This tour covers the land of the Spanish Conquistadors that grew in wealth from the conquest of South America and as a result boasts a string of outstanding settlements rich in history and architecture. Starting from the old castle of Oropesa in West Spain, the tour leads along the south side of the Gredos Mountains in the La Vera region, and visits three beautiful old cities :- Plasencia, Trujillo and Caceres, packed with history and a wealth of charm.

Pedalling on your 'trusty steeds' through a landscape rich in agriculture with excellent wines and long culinary traditions, you can savour the rural life and enjoy the spectacular bird life and beauty of the Monfrague National Park. By including wonderful paradors for your overnight stays, we know you will feel fully embraced in the rich history and charm of this land of the conquistadors.

Holiday details



from £1,550 per person

Based on two people sharing a room

What’s included?

Dinner is included each night.  See what’s included as standard


6 nights

Start & Finish

Starts daily and is circular from Madrid. Tours run from 1 March to 30 June and from 1 September to 30 November 2024



5 historic paradors located in restored palaces, monasteries and castles. There is a swimming pool in 4 of the hotels and all offer excellent service. Dinner is included each night in the hotel

Holiday type


This tour is priced without a guide and you are free to explore on your own.  If you would like a guide for part or all of your trip, we are happy to provide a knowledgeable, local guide

Activity level

Not so gentle cycling. More info...

Electric bikes

Available - £95.00 supplement


5 days of cycling 24 - 40 miles (38 - 64 km) per day


Rolling - most days have a few hills


None - some busy sections of road and one or two with fast moving traffic


  • Extend the tour by staying in Madrid.
  • Add additional nights enroute at any of the hotels

Itinerary day-by-day


  1. 1. Day one


    Arrive at Madrid airport and we will let you have details of the train service to Oropesa which takes about 1.75 hours (Rail tickets are not included). Settle into your 15th Century hotel - a former palace and castle enjoying a columned courtyard. Relax in the pool with its outstanding views over the plains of Campo Arañuelo. Perhaps you will explore the treasures of Oropesa too - its 16th-century Jesuit School and 15th-century church.

  2. 2. Day two

    Oropesa to Jarandilla de la Vera

    Your host will meet you this morning to run through your itinerary and to familiarize you with the route. Then you are off to cycle through typical Mediterranean 'dehesa' with grassland and oak trees towards the foothills of the Gredos Mountains. Once in the foothills you ride on winding roads through terraces of fruit and olive trees. Find your medieval hotel sheltered in the middle of the Vera and Tiétar valley, between gorges filled with water, woods of chestnut trees and oak groves and a stunningly beautiful natural landscape. This castle-palace played host to Emperor Carlos V, so you are in good company!

    42 miles (67 km)

  3. 3. Day three

    Jarandilla de la Vera to Plasencia

    Pedalling through the foothills there are several climbs but none are too long or steep and you are rewarded with great views. The wonderful town of Plasencia is graced with a beautiful cathedral and a historic centre with bustling Plaza Mayor and several palaces. Your overnight stay is in the heart of the city in a former convent dating back to Gothic times.

    36 miles (58 km)

  4. 4. Day four

    Plasencia to Monfrague National Park

    Today you cycle south towards the Tajo River and The National Park of Monfragüe famous for its bird life. Enjoy the sweeping meadows with ancient oaks and cork trees - a land of large farms, dedicated to rearing wild bulls and the famous black “iberico” pig. The largest and best preserved Mediterranean forest worldwide is in Monfragüe, surrounded by hills of oak forests and Mediterranean thicket and dotted with rocks and streams. You will stay the night in a country house hotel within the park.

    25 miles (40 km)

  5. 5. Day five

    Monfrague to Trujillo

    Today we have more riding through the outstanding Mediterranean woodland on quiet roads. Often wild, sparsely populated and always beautiful, the area's rich culinary tradition is based on shepherd's recipes and pork products. The region hides a gem of a town in Trujillo. Birthplace of the conquistadors and stunningly beautiful, this historic town contains an outstanding collection of churches, castles and manor houses that are centred around the Plaza Mayor square. Your overnight stay is in a former convent with double cloisters.

    31 miles (49 km)

  6. 6. Day six

    Trujillo to Caceres

    The last day of cycling is an easy one through a landscape traversed by the Roman's Silver Route used by pilgrims headed for Santiago de Compostela. Your final miles lead into the World Heritage city of Caceres where you find a blend of Roman, Islamic, Northern Gothic and Italian Renaissance styles, fruit of the many battles fought here throughout history. 30 Islamic towers still stand within the Arab walls and narrow cobbled streets lined with medieval, fortified homes and Renaissance palaces form the historic quarter of the city. Your overnight stay in a 14th Century palace provides a fitting end to a remarkable journey through the homelands of the infamous Spanish explorers.

    35 miles (56 km)

  7. 7. Day seven


    Enjoy Caceres and one of the excellent local wines in its small and ancient taverns before departing by direct train to Madrid. This is a 4 hour journey.