Self Guided Walking Holidays & Cycling Holidays

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Francisco Pizarro statue, Trujillo


  • Cycle the historic lands of Conquistador Explorers
  • End each day in luxury at a Parador Hotel
  • UNESCO city of Caceres
  • Ride across the ancient Roman ‘Ruta de la Plata’
  • Plaza Mayor of Trujillo and its Arab Fortress

Cycle the rise and fall of Spain’s historic ‘Golden Era’. Spend each night in luxury Parador Hotels, lovingly restored medieval palaces, castles and convents.

Extremadura, Land of Conquistador explorers, boasts a wealth of perfectly preserved medieval towns, taking you back in time to the region's 16th century heyday. From the palace of Parador Oropesa, you’ll ride across rich agricultural lands and via sections of the ancient ’Ruta de la Plata’ to the 12th century walled market town and Moorish ruins of Plasencia.

Cycling through the birdlife of Monfrague National Park, leads to the architectural splendours of Trujillo and UNESCO city of Caceres, home to explorer Francisco Pizarro. The exquisite Parador Caceres, a Renaissance palace in the heart of the old quarter is a stately end to this explorers adventure.

Day 1

Arrive Oropresa

South West of Madrid (1 hr 40min by train), Oropresa is
the gateway town to your historical cycling tour. Parador Oropresa was the former ancestral home of the Alvarez de Toldeo family dating
back to the 15th century, when Francisco Alvarez de Toledo was
Viceroy of Peru. Over the centuries the Museo de Oropresa has been a refuge for
monks, soliders, nobility but now provides luxury and comfort for cyclists!

Overnight: Oropesa

Day 2

Oropesa to Jarandilla de la Vera

After your bike fitting, it’s gentle beginnings across the flat lands of Extremadura. Cycling northwest towards the Gredos Mountains, Mediterranean forests line your route on the approach to Jarandilla de la Vera. Once home to Emperor Charles V, Parador Jarandilla is a 15th century castle nestled amongst orange trees, olive and almond groves.

Cycle: 55 km or 67 km

Overnight: Parador Jarandilla de la Vera

Day 3

Jarandilla de la Vera to Plasencia

Today’s ride follows the ancient Roman ‘Ruta de la Plata’ (silver route) to the market town of Plasencia. Retaining much of its 12th century city wall along with 68 towers, the double cathedral complex and Moorish ruins are a testimony to the rich Islamic and Christian history. Your Parador tonight is the delightfully converted 15th century Santo Domingo Monastery.

Cycle: 59 km or 69 km

Overnight: Parador Plasencia

Day 4

Plasencia to Monfrague

A region famed for raising the fierce ‘El Toro’ and black ‘Iberico’ pig, Monfrague National Park is also a bird lover’s paradise. The rocky outcrops are populated by Egyptian, Eurasion Black and Griffon Vultures. Spending the evening in lovingly restored Casa Rural, your hosts will be happy to provide further guidance about the rich flora and fauna in this region.

Cycle: 42 km

Overnight: Monfrague

Day 5

Monfrague to Trujillo

A peaceful pine scented route takes you from the rich bio-diversity of Monfrague to the conquistador’s town of Trujillio. Once the Santa Clara convent, the restored renaissance arches preserve the peaceful ambiance of Parador Trujillo. With two nights here there is plenty of opportunity to soak up your serene surroundings from the comfort of the poolside.

Cycle: 49 km

Overnight: Parador Trujillo

Day 6

Walled town of Trujillo

As one of Spain’s most significant cultural and historic towns there is a choice of two scenic loop rides. Home to conquistadors; Fransico Pizarro, Diego Parades and Hernan Cortes, Trujillo’s labyrinth of medieval streets, churches and historic houses sprawl up the hillside. If you prefer to explore Trujillo on foot today, we’d suggest starting at the Arab fortress in Plaza Mayor.

Cycle: 60 km or 32 km

Overnight: Parador Trujillo

Day 7

Trujillo to Caceres

Cycling through sleepy villages, country lands soon give way to the UNESCO town of Caceres. A crowded skyline of turrets, storks’ nest and church spires, Caceres is feast of sightseeing which will take you back to the golden age of Spanish Explorers, Moorish rule and across the ancient route ‘Via Delapidata’, used by pilgrims heading for Santiago de Compostela. Your final Parador this evening is an exquisitely preserved 15th century Renaissance palace.

