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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

A fabulous cycle tour through the Land of Conquistadors with a touch of luxury!

  • A very special cycle route through this magnificent area of central Spain combining rustic beauty with a touch of luxury.
  • Unique ****star Parador hotels in beautifully restored historic palaces, castles and convents with enticing swimming pools!
  • Discover the magnificent medieval architecture of  the spanish conquistadores of the Americas in Oropesa, Plasencia, Trujillo...
  • Visit the World Heritage city of Caceres with its impressive medieval monuments and main square.
  • Cycle through the terraces full of olive groves and cherry blossom in the foothills of the dramatic mountains of Gredos.
  • Experience the wild beauty of the Monfrague National Park with eagles and vultures swooping overhead.
  • Explore real Spain as this cycle route passes through the beautiful regions of Toledo and Extremadura.


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.

Cycling surface:

Tarmac: 98.6% Cycle track: 1.4%

Day 1: Arrival to Oropesa

Your arrival to Oropesa, which can be easily reached by train from Madrid (1:40 h). Arrive with time to explore this beautiful medieval town, lose yourself in the cobbled streets and discover its historic gems!

Day 2: Oropesa to Jarandilla de la Vera

Your cycling adventure begins today! Through typical Mediterranean woodland, your route leads you along 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. Señora de la Torre. Your stay tonight is in a spectacular castle that once hosted Emperor Charles V for several months!
34 or 41 miles (55 or 67 km) / Climb: 612 m

Day 3: Jarandilla de la Vera to Plasencia

Today's cycling route takes you through peaceful countryside to the medieval market town of Plasencia. Since the days of the Conquistadors, this walled town has enjoyed a strategic location on the historic 'Ruta de la Plata'. Palaces, ancestral homes and significant religious buildings make up the architecture of this beautiful city nestled on the bank of the Jerte river.
36 or 42 miles (59 or 69 km) / Climb: 525 m

Day 4: Plasencia to Monfragüe National Park

Cycling south towards the Tajo river, you will reach the stunning National Park of Monfrague, a well-known place for all bird watching enthusiasts, where you can see the rare black vultures, black storks... The landscape here is a unique juxtaposition of farming land and cork and oak trees. The farms in this area are dedicated to raising Spain's famous wild bulls and the black "iberico" pig which provides us with the delicious 'jamon iberico'.
21 miles (33km) / Climb: 383 m

Day 5: Monfragüe to Trujillo

Today you cycle through beautiful Mediterranean woodland to the town of Trujillo, one of the area’s most important historic and cultural towns and certainly one of Spain's finest gems! The walled hilltop town, which overlooks the expansive countryside, dates back to 600 BC. Several of Spain's most famous conquistadors such as Hernan Cortes who conquered the Aztec empire and Francisco Pizarro who conquered the Inca Empire, 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) / Climb: 427 m

Day 6: Trujillo to Caceres

The scenery of this last day 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) / Climb: 350 m 

Day 7: Departure or extra nights

Why not to take one or two extra nights to relax and enjoy this fabulous destination? 



Day 1 

Your hotel is a beautifully restored 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 an amazing location!

Day 2 

Your hotel is a tastefully renovated palace-castle from the 14th century. It lies sheltered in the middle of the Vera and Tietar 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, ‘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 

This Parador is an impressive historic building just inside the walls of the city. The hotel is in the former convent of Sto. Domingo, founded by the Zuñiga family in the mid-15th century.


Day 4 

A charming country house dating back to the 19th century, set in acres of traditional farmland. Due to its privileged location, at the foot of Las Corchuelas Mountain Range in Monfragüe´s National Park. It is a unique and incomparable destination to enjoy the peace and tranquility of this special place. 

Day 5 

In the historic city of Trujillo, birthplace of explorers, this lovely hotel is set in the 16th century convent of Santa Clara. Outstanding features of the interior include two beautiful cloisters with Renaissance arches and columns drenched in sunlight. Ideal for relaxation and leisure, the hotel has spacious, quiet and pleasant lounges and noble bedrooms with antique wooden furniture. One of the most impressive spaces is the breakfast room, a beautifully decorated restored chapel.

Day 6 

The Parador de Cáceres represents the harmonious union of two palaces belonging to marquises 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.The hotel is conveniently situated in the old historic centre.


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: 163€
  • Solo Traveller supplement: 296€
  • Half board / dinners (wine not incl.): 160€
  • Bike hire: 100€
  • Electric Bike hire: 150€
  • GPS rental (one per group): 30€
What´s included?
  • 5 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: 163€

Half Board

Half Board (per person): 160€

Bicycle rental

Bicycle Rental (per bike): 100€

Electric Bike Hire

Electric bike rental (per bike): 150€

GPS rental

GPS rental (one per group): 30€

Extra night

Extra night in Madrid: Price on asking.

Extra night

Extra night in Caceres (price on asking)


Transfer Madrid-Oropesa (up to 6 persons per taxi): 170€


Transfer Caceres-Madrid (up to 6 persons per taxi): 350€

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.



The organisation of the tour...
...was fantastic, flawless and gave us total ease of mind. The pre holiday instructions were really clear so getting to the starting point was no hassle at all. All our hotels were all aware of our trip and took care of bicycle parking and helped with luggage transfers. Each day our luggage was successfully transferred to the next location without any hassle or glitches. On one of the days it rained persistently that we felt uncomfortable to cycle that day and Away from the Crowds so kindly arranged for us to be transferred by taxi to the next destination. The cycle tour daily itinerary instructions were impeccable, they were so detailed and very simple to understand. We didn't have any troubles navigating from Parador to Parador. The hybrid bicycles we hired were great, although we had a chain break they were able to organise a mechanic to fix the bike to get us moving again. The holiday, the route and the idea is exceptional! Cycling from town to town, visiting various Paradors and the beautiful old towns they're in was truly an unforgettable experience. We had such a great time... we highly recommend this tour and Away from the Crowds as a great tour operator! ChiChi Wang

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. 

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. Ged Bell.

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.

We 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! Diane ans Tim Morris.

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

Our overall impression...
...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. Antonia Lanigan.

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. Charlotte Taylor. 

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.

Besides, you can offset your flight emissions here:

Committed to sustainable tourism