Madrid to Lisbon

Journey off the beaten path from Madrid to Lisbon, traversing the picturesque landscapes of Extremadura and Alentejo. Immerse yourself in Spain and Portugal’s rich cultural heritage, savouring traditional cuisine and discovering charming towns along the way.
The freshest Food and history galore in medieval cities, Iberia's wonders.

Top Highlights

What’s Included

We design unforgettable and luxurious journeys just for you. Our bespoke trips include:

Best Time to Visit

This wonderful itinerary lends itself to year-round exploration.  During all seasons, the medieval towns of Spain delight with plenty of opportunities for exploration, culinary excellence, and cultural activities.  As is often the case for Southern Europe, enjoy the spring or fall months for the most pleasant climate for touring.


Arrive in Madrid


Begin your journey in Madrid! The Spanish capital is a cultural and social behemoth that attracts repeat visitors from around the world. It has something to tempt every visitor and our travel designers can deliver extraordinary experiences that uncover what all the fuss is about! After arriving at the perfectly appointed, luxurious Hotel The Principal in the city centre, you meet your guide and stroll through the oldest districts of the city. Start from the Arab wall of the tenth century and pass through monuments bequeathed by Austrian and Bourbon dynasties as you explore. After going on a tapas bar crawl with a local expert, overnight in your hotel and prepare for the next day of exploration through the Prado Museum and the Royal Palace, the largest of its kind in all of Europe.

With a large array of shorter experiences such as Flamenco shows, and longer day trips to medieval gems such as Toledo, our passionate local guides will tailor your days to your interests and goals. One thing is for certain: you will want to return to Madrid!

Suggested Accommodation: Hotel The Principal

Caceres, Spain

After taking in the culture of Madrid, you will transfer to Caceres, one of Spain’s prettiest medieval villages. (A true accomplishment in a country with so many!) Caceres is the result of centuries of Roman, Northern Gothic and Italian Renaissance styles, and an outstanding example of a city that was ruled from the 14th–16th centuries by powerful rival factions. This is reflected in its omnipresent medieval fortified houses, palaces and towers.

Feel like a time traveller as your guide brings alive these incredible historical influences, as well as the confluences of Moorish and Christian forces for you today. We suggest an overnight in Caceres’s remarkable Parador, made up of two medieval aristocratic homes full of modern comforts.

Suggested Accommodation: Parador de Caceres

Évora, Portugal

On your way to Évora, we have a real treat in store for you. Enter Dehesa, the landscape that is the ideal ecosystem for the world-famous “pata-negra” Iberian pigs, the source of the best quality ham in the world. Marvel as you watch the professionals of curation and carving, an art passed down from generation to generation.

Once you arrive in the UNESCO World Heritage city of Évora, arrive at former convent (founded in 1485) turned luxury hotel, situated right in front of a Roman temple honouring the Goddess Diana! Choose to explore the serene and beautiful countryside, dine in farm-to-table establishments, or simply promenade Évora’s perfectly preserved wonders.

Make sure you don’t depart before you’ve had a chance to see the 16th-century “Chapel of Bones” in Évora, a hauntingly unique place of contemplation. Its walls and pillars are adorned with the bones and skulls of thousands, serving as a macabre yet thought-provoking reminder of life’s transience.

Suggested Accommodation: Pousada de Évora


Welcome to Europe’s second-oldest capital, the effortlessly elegant Lisbon! This city is both modern and full of old-world charm, propelled along by a friendly and worldly population. The city is built on seven hills, each one offering gorgeous views, excellent restaurants, lively bar scenes and winding streets with homes in warm shades of red, orange, and yellow. Over the centuries, Lisbon has been ruled by Romans, Moors, and Germanic tribes, each leaving their distinctive mark on various neighborhoods. From the Moorish influence in Alfama, to the colonial-era structures of Belem, Lisbon offers hidden histories everywhere you turn.

Exploring Lisbon is a real delight with so much history and beauty to see, we highly recommend a full day tour to savour all of its historical and culinary highlights. The Portuguese are master bakers; the custard tart is ubiquitous, along with plenty other decadent treats not to be ignored. On the savoury side, Lisbon takes full advantage of its sea-side position, and you will find fresh and delectable seafood throughout its restaurants. Outside the city, we recommend spending a day discovering the outstanding castles in Estoril, Cascais, and Sintra.

Suggested Accommodation: Hotel BritanIa

Depart from Lisbon

We design each itinerary around you, so this suggested itinerary is a starting point that we can tweak or transform into something just for you.

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Our unique approach to planning transformative experiences ensures our clients gain more than just a vacation: they come away with a greater understanding of the world, their place in it, and how the journey has enriched their lives.