 Cycle: 55 km

Overnight: Parador Caceres

Day 8

Onward Travel

Depending on your onward travels plans, you may wish to further explore Caceres, or take a direct train service to Madrid (3 hrs).

Single Rooms & Solo Cyclists

If you require single rooms within your party we would be happy to accommodate you although there is a single room supplement payable. Unfortunately this tour is not available to solo cyclists.


Breakfast is included each morning. Breakfast is a leisurely affair and adequate time should be allocated. Lunch and dinner are not included. Most accommodations are happy to provide a packed lunch - this should be requested on arrival. Dinner is available either at your accommodation or nearby bars, cafes and restaurants.




Parador - Oropesa

Parador - Oropesa

Once the ancestral home of the Alvarez De Toledo family, the Oropesa was the first converted Parador in this historically, luxurious, unique hotel collection.







Parador – Jarandilla de la Vera

Parador – Jarandilla de la Vera

Jarandilla de la Vera has hosted guests, including Emperor Charles V since the 15th century. From the poolside, peaceful gardens extend to the Tietar River.







Parador – Plasencia

Parador – Plasencia

Located on an ancient pilgrimage route this 15th century monastery greets you with thick stone walls, vaulted ceilings and Gothic interiror.







Casa Rural – Placio Viejo

Casa Rural – Placio Viejo

Nestled in 600ha of farmland, The Placio Viejo is a lovingly restored traditional country house, dating back 200 years.







Parador - Trujillo

Parador - Trujillo

Occupying the former convent of Santa Clara this Parador boasts two beautiful cloisters, which retain the peaceful ambiance and tranquillity of this historic building .







Parador - Caceres

Parador - Caceres

Entering via the Arco de la Estrella, the UNESCO listed Parador Caceres is located in the heart of the old quarter is one of the collections most elegant and exquisite properties.




When to go?

This tour is offered from March to June & from September to November.

July and August are the hottest months of the year, with little to no rainfall. The temperatures rise into the mid 30 degree Celsius during the day. We do not offer this tour in July and August as it is too hot for cycling.

June and September, just before and after summer, are dry and sunny with some hotter days. March, April, May, October and November are cooler, still with plenty of sunshine. Always make sure to stay hydrated and carry plenty of water. It is also advised to wear skin protecting clothing and use sun cream/screen.

Grade & Terrain

Itineraries on this cycling trip are graded Moderate. Occasionally you may encounter a few moderate slopes. However, the ascent is not too difficult or prolonged. You will cycle principally on quiet country lanes and some busier roads when approaching towns. Please always mindful of other road users.

Daily distance usually cover around 45km—55km and include some sections of hillier terrain. This is a perfect trip for active travellers that enjoy an evening of comfort and history after a day in the saddle.

Navigation, Route Notes & Maps

The route notes that accompany each itinerary give a step by step, turn by turn account of your route to give you continual points of reference.A pre-loaded GPS is also available should you require, please contact us for details.

Baggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.

Rental Bikes

Giant Argento 24 speed touring bikes are available for hire. Rental bikes come equipped with a basic repair kit, pump and helmet (though we recommend using your own). Male and female frames are available. E-bikes are also available on this trip which offers a boost on the hills are the legs need a little help pedalling.

If you’d like to hire a bike, please let us know your height and frame size you currently ride.


If you would prefer to bring your own bicycle please
ensure it is thoroughly serviced and is an appropriate bike for this trip such
as a Giant Argento, Scott Sub, Trek 7200 or similar. 

Travel Insurance

It is a requirement of booking this tour with Macs Bike that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.

General Information

The distances and ascents/descents are approximations of the recommended routes. Please be prepared by packing all necessary items, for example, proper rain gear, sun hat, sunscreen. Your information pack has detailed advice and a kit list on what to take. This includes good waterproof gear, sports shoes, and lots of other useful bits and bobs.

Getting to Oropesa and from Caceres

Getting to Oropesa

Madrid Airport bus runs directly to Madrid Atocha train station. From here, there is a direct train service to Oropesa (1hr 40mins).

