Self Drive from Madrid to Spain’s Medieval Heart

Madrid, Toledo & Caceres

Best time to travel

Apr – Jul, Sep – Nov

Ideal length

7 nights

Perfect for

All

From (incl flights)

€3,099 pp

At a glance

International flights from Dublin to Madrid.
Private airport transfer as well as 4 days’ pre-arranged car rental.
7 nights’ luxury accommodation in Madrid, Toledo and Cáceres.
Explore the very best of Madrid and the Extremadura, from the delicious cuisine to rustic medieval landscapes.
Privately guided tour of Toledo, Caceres and Madrid’s famous San Miguel Market.

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Introduction

Usually associated with sunny weather and seaside bliss, allow us to uncover another side of Spain. With heartlands that are dotted with medieval towns, old stone castles and beautiful olive groves, a fascinating land of culture awaits. On this suggested itinerary, prepare to take a journey back in time to as we whisk you away to Madrid, before venturing deep into the historical Extremadura to explore the historic wonders of Toledo and Caceres.

Trip Overview

Depart from Dublin to Madrid.

Upon arrival in Madrid, your private driver will be waiting to transfer you to city centre. Enjoy a three night’s stay at one of the city’s most luxurious hotels situated along the iconic Gran Via.

Get to know the city like a true Madrileño.

Accompanied by a foodie guide, enjoy a celebration of Madrid’s most delicious tapas during a tour of the famous San Miguel Market. Sample a taste of typical Spanish tapas at select spots in the market from tortilla de patatas to the famed salt cod brandade.

It’s time to head to Toledo.

After collecting the keys to your luxury rental car, set off for Toledo, a heritage town dramatically set atop a gorge overlooking the Río Tajo. Enjoy an overnight stay in a luxurious hotel that was once the former home of historical nobility.

Discover the histories of medieval Toledo.

Explore the protected city, home to marvellous examples of Arabian, Jewish and Christian monuments. Wander the cobbled streets and visit a number of important cultural sites including the ancient Synagogue of Santa María la Blanca and great Cathedral of Toledo.

Continue to Cáceres, one of Spain’s most beautiful cities.

With narrow cobbled streets that twist and climb among ancient stone walls, Cáceres takes you back in time to the 16th-century. Take in the city’s sights during a three night stay at a luxury hotel set within a rustic stone facade.

Take in the ancient sights and sounds of Cáceres.

A treasure trove of medieval fortress-houses and Renaissance palaces take in the most beautiful sights of the UNESCO-protected Ciudad Monumental. Accompanied by your guide, pay a visit to important cultural landmarks such as the Cathedral of Santa Maria and Church of San Francisco Javier.

Transfer to the international airport.

Drop off your rental car and board your flight home. Arrive in Dublin.

Tailoring your holiday

OROKO Itineraries are created with you in mind and no two are the same. These can be used to help plan your trip - or we can design a completely different itinerary to suit you.

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Accommodation

Where to rest your head

Looking for the best accommodation? We've got the contacts

The Principal Madrid Hotel

One of the city’s most luxurious hotel, The Principal Hotel sits along Madrid’s most iconic street of Gran Via, literally translated as the Great Way.

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Eugenia de Montijo, Autograph Collection

Sitting along one of Toledo’s narrow cobblestone streets lies Eugenia de Montijo. A former palace of the Empress Eugenia de Montijo, one can expect ultra-luxurious interiors.

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Atrio Hotel

In between Cáceres’s celebrated Paseo de Cánovas and the Concatedral de Santa María lies the luxury Atrio Hotel. Décor is complemented by numerous works of art.

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What people are saying

OROKO created the honeymoon of our dreams in South Africa. The consultation process was very laid-back and conversational. The whole process overall was really quite quick and smooth. There was no trawling through the internet for hours late at night, weighing up costs and reviews of hotels and transfer companies etc – it was all done for us based on the OROKO travel experts’ experiences – which we found to be absolutely spot on. Choosing a ‘luxury travel’ company was a little daunting: We wanted a special honeymoon without spending silly money – and OROKO worked very well with this brief. Believe me when I say our accommodation could not have been more perfect for us. It really was the holiday of our dreams.

Angharad & husband – Honeymoon 2019