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Land of the Conquistadors: Cycling the Paradors

8 Days & 7 Nights 4.3 Read 7 reviews
  • 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.
Graded moderate, you’ll be earning each night of luxury in historic Parador hotels. Cycling days are broken up with picturesque rest-stops, village tapas bar and a wealth of Spanish history. 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.

Tour Style:

Self Guided | Go at your own pace on an independent tour.


Inn to Inn Biking | A classic point to point biking tour, staying in a different location each night

Ideal if you have an interest in:

Foodie Adventures, Wine, Whiskey & More..., Elegance & Unique Stays, Historical Journeys


  • Classic

Activity Level & 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.


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.


If you require single rooms within your party we would be happy to accommodate you although there is a single room supplement payable. 

Solo Cyclists

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.

  • 6 Nights in 4* Parador Hotels and 1 night in a country house
  • 7 Breakfasts
  • Baggage transfer
  • Information pack
  • Detailed route notes with maps
  • 24/7 Emergency telephone support from our office and local partner
  • Travel to Oropesa / from Caceres
  • Bike hire
  • Lunches, dinners, snacks and drinks
  • Personal equipment
  • Travel insurance (required)
  • Additional nights along the route
  • Upgrade you meal plan to half board
  • Bike hire

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.

Getting to the Start

By Bus: Madrid Airport buses run directly to Madrid Atocha train station. From here, there is a direct train service to Oropesa (1hr 40mins).

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

By Private Transfer: from Madrid or Madrid Airport to Oropesa can easily be arranged, please contact us for prices.

Getting from the End

Train: There are regular trains from Caceres to Madrid Atocha train station (3hr 30mins). Trains in Spain can be booked in advanced through the RENFE website. 

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

Luggage 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.

General Information

The distances and ascents/descents are approximations of the recommended routes. Please be prepared by packing all the 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.


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.

How far in advance do I need to book?
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Day 1 Arrive Oropesa Day 2 Oropesa to Jarandilla de la Vera 42 miles / 67 km Day 3 Jarandilla de la Vera to Plasencia 43 miles / 69 km Day 4 Plasencia to Monfrague 26 miles / 52 km Day 5 Monfrague to Trujillo 31 miles / 49 km Day 6 Walled town of Trujillo 38 miles / 60 km Day 7 Trujillo to Caceres 35 miles / 55 km Day 8 Onward Travel

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