A taxi from Madrid Airport to Madrid Atocha train station will cost approximately €30 and take around 30 mins depending on the time of day.

Private transfers from Madrid or Madrid Airport to Oropesa can easily be arrange, please contact us for prices.

From Caceres

Train: There are regular trains from Caceres to Madrid Atocha train station (3hr 30mins).

Private transfers from Caceres to Madrid or Madrid Airport are available, please contact us for prices.

Trains in Spain can be booked in advanced through the RENFE website. 


  • 6 nights in 4* Parador Hotels, 1 night Country House
  • 7 Breakfasts
  • Detailed route notes with maps
  • Baggage transfer throughout
  • 24/7 local partner and UK telephone support


  • Lunches, dinners, snacks and drinks
  • Entrance fees (where applicable)
  • Travel Insurance
  • Transport should you need to skip a stage
  • Bike Hire


  • Additional nights
  • Bike Hire
  • Half Board

We are often asked the following questions and I hope that you will find the answers useful. Please don’t hesitate to contact us for more advice from our team.

How far in advance do I need to book?

We suggest you book as soon as your plans are finalised as the Paradors can get very busy during late spring and early autumn months. You will find up to date availability on our website and please give us a shout if you have a query.  

How fit do I need to be?

The roads in this region of Spain are generally not difficult to cycle. You may encounter some more challenging sections of road, but these usually don't last for long. It's a good idea to get out on your bike for a couple of consecutive days in the lead up to your holiday so you get used to riding back to back days. Cycling distances on this holiday are broken up with opportunities to stop for coffee in village plazas and plenty of panoramic photo opportunities.

How do the baggage transfers work?

Your bags will be transferred between your accommodation. Just leave them at the reception at your hotel in the morning and they will be picked up and taken to the next overnight stop. Please limit your luggage to one bag per person of no more than 20kgs.

What personal equipment do I need?

You will need comfortable shoes and clothes to cycle in (layers are always a good option), a daypack/hydration pack and sunblock. A full equipment list will be provided in your info pack.

When is the best time of year?

March to June and September to October are just about perfect conditions.  Daytime temperature can vary from late teens in March to the late twenties in June. The spring months also offer the best of Extremadura’s flora and fauna. September through to November deliver warm days of cycling and fewer tourists make for prime time visiting.

What happens if I can’t cycle a stage?

You can use public transport or local taxis to continue to your next overnight stop. In some cases the baggage transfer service that takes your bags on to your next accommodation may be able to assist, but this is not guaranteed. Our local office can assist with helpful advice should you need to arrange transport for yourself or anyone in your party.

Memorable destinations are the reward for very hard biking


The highlight of this trip are the destinations - the Paradors where you stay, the castles to explore in Oropesa and Trujillo, the beautiful old cities of Plasencia, Trujillo, Caceres. Exploring the castles will be one of my best memories from this trip. However, the biking... you see very few local bikers for good reason. This trip is for people who ENJOY BIKING HILLS all day long. You have been warned! We are in our 50s and bike 3 times a week 18-30 miles each time. We were not prepared for these hills and ended up walking many of the inclines or finding alternate routes to avoid inclines so steep they even warn the cars. Also, you are biking primarily on roads with cars whizzing by the entire time. Drivers were all very careful to avoid us, however the constant traffic does not make it a relaxing ride. So only book this if you can handle hilly terrain or plan to rent an eBike.

World traveling couple

Massachusetts, USA


Exception Trip in Spain


We stayed an extra night at Oropesa and Cacares and would recommend that. Oropesa Castle, next to the Parado is very authentic I am glad we had downloaded the route to a Garmin as that made navigation it easier. Using helped us find the Parador in Cacares. The Google Translate app and Spanish dictionary on the phone was very helpful. Craig Dickson from Macs is excellent. Much appreciated getting the route notes early before the trip.

Paul M



On balance I'd recommend this trip


Very good historic accommodation. Food and drink were of a very high standard without being fussy. Local agent very helpful without being intrusive. If you travel there by train from Madrid Atocha, make sure you arrive at station in plenty of time. It is not obvious where the train leaves from and we were given wrong info at enquiries. The holiday involves a lot of cycling across open plains with little variety of scenery on straight main roads. But there was little traffic and what there was, was respectful of cyclists. We did this in mid March and it was pleasantly warm after chilly starts. It might be too hot for cycling mid summer as much of route lacks shade. Recommend the circular cycle on day 6 around Trujilo. It takes you through some contrasting countryside, including green wooded hills. Special mention of Placio Viejo...Senora cares very much about the food she serves and she herself is a warm and charming lady.

