounded by cork and holm oads, it is a unique and incomparable destination to enjoy peace and unadulterated nature. 

Day 5 Parador Nacional Trujillo

In the historic city of Trujillo, birthplace of explorers, this lovely hotel occupies the former convent of Santa Clara FROM THE 16TH century, with its atmosphere of peace and tranquillity. Outstanding features of the interior are two beautiful cloisters: one with Renaissance arches and columns, the other bringing light into the building. Ideal for relaxation and leisure, the hotel has monastic style rooms and details, spacious, quiet and pleasant lounges, noble bedrooms with wooden furniture and a bar-café next to the light-filled cloister of the Parador. One of the most impressive spaces is the breakfast room since it is a beautifully decorated chapel.

Day 6 Parador Nacional Cáceres

The Parador de Cáceres represents the harmonious union of the palaces of the marquises of Torreorgaz and the so-called Ovando Mogollón, Perero y Paredes House, both dating from the 14th century. The interior of the building boasts all the elegance, quality and comfort of a historic structure adapted to suit the needs of today's guests, especially the restaurant and outdoor areas, café and guest lounge. This last room is a particularly pleasant spot to meet and chat. It is conveniently situated in the old historic centre in a pedestrian area.


Our hire bikes and equipment:

A bicycle specialist will deliver your hire bike and adjust it to your specifications. We provide you with fully equipped touring bicycles. Remember that we carry your luggage between hotels so you can travel light.


GIANT ARGENTO or equivalent:
  • Hybrid bikes
  • Larger, confort seat
  • Front suspensión
  • Adjustable handle bars
  • 29 inch hibrid tires
  • 24 gears
  • Bicycle stand
  • Bottle holder
  • Mudguards
  • Bike Computer (odometer)
  • V-breaks

Other equipment provided:

  • Rear panniers
  • Map carrier
  • Helmet
  • Pump
  • Puncture repair kit
  • Multitool set
  • Bike lock


  • Price: 886€ per person
  • Single room supplement: 157€
  • Solo Traveller supplement: 289€
  • Half board / dinners (wine not incl.): 150€
  • Bike hire: 100€
  • Electric Bike hire: 150€
  • GPS rental (one per group): 15€
What´s included?
  • 6 nights’ accommodation at Paradors 4 **** and one night at charming rural hotel.
  • 6 breakfasts.
  • Luggage transfers between hotels.
  • Detailed maps with your trail clearly marked.
  • Itinerary description, full of recommendations for things to do and places to visit, advice and suggestions and information about your accommodation, etc.
  • Emergency support.
  • Activity insurance.

Using the tool below you can calculate the final price of your trip. PLEASE, BEFORE YOU BOOK, CONSULT AVAILABILITY.
Select an option

Cycling The Land of Conquistadors

Number of travelers

Single Supplement

Single room supplement: 157€

Half Board

Half Board (per person): 150€

Bicycle rental

Bicycle Rental (per bike): 100€

Electric Bike Hire

Electric bike rental (per bike): 150€

GPS rental

GPS rental (one per group): 15€

Extra night

Extra night in Madrid (per double or twin room): Price on asking.

Extra night

Extra night in Madrid (price per single room): Price on asking.

interroacion Difficulty



  • EASY: The route is almost exclusively through valleys and along rivers with no significant ascents.



  • EASY/MODERATE: Predominantly flat route with a few small ascents each day.



  • MODERATE: Undulating / hilly terrain with perhaps three ascents per day.


moderado plus

  • MODERATE+: Longer distances and hilly terrain, with perhaps four ascents per day.



Theresa Khairallah
We thoroughly enjoyed the ride and were quite happy to do our own thing. The extremaduran countryside is beautiful and the Semana Santa processions were impressive.

All the Paradors were stunning.
Theresa Khairallah, Easter 2014.

