Extremadura and Paradores
Enjoy a touch of luxury as you cycle through central Spain’s sweeping landscapes, staying in beautifully restored historic Parador Hotels. This self-guided, grand cycling tour will allow you to discover a new Parador each night and enjoy the best cuisine that the heartland of Spain offers. Along the way, experience the wild beauty of Monfragüe National Park, a birdlife paradise, with eagles and vultures swooping overhead.
Take in the magnificent architecture in Oropesa, Plasencia and Trujillo, towns built by the explorers who returned from the Americas, before reaching your final destination, the UNESCO World Heritage city of Caceres, with its impressive medieval monuments and main square.
2027 launch offer: £50 per person off all 2027 departure dates!
Itinerary
Enjoy your first Parador and explore the historic town when you arrive in Oropesa, which is easily reached by train from Madrid.
Your tour begins today as you head towards the foothills of the Gredos Mountains, to the beautifully restored castle of Jarandilla de la Vera, where you’ll stay the night. Along the way, cycle through typical Mediterranean woodland, the granite cliffs of the Gredos providing stunning views.
Continue through more peaceful countryside today as you cycle to the medieval market town of Plasencia with its beautiful cathedral and historic town centre. This walled town has long enjoyed a strategic location on the historic ‘Ruta de la Plata’, nestled on the bank of the Jerte River. Take the longer route today for the chance to visit the beautiful 16th-century Monasterio de Yuste, set in stunning oak woodland.
Cycling South towards the Tajo River, you will reach the National Park of Monfragüe, a well-known place for all ornithologists. This farming landscape is dedicated to raising Spain’s famous wild bulls and the black “iberico” pig, which provides us with the delicious ‘jamon iberico’. You’ll find tonight’s accommodation in a fabulous Country Farm hotel.
Today’s destination is one of Spain’s finest gems, the town of Trujillo, reached through typical Mediterranean woodland. Hernan Cortés, Francisco Pizarro, along several more famous conquistadors of Spain called this region home. The perfectly preserved architecture of the town and the impressive bronze statue of Francisco Pizzaro are evidence of the legacy of the conquest.
Your journey continues as you spend this final day cycling through the beautiful small villages and impressive landscapes that line the route to your final destination of Caceres. Explore this UNESCO World Heritage City full of twisting, narrow cobbled streets lined with palaces and mansions whose architecture reflects a blend of Roman, Islamic, Northern Gothic and Italian Renaissance influences.
Departure from Caceres or spend extra nights in the city or the surrounding region.
Arrival: Oropesa
Departure: Caceres
Nearest arrival airport(s): Madrid
Nearest departure airport(s): Madrid
We also recommend travelling by train to all of our cycling holiday starting and departure points. We can help you plan your journey to Oropesa by rail.
Car parking is available on all tours at the first hotel or a nearby public parking location. Full details are available on request. Please do not book travel until an official invoice confirms the cycling holiday.
Route overview
Starting point: Oropesa
End point: Caceres
Total cycling distance: approx. 283 km
Cycling from Oropesa to Cáceres, a route in Spain’s Extremadura region, offers a scenic yet challenging journey through varied terrain. The ride covers approximately 180 kilometers, passing through a landscape of rolling hills, vast plains, and some mountainous areas.
Starting from Oropesa, a historic town known for its medieval castle, the terrain initially consists of undulating hills and agricultural lands, typical of the region. The route soon transitions to the flatter plains of the Tajo River valley, providing easier cycling stretches. However, as the journey progresses towards Cáceres, cyclists will encounter more challenging climbs, especially near the Sierra de las Villuercas, with steeper ascents and rugged terrain.
BIKE HIRE OPTIONS
This cycling holiday benefits from high-quality bike hire options that have been carefully selected for the tour. Each well-maintained bike has modern V-brakes, aluminium wheels and puncture-proof tyres based around a branded frame. Dynamo lights, small panniers, a mobile phone holder, repair accessories, a handlebar bag and a comfortable saddle ensure that you have everything you need for an enjoyable cycle tour.
Standard Unisex Bike
Sizes: XS to XL
Standard Men’s Bike with crossbar
Sizes: XS to XL
Unisex Electric Bike
The electric bikes available on this tour assist up to 25 km/h whilst pedalling. The pedalec motor is in the bottom bracket of the frame and the detachable batteries last for approximately 120 km. Each bike has an illuminated LCD and 8-speed internal hub gears. Only limited numbers are available.
Sizes: S to XL
What’s included
- 6 nights’ accommodation.
- 6 breakfasts.
- Luggage transfers between hotels
- Detailed maps with the trail 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
Not included
- Travel to/from the start and finish (Flights/Trains)
- Evening meals (unless stated)
- Local daily taxes (Payable at the hotel)
- Helmets (Please bring your own cycle helmet with you)
- Water bottles
- Travel insurance
- Bike hire (Rental bike insurance included)
- Bike insurance (unless stated)
- Welcome meetings (unless stated)
- Transfers (unless included)
- SINGLE ROOM SUPPLEMENT: £449 PER PERSON
Check Availability
2026/27 Self-Guided cycling holidays
All prices shown are per person, based on sharing a double or twin room, and exclude flights and bike hire.
Special Offer: £50 per person off all 2027 departure dates!
Contact us for more information, a special price, or call 017687 71700. Offer valid on new bookings only.
NEW FOR 2027
To make a booking, simply use the filter to select the day of the week on which the tour operates. You’ll then see all available tour dates and prices. No payment is taken at this stage.
For all bookings, we require a 20% deposit, with the final balance due 56 days before arrival. An invoice and online payment link will be generated once the tour has been confirmed.
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