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
  • Ride across the ancient Roman ‘Ruta de la Plata’
  • Visit Trujillo Castle, home of the Casterly Rock in Game of Thrones
  • The UNESCO city of Caceres
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. Cycle through the wonderful sounds of birdlife in Monfrague National Park, leading to the architectural splendours of Trujillo. Home to explorer Francisco Pizarro and Trujillo Castle, the location used for Game of Thrones Casterly Rock, you will get to spend two nights here to explore this town. The final section of the trip ends in the UNESCO town of Caceres, staying in a Renaissance palace in the heart of the old quarter. This is a lovely way to complete this explorer's adventure.
Read All
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 Type:

Slower Adventures | Where walking and cycling meet easy-going exploring, our Slower Adventures are the perfect combination. Most days are filled with picturesque journeys with some free time to dive into the destination and experience the people, local food and culture as you go.


Leisure Cycling | Leisure Cycling

This trip is suitable for:

Solo Travellers

As a guide, we would suggest that the minimum age of traveler this tour would be suitable for is: 16 Years

Ideal if you have an interest in:

  • Off the Beaten Track

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?
How fit do I need to be?
How do the baggage transfers work?
What personal equipment do I need?
When is the best time of year?
What happens if I can’t cycle a stage?


Day 1 Arrive Oropesa Day 2 Oropesa to Jarandilla de la Vera 42 miles / 42 km Day 3 Jarandilla de la Vera to Plasencia 42 miles / 67.5 km Day 4 Plasencia to Monfrague 27 miles / 44.5 km Day 5 Monfrague to Trujillo 30 miles / 48 km Day 6 Circular ride from Trujillo; optional rest day 39 miles / 62.5 km Day 7 Trujillo to Caceres 34 miles / 55 km Day 8 Onward Travel

Blog Articles

You May Also Like

  • 8 Days 7 Nights
    Cycle Andalucia: Seville to Cadiz
    Journey across Andalucía by bike, pedal from Seville to Cadiz staying in unique accommodations.
    • Cycle through Andalucía's white-washed villages
    • Explore Seville's old alleyways and sunny plazas
    • Relax with a beachside cerveza in Cadiz
    From $2,689.00
  • 8 Days 7 Nights
    Cycling in Catalonia - 8 Days & 7 Nights
    Enjoy traffic-free rural trails through olive groves, vineyards and orchards as you pedal Catalonia.
    • Cycle the dramatic coastline of Catalonia
    • Sample outstanding Catalan cuisine and local wines
    • Includes hire of a good quality mountain bike
    From $1,380.00
  • 8 Days 7 Nights
    Cycling Camino Frances: Leon to Santiago
    Complete the final stage of the ultimate European pilgrimage from León to Santiago de Compostela.
    • A classic ride for adventurers and pilgrims alike
    • Pedal the lush Galician landscape
    • Authentic villages and gastronomic excellence
    From $1,285.00

The Macs Way

  • Tried & Tested Adventures Tried & Tested Adventures
  • Freedom Freedom
  • Book with Confidence Book with Confidence
  • Expertise Expertise
  • Positive Impact Positive Impact
Built with our expert knowledge, to suit you.
  • Knowledgeable and helpful specialist trip planners
  • Wide variety of tours to suit all interests and experience levels
  • Start on any date that suits you
  • Choose your ideal trip length and difficulty
  • Range of accommodation comfort levels
  • Choice of trip styles
Authentic adventure travel experiences on your own terms
  • Choose your own travel companions
  • Walk, cycle and explore at your own pace
  • Make your own decisions
  • Choose your own path
  • Indulge your passions
Feel secure in making the right choice for your precious adventure time
  • 18,000+ unbiased trip & service reviews
  • Feefo Platinum Award 2023
  • 25,000+ travelers trust us each year
  • As featured in the Guardian, Times, Nat Geo Traveler
  • Founder owned & operated since 2003
  • 100+ passionate team members across the US, UK & Europe
You can be confident that every detail of your journey has been expertly planned
  • Carefully planned adventures
  • Quality, hand-picked accommodations
  • Seamless and reliable arrangements
  • Comprehensive trip information & insider tips
  • Detailed maps, route notes and mobile GPS app
  • Helpful 24/7 support should you need it
Travel the right way and make a positive impact
  • Travel responsibly
  • Explore off the beaten track
  • Support locally owned businesses
  • Engage with local communities
  • Minimize your impact
  • Maximize the benefit of your travel
  • Challenge yourself & grow
$ - USD - US Dollar
Country/Region name: