Paradors of Extremadura Cycling Holiday
Start / FinishOropesa / Caceres
Distance163 miles/262 kms
This wonderful six night cycling holiday takes you through some of Spain’s wildest scenery and most picturesque medieval towns, past towering mountain ranges and natural parks. Along the route you’ll overnight in ‘Paradors’; unique converted palaces, monasteries and castles – a truly memorable cycling holiday.
Departing from the old castle of Oropesa, you’ll spend 5 days exploring the rich agricultural scenery on the south side of the Gredos Mountains, in the La Vera region of Spain.
If you enjoy medieval architecture, then delightful surprises await in the beautiful old cities you’ll stay in during your cycling adventure. Oropesa immediately sets a high with its winding flag-stoned streets and impressive castle turned Parador. The historic quarter of the ancient walled city of Plasencia is equally stunning, and you’ll love the old Arab fortress town of Trujillo with its many monuments. At the end of the trip the world heritage city of Caceres awaits, with its welcoming taverns and traditional plazas.
Extremaduran cuisine is famous for its Iberian pork and mutton dishes. You’ll find local specialities to be traditionally simple but generous, usually enjoyed with delicious, fresh, local bread.
Of course, the Paradors themselves are notable highlights of this trip. Along the way you will stay in two castles, a Renaissance palace, a 15th century monastery and a convent. Each will offer a totally unique and unforgettable experience.
A reasonable level of fitness is required for this trip as you’ll be averaging around 50km a day. On the whole the terrain is pretty level but you will encounter a few hills along the way.
Itinerary & Map
Day 1: Arrive Oropesa
Oropesa can be easily reached from Madrid by train. On arrival, you’ll have the rest of the day to explore this pretty medieval town, famous for its castle-turned-parador. Enjoy a delicious evening meal in one of the town’s many traditional restaurants before retiring to your room in the parador to prepare for the next day’s cycling.
Day 2: Oropesa – Jarandilla de la Vera, 34 or 42 miles/55 or 67 kms
Set off on your first day’s ride across flat terrain, passing through typical Mediterranean woodlands, towards the foothills of the towering (and often snow-capped) Gredos Mountains. Stop for the night in Jarandilla de la Vera, a small town boasting a number of remarkable medieval buildings and ancient Roman bridges. You’ll spend the night in the wonderful Parador Jarandilla, an ancient castle in the centre of the town.
Day 3: Jarandilla de la Vera – Plasencia, 37 to 43 miles/59 to 69 kms
Leave Jarandilla de la Vera for another relaxing day’s cycling through picturesque Spanish countryside to the walled market city of Plasencia. Plasencia’s strategic location on the bank of the river Jerta has ensured the city’s status, and acted as a magnet for noblemen since the 15th century. Its cathedral and historic quarter is a must-see today. Tonight’s accommodation is a gothic, 15th century Monastery, complete with thick stone walls and vaulted ceilings.
Day 4: Plasencia – Monfragüe National Park, 21 miles/33 kms
From Plasencia cycle south towards the Tajo River and natural park of Monfragüe, which is famous for its bird life. Along the way pass through open countryside dotted with oak and cork trees. The large farms that you pass every now and then use the excellent grazing land to rear wild bulls and iberico pigs.
Day 5: Monfragüe National Park – Trujillo 31 miles/49 kms
Today you continue cycling through woodland to the historical hilltop town of Trujillo. The town was the birthplace of Francisco Pizzaro and his brothers who conquered Peru. It offers a wealth of sightseeing opportunities, including monuments, churches and an old Arab fortress and wonderfully preserved architecture.
Day 6: Trujillo – Caceres, 34 miles/55 kms
Tearing yourself away from the sights of Trujillo, your last day of cycling will give you a final opportunity to explore this beautiful, wild landscape. Making your way through tiny villages, you’ll arrive at the monumental city of Caceres – ready for a gentle stroll through the narrow, cobblestone streets, a cool drink in one of the city’s many taverns and an evening relaxing on a terrace in one of the numerous plazas. Of course, your last night is once again spent in a charming parador, this one an exquisite former palace.
Day 7: End of trip
After breakfast it’s time to check-out and head for home or your next adventure.
Dates & Prices
|2020 Arrival Dates|
|Arrivals daily from 01 March to 30 June and 01 September to 31 October|
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|Deposit per person||£125|
6 x Breakfast
Maps & route information
GPS route data
Bike hire (see supplements)
Transfer Madrid airport to Oropesa (min 2 people) (£90)
Transfer Caceres to Madrid Airport (min 2 people) (£184)
Regular bike with pannier & lock. See practical information (£95)
Electric bike with pannier & lock (£142)
GPS device (1 x per group) (£29)
The bikes provided on this tour are modern alloy framed models with 24 speeds and comfortable saddle with upright riding position.
The bikes come equipped with a rear pannier, lock, odometer and mapholder. Per room also a repair kit, spare inner tube, multi-tool and pump.
We suggest you bring your own helmet for safety and hygiene reasons. Alternatively, helmets can be supplied on arrival but these must be booked in advance.
On this holiday the accommodation is as much a highlight as the cycling. Paradors are national heritage properties which have been restored and sympathetically converted into unique, hotel-style accommodation. These properties were originally Palaces, Monasteries or Castles and a stay in a Parador is always a memorable experience. Also included is a restored farmhouse.
Oropesa: Parador de Oropesa
Jarandilla de la Vera: Parador de Jarandilla
Plasencia: Parador de Plasencia
Monfrague: Hotel Palacio de las Corchuelas * or Hospederia de Monfrague
Trujillo: Parador de Trujillo
Cáceres: Parador de Caceres
* Hotel Palacio de las Corchuelas only accepts payment in CASH.
Fly to Madrid
Take the train to Oropesa
- Date - 04/10/2018
- Name - Alastair Grant
- Service rating - 5.0
- Service comment - Friendly and helpful
- Product rating - 4.0
- Product comment - Excellent except the weather was exceptionally hot hitting 37c. Day One start was delayed due being issued with a half charged battery.
Yes in such weather when there is no shade on some routes we were unable to stop for a picnic break - until we crept under a motorway bridge.
- Flexitreks response - Service rating : Thanks Alastair, we really appreciate it.
Product : Wow, that's hot, so glad you enjoyed it despite the weather!
- Date - 22/08/2017
- Name - Anonymous
- Service rating - 5.0
- Service comment - We had excellent cycle tour prep service from Ally. She was personable and very enthusiastic helping us plan our tour. All questions and concerns were handled in a timely and professional manner. Highly recommended, thanks Ally!
- Product rating - 5.0
- Product comment - The tour bikes provided were priced right and set-up to our specs perfectly.
The accomodations were spot-on as described, fairly priced, and each distinctively memorable... a remarkable experience!
(... as was the epic heat!) ;)
- Flexitreks response - Glad you enjoyed the holiday despite the heat. Also, Ally wants you to know tha she really appreciates the lovely comments about her service.