One of Mac's Customers



Our first but not our last


This was our very first cycling holiday. I chose an ebike so I could keep up with my husband who has been cycling for years. It was a great choice. I turned it off on the flats and downhill, and I flew up the many hills without breaking a sweat! Just choose the assist level according to how much of a work out you want - but with the assurance that you won't be left behind and walking up the hills if you are not as fit as your super fit husband! The cycle route was lovely. Quite hot - even in September - and the countryside was arid but beautiful. We cycled 50 to 70km a day and chose to not stop for too long along the way but rather to get to the final destination for each day. The stopover towns were truly amazing and worth an afternoon and evening to explore and soak up the atmosphere. There were very few tourists, the towns were very authentically Spanish and we loved the fact that not many people could speak English. The ancient town centers were beautiful and our Parador accommodation was excellent. What a privilege to stay in 14th century castles or 15th century convents ....... It was like staying overnight in a museum! Macs Adventures chose cycle routes for each daughter were scenic and rural and quiet. Some roads were virtually traffic-free. We didn't struggle cycling on the other side of the road (in South Africa we drive on the left) and the other road users were considerate and always took a wide berth around us. We also loved the farm stay. Out in the middle of nowhere. Sheep bells ringing in the fields and wild deer snorting nearby all through the night (rutting season apparently). And so many vultures soaring overhead in the heat of the day. Would we do it again? In a heart beat. It is so satisfying to see the world not from the confines of a stuffy hot car, but with the breeze against your skin, smelling the glorious aroma of the crisp morning air, the sheep and cattle farms, the oak tree forests etc AND getting some good exercise too!!


Cape Town


Awesome trip!


We cycled the Land of the Conquistadors with a 30month old toddler and it was awesome! The cycling is really not difficult. There are some hills and some steep climbs, but generally not to long sections of climbs usually the climbs were followed by the most epic descents! Also all the cycling is tarmac, so really the climbs on tarmac vs. gravel is much easier. Very well organized! The route notes were detailed and easy to follow, as a back up we also used google maps and could also easily program in the via points on the maps. When the route maps state a section of road will be busy, then it usually was, but mostly there were secondary roads which were quiet. We also found the drivers in Spain very conscientious and careful around cyclists. We did the tour end of June, beginning of July and it was very hot, I would recommend maybe end May. Mac Adventures did warn us end of June might be very warm, but due to work it was the only time we could go. My husband took his own bicycle and I rented one. The rental bicycle was also awesome! Lovely bicycle, just the right size and has everything you could need. The Parador Hotels are amazing and was truly an experience! Lovely old castles and monasteries, excellent services and wonderful breakfast, really lovely luxury accommodation, which is awesome after a day cycling. In general in Spain, we found the Spanish quite a bit of a challenge, even if you know some phrases the pronunciation might still be an issue. We found google translate really came in handy. My favorite towns on this tour was Oropesa and Trujillo. There were also some lovely swimming spots on day 1 and 2. Wonderful scenery! We cycled past so many cherry farms! Spanish cherries are the best! Would really recommend this! What an experience! Memories were made we will cherish forever.


South Africa


Memorable Medieval Spain


The website description is an accurate representation of the holiday. Generally the destinations are more interesting than the routes there, with notable exceptions, eg the cycle through Monfrague Park. I found the last 2 days' cycles particularly uninspiring. Day 3 was saved by the optional detour, but adding this makes for a challenging ride. Colourfully abundant roadside wild flowers were particularly impressive on day 2.

Ward wards

High Wycombe


Stunning wild flowers


Late May was a brilliant time for this trip - the fields were full of wild flowers and the temperature not too hot (but sun could burn). The Paradors were impressive. As occasional cyclists in our late 50s we found the cycling more challenging than ideal but worth it for all the other benefits. Would recommend the e-bikes although you still need to pedal hard, even if you get up the hill faster!




Land of the Conquistadors: Cycling the Paradors

4.3 7


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