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Dramatic limestone cliff of Peña Falcón rising above green hills in Extremadura, Spain, illuminated by golden sunset light under cloudy sky.

Cycling in Extremadura - Parador to Parador

7 Days / 6 Nights
Moderate
Dramatic limestone cliff of Peña Falcón rising above green hills in Extremadura, Spain, illuminated by golden sunset light under cloudy sky.

The essentials at a glance

Cycle through Extremadura's historic landscapes from Oropesa to Cáceres, staying in elegant Parador hotels and exploring UNESCO World Heritage sites. The route covers 279 km over 5 cycling days through Mediterranean countryside, the Gredos Mountains foothills, and Monfragüe National Park. Visit remarkable towns including Jarandilla de la Vera, Plasencia, and Trujillo, with their palaces, churches, and conquistador heritage, finishing in the architectural treasure of Cáceres.

Discover a quieter and wonderfully authentic side of Spain on this cycling holiday, where historic towns, wide-open landscapes and centuries of history unfold day by day. The journey leads from Oropesa towards Cáceres through the beautiful region of Extremadura, with the Gredos Mountains forming a dramatic backdrop in the north and peaceful countryside stretching towards the south. Along the way, you cycle through Mediterranean woodland, olive groves and traditional farming landscapes, while magnificent towns such as Plasencia and Trujillo invite you to explore grand squares, medieval streets and palaces built during Spain’s fascinating past.

One of the great pleasures of this journey is the combination of rewarding days in the saddle and exceptional places to stay. Several nights are spent in Spain’s famous Paradores – historic buildings transformed into atmospheric hotels – including castles and former palaces full of character. The route also passes through Monfragüe National Park, one of Spain’s most important areas for birdlife, where vultures and eagles can often be seen circling above the hills. With varied scenery, remarkable architecture and a region still largely untouched by mass tourism, this is a journey that brings you wonderfully close to the landscape, culture and everyday life of inland Spain.

 

Highlights of the journey

  • Stay in atmospheric Paradores, set in historic castles, palaces and former monasteries
  • Cycle through the beautiful landscapes of Extremadura, far from Spain’s busiest tourist areas
  • Experience Monfragüe National Park, renowned for its impressive birdlife and dramatic scenery
  • Explore historic towns such as Plasencia, Trujillo and Cáceres, filled with medieval streets, grand squares and centuries of history

The route

The route follows mostly quiet paved roads through rolling countryside, with regular climbs and descents along the way. The first stages are the most demanding, while the terrain becomes somewhat gentler later in the journey. With almost the entire route on asphalt, the tour is well suited to confident recreational cyclists with a reasonable level of fitness.

Itinerary

See the day-by-day itinerary below.

Arrive in Oropesa, a small historic town that can easily be reached by train from Madrid. If you arrive early, there is plenty of time to explore the old centre, wander through the cobbled streets and take a closer look at the impressive castle that dominates the town.

Your first evening is a gentle introduction to Extremadura and a good opportunity to settle in before the cycling begins the following morning.

Hotel (example): Parador de Oropesa

Your first cycling day takes you through classic Mediterranean countryside and along the foothills of the Gredos Mountains. The granite peaks form an impressive backdrop as you ride through a landscape of woodland, farmland and small settlements on the way towards the fertile La Vera region.

At the end of the stage, you arrive in Jarandilla de la Vera, known for its historic centre and attractive churches. Tonight’s Parador is particularly special: a beautifully restored palace-castle where Emperor Charles V stayed before retiring to the nearby Monastery of Yuste.

Hotel (example): Parador de Jarandilla

Today’s route continues through peaceful countryside and the green landscapes beneath the Gredos Mountains. Along the way, the longer route gives you the opportunity to visit the 16th-century Monastery of Yuste, surrounded by oak woodland and closely connected with the final years of Emperor Charles V.