Ged and Audrey Bell
We are now in Madrid, for a few days after our fantastic trip with your company. Audrey and I wish to compliment you on a very professional and well-managed service. From the minute that we were picked up at madrid airport by Guzman, to the morning that we checked out of the Caceres Parador, everything was organised for us, and all we had to do was pedal!
Harry was also very helpful when he handed over the bikes and equipment at Oropesa. He also seemed to be impressed with the pace of two ‘more mature’ cyclists!
We will definitely recommend your services to our friends, family and colleagues. I will also be posting very complimentary reviews on Facebook and trip advisor.
We will also be in contact soon to organise future trips with away from the crowds.
I must compliment you on the quality of the maps, road book, hotels,
restaurant/cafe recommendations, bike quality and hotel choices. You should be very proud of the excellent business you manage. As for the routes, the national park was one of the most spectacular places we have ver visited, and we have been to many places around the world.

Julia and Neil Edmunds
Overall we thoroughly enjoyed the holiday – in fact I loved it, even the hard bits. We were incredibly lucky with the weather. All the Paradors were excellent. The directions were mostly good and the bikes were fine. Some feedback which I hope will be constructive:
There was one night where we didn’t eat at the Parador. If I had known this was likely I would have been able to tell you in advance what my dietary requirements are – I am a vegetarian plus I don’t eat eggs and this did cause a problem.
Some of the directions weren’t entirely clear and some of the distances were incorrect e.g. on day 2 we had to retrace our steps because we had overshot the turning by a couple of miles and this was uphill.

(N.E.: Since then, we’ve carried out a full revision of the route and amended errors.)
However an anecdote from the same day: We had just finished the detour in the national park; Neil had arrrived at the top of a hill and was waiting for me. We stopped to catch our breath and a farmer called over and introduced himself. He said his name was Michael. I think he was quite impressed about where we had come from and where we were going to. He invited up to fill up our water bottles, and to help ourselves to cherries and lemons from his orchards!
I would love to go on a similar holiday again some day.
Julia and Neil Edmunds, May 2014.

Diane and Tim Morris
We had to unexpectedly cut short our trip cycling through Extremadura and can not thank Jaime and Agustín enough for suggesting and making various arrangements to ensure we comfortably continued quickly onto Madrid. Throughout our trip, the attention to detail on the maps, scenic cycling and the comfort of the paradores was excellent, gracias!

See you again

Inge Bratley
we had a wonderful time, the paradores were fabulous places, your maps and info pack excellent, the bikes were great and your back up team very good and friendly. So all was perfect.

We did cut down on some of the distances for several reasons. It would have been a pity to spend all day in the saddle and not have the time for a relaxing afternoon exploring the towns we stayed in, have a swim etc. We managed to do all that so had a perfect combination of cycling, exploring and relaxing. The first day was quite difficult for us though as I had anticipated. Although we were taken for 20 km, by the time we had sorted out the bikes etc. it was 10 o’clock, far too late for a hot day. We got to the next parador at 3.30 pm having to have so many stops in the afternoon to try and cool down. But all in all we had a fantastic time and enjoyed it very much. So thank you for organizing such a wonderful trip. Will be looking at your website again, maybe try something else another time.
Thanks again
Kind regards
Inge Bratley, Cornwall, UK

Antonia Lanigan
Our overall impression of Senderos Y Pueblos was excellent, as everything was very well organised: our bags arrived safely and promptly everyday; the hotels were expecting us and accommodated our bikes, gear etc. and the maps and bikes were of a high standard. We loved Extremadura, the history, the landscape and the food all contributed to a memorable holiday.

Charlotte Taylor‎

We are now home after a fabulous holiday. We received great onsite support from Christine though the trailer the taxi man used to transport our bikes from the farm to the road did cause some damage to them. We saw the hire bikes when we checked into the final parador at Caceres and while these may have been ok on the farm track our road bikes were not and we had to push then for the 2.4KM. The farm is a fabulous spot we would not have wanted to miss but it should be clear that it is not suitable for road bikes and that there are unfenced off cattle. Also while we did receive the revised route for the last day the instructions were pretty useless and we just used the maps. We did miss though the road book and got a bit lost in the smaller villages.

CO2 footprint offsetting

This holiday produces a carbon footprint of 0,6326 tonnes of CO2. (The calculation includes taxis, luggage transfers and accommodation for every traveller).

We will compensate the CO2 footprint for each booking through tropical reforestation projects in collaboration with the CeroCO2 platform.

Committed to sustainable tourism