You then continue towards Plasencia, a historic walled city on the banks of the Jerte River. Its old centre is filled with palaces, churches and noble houses, and the city once occupied an important position on the historic Ruta de la Plata.

Hotel (example): Parador de Plasencia

Leaving Plasencia behind, you cycle south towards the Tajo River and Monfragüe National Park. The scenery gradually changes to the characteristic dehesa landscape of Extremadura, with open grazing land scattered with cork oaks and holm oaks.

Monfragüe is one of Spain’s most important areas for birdlife, and you may spot vultures and eagles soaring above the hills as you approach your accommodation. Tonight is very different from the Paradores: you stay in a peaceful rural property surrounded by nature inside the national park.

Hotel (example): Palacio Viejo las Corchuelas or Hospederia de Monfrague

The journey continues through the wide-open landscapes of Extremadura, following quiet secondary roads through Mediterranean woodland and traditional dehesa. It is a wonderfully peaceful section of the tour, with long views across a countryside where livestock farming remains an important part of daily life.

Your destination is Trujillo, one of the region’s most remarkable historic towns. Its grand Plaza Mayor, palaces and old mansions reflect the wealth brought back by explorers and conquistadors such as Francisco Pizarro, who was born here.

Hotel (example): Parador de Trujillo

Your final cycling stage takes you through a mixture of small villages and broad Extremaduran landscapes. The route remains pleasantly varied as you make your way west towards Cáceres, where the historic centre provides a suitably impressive finish to the journey.

Cáceres is a UNESCO World Heritage city with an extraordinary mix of Roman, Islamic, Gothic and Renaissance architecture. After arriving, take time to explore its maze of narrow cobbled streets, stone palaces and fortified buildings before enjoying your final night in the heart of the old town.

Hotel (example): Parador de Cáceres

After breakfast, your cycling holiday comes to an end. From Cáceres, you can travel back towards Madrid by train, or extend your stay with an extra night and spend more time exploring the historic city.

Another possibility is to continue to Mérida, famous for its exceptionally well-preserved Roman monuments and archaeological sites.

Prices and dates

Prices per person in EUR

The price includes

ACCOMMODATION

  • 6 nights in 4-star hotels and Parador hotels

 

FOOD & DRINKS

  • Breakfast every day

 

CYCLING & EXPERIENCES

  • 5 days of cycling (approx. 279 km in total)
  • Standard bike rental (can be deselected – see details below)
  • Detailed descriptions of the carefully selected routes (route maps, route descriptions, information about relevant tourist attractions and important phone numbers – in English)
  • Access to the route in our GPS app, which also works offline (one access per person)
  • Option for GPX files for use in your own GPS

TRANSPORT

  • Luggage transport between the hotels

 

OTHER

GENERAL

  • Transport to/from Spain
  • Handling fee (€ 25)
  • Travel insurance

 

REQUIRED AND PAID LOCALLY

  • Any tourist taxes at the hotels

OPTIONAL
The following can be selected in the booking form, when you book the tour.

  • Rental of electric bike (selected when booking the tour)
  • Half board (6 dinners)

 

Use the button "Calculate price" on this page to see what the tour will cost with your wanted inclusions.

PARKING
It is possible to park at the first hotel or nearby. Parking cannot be reserved in advance and must be arranged directly with the hotel (expect a cost of approximately €10–20 per day).

Bikes

You can choose from these bikes on the tour.
Dark green touring bicycle with rear rack, front suspension fork, disc brakes, and multiple gears displayed against white background.
Bicycle (Male)

Disse cykler er designet til at kunne modstå tunge belastninger og give høj sikkerhed og komfort selv efter mange timers kørsel i sadlen. Alle cykler leveres med cykeltaske, kortholder på styret, vandflaske, lås, pumpe, reparations-kit og værktøj.

Silver touring bicycle with step-through frame, black rear rack, front suspension fork, and multiple gears displayed against white background.
Bicycle (Female)

Disse cykler er designet til at kunne modstå tunge belastninger og give høj sikkerhed og komfort selv efter mange timers kørsel i sadlen. Alle cykler leveres med cykeltaske, kortholder på styret, vandflaske, lås, pumpe, reparations-kit og værktøj.

Black electric bicycle with step-through frame, rear rack, disc brakes, and battery mounted on the downtube against white background.
E-bike
Option to book an e-bike on the tour
  • These bikes are perfect for long-distance routes
  • All bikes come with a bike bag
  • Map holder on the handlebars, water bottle, and lock
  • Pump, repair kit, and tools

Practical information

Here you can get answers to various questions about the trip
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The price is based upon two people sharing. It is also possible travel alone in a single room. Simply choose "1 person" in the booking form and it will automatically add the single room surcharge.

On this tour you will be on your own supplied with maps, route descriptions and luggage transfers. That means that your time is your own and you have plenty of time to enjoy the stages in your own pace.

 

Check the price quickly
You can quickly check the price of your desired trip without having to fill out any forms. Here’s how:

  1. Click on the "Calculate Price" button (you’ll find it in the "Dates and Prices" section) – this will take you to the first pages of the booking form
  2. Select your preferred date, number of people, room distribution, any extra nights, and any available add-ons you may want
  3. See the price


Get a quote
If you would like a flight included, or changes made to the trip, you can request a customized offer by clicking the "Get Quote" button at the top of the page. Remember to describe in detail what changes you would like.

The booking process
When you book the trip, we will begin booking hotels and arranging all the practical aspects of your tour. This process typically takes 5–8 working days, but in some cases it may take longer for certain bookings. If you arrange your own transportation, we recommend waiting until we have confirmed your booking before making any arrangements.

Dates
If you can select a date in the trip calendar (in the booking form), then this is a possible start date. We regularly update our trips with sold-out dates; these dates will then appear in red/grey and cannot be selected.

On all our cycling holidays it is possible bring your own bike but it also possible to rent a bike for the tour. The bikes you can rent are all perfectly suited for the tour and the local terrain and all bikes are perfectly maintained. If you want to rent a bike on your holiday, then you select this on the booking form.

Equipment included in the bike rental:

  • Saddle bag (water repellent)
  • Handlebar bag (water repellent)
  • Service-set with tools and extra bicycle tube
  • Combination lock

 

Roadside assistance
All bikes are equipped with puncture resistant tyres which means that it is virtually impossible to puncture. No rule without exceptions, so should you experience a punctured tyre then you can quickly fix it by using the tools in the service-set. If the damage is greater than a simply puncture then you simply call us and we make sure that your bike is fixed or you will be supplied with a new bike as quickly as possible.

Insurance is included
Insurance against theft and damages are included in the bike rental. Should you have any problems of this nature then all you have to do is to let us know and we will supply a new bike as quickly as possible. Naturally, careless or mischievous behavior is exempt from this.  

Flights to Madrid are not included in the price of the trip. We recommend that you find the flights yourself, for example via www.momondo.dk.
We recommend that you wait until we have confirmed your journey before arranging transport.

Here's how it works:

  •     You book the journey with us
  •     We confirm your journey (usually within 2-5 business days)
  •     You arrange your transport

Get a quote
If you need us to organise your flight for you, you can request a quote for the trip including flights. It often takes about two days to get a quote. Please note that we charge a handling fee of DKK 350 per ticket, which means that you get the flight cheaper by booking it yourself.

On this tour, you stay in carefully selected 4-star hotels and historic Parador hotels, which form an important part of the overall experience. The Paradores are often housed in beautiful historic buildings such as former monasteries, palaces and castles, giving the journey a distinctive atmosphere. Along the way, you stay in charming towns including Jarandilla de la Vera, Plasencia, Trujillo and Cáceres.

Near Monfragüe National Park, you stay in a more rural hotel surrounded by nature, providing a lovely contrast to the historic city hotels. Overall, the accommodation is comfortable and of a high standard, perfectly complementing the tour’s combination of cycling, culture and history.

Breakfast is included every day and is served at the hotels. If you choose the half-board option when booking, dinner is also included. Otherwise, you will find a good selection of restaurants in the towns where you stay overnight, and the Parador hotels are also known for serving regional cuisine.

For lunch, you can use the Bering Travel app to get an overview of places to eat along each day’s route. You can also buy provisions in the towns and local supermarkets before setting off, or ask your hotel whether they can prepare a packed lunch for the day. Drinks are generally not included unless otherwise stated.

Local specialities
Extremadura has a strong culinary identity based on simple, high-quality local ingredients. The region is especially famous for jamón ibérico, produced from Iberian pigs raised in the dehesa landscape, as well as creamy Torta del Casar cheese, Pimentón de la Vera smoked paprika and traditional dishes such as migas extremeñas. Local olive oil, cured meats and wines from Extremadura are also well worth trying along the way.

Luggage transfer is included on this tour. Upon arrival at the first hotel you will be given luggage tags along with the rest of the welcome package. You fill out the luggage tags and put them on your bags where they will remain for the duration of the tour.

Your luggage is picked up from the hotel lobby around 9am every morning and will arrive at your next hotel at 6pm at the latest (often long before that). If there are any special exceptions to the luggage transfer you will be notified upon arrival.

Luggage transfer includes one bag per guest and the bags can weigh 20kg each.

On this tour, you will receive the following documents:

Upon booking
Immediately after booking this trip, you'll recieve a pre-booking-email where you can get a complete overview of your booking. Once the tour is confirmed you get a confirmation email from us along with practical information about the tour.

One month before departure
You will receive a hotel list and final travel documents.

Upon arrival at the first hotel
You'll receive the welcome pack, which contains everything you need for the trip. There will be route descriptions, maps, luggage tags, specific local vouchers and if you have rented a bike, they will also be handed out at the first hotel. The documents are in English.
Notice: On some tours it is necessary to either print the documents yourself or to bring them electronically.

This tour has difficulty grade 3.

Grade 3
Longer distances in hilly terrain, often with steep climbs. The distance is usually 65 – 80 km or 40 – 50 miles per day. Requires good shape and health. We highly recommend that you practice on some longer rides before you leave home.

Read more about our Grading System

Starting in 2025, travelers from visa-exempt countries will need an ESS or ETIAS authorization to enter EU nations. This system enhances border security while simplifying entry procedures. Ensure compliance by applying online before your trip to avoid delays.
You can read more about it here.

After booking this trip, you get access to various discount schemes.

We recommend taking out travel insurance that covers at least illness, accident, repatriation, lost holiday, luggage and liability. As a customer, you are responsible for taking out the necessary travel insurance to cover these costs.

Before taking out insurance, you should check whether you are already covered by travel or cancellation insurance through your home insurance company, credit card or similar - please note that there may be differences in insurance coverage.

Join the special ‘Bering Cycling Holidays’ group on Facebook. Here you'll be notified about new holidays, special offers and much more.

Link to the group

Note: you need to request membership, but everyone is approved.

When you book a trip with us, we plant a tree in Kenya.

Bering Travel partners with Growing Trees Network, which has been planting trees in Kenya since 2020 in collaboration with Seniorer uden Grænser (Seniors Without Borders). The trees are planted with small-scale local farmers in the Mount Kenya region, as well as at schools, where the fruit helps supplement students’ diets and is incorporated into their learning.

The trees are planted using the shamba method – a sustainable approach that combines reforestation with agricultural crops. This keeps the soil covered with vegetation throughout the year, helping to prevent nutrient loss and reduce erosion.

The contribution to tree planting comes directly from Bering Travel’s own earnings and is not added to the price of your trip.

This initiative is not intended as a carbon offset for travel, but as a way to make a positive contribution.

Read more

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