Journey across the Iberian Peninsula, through scenic mountains and medieval hilltop villages, between two buzzing European capitals a day trip apart – each with abundant history, exceptional cuisine and easy access to UNESCO World Heritage sites.
Distance & Travel Time
- 625 km (388 miles)
- Travel Time
- 6 hours by car
Road Trip Highlight
- Discover Alentejo, Portugal’s Tuscany
- They say in Alentejo, even time takes its time. A short detour off your scenic route between Madrid and Lisbon will lead you through endless wheat fields and gently rolling plains of Portugal’s largest (yet least populated) region. Dominated by vineyards, olive groves and the world’s largest cork oak forest, Alentejo prides itself on sustainable agriculture and the richness of its land and heritage. It is also fast emerging as one of Europe’s most exciting wine destinations, while still favouring the region’s indigenous grape varieties. Drive along the Wine Route signs, pick up some local bottles from the friendly vintners, and stop in the charming towns of Portalegre, Nisa, Marvão, Castelo de Vide or Alter do Chão in the northeast for a bite to eat. 2 hours from Lisbon / 5 hours and 30 minutes from Madrid
More Experiences Along the Way
The treasures of UNESCO World Heritage Site Évora, one of Portugal’s most beautiful cities, include Neolithic monuments, an ancient Roman temple, a 12th-century cathedral and more. Head Concierge at Four Seasons Ritz Lisbon Luis Miguel recommends Reguengos de Monsaraz, a tiny walled 14th-century town that looks like it’s straight out of a medieval fairytale.
1 hour 30 minutes from Lisbon / 5 hours from Madrid
A Spanish city on the Portuguese border, the hill city Badajoz is home to the Alcazaba Fortress, among other evidence of Moorish influence, and to melt-in-your-mouth Jamón Ibérico. Enjoy a stroll around the historic quarter and some tapas. One of our favourite restaurants for Íberico,ham, among many other meat and seafood dishes, is the quaint and lively Galaxia.
2 hours 20 minutes from Lisbon / 4 hours from Madrid
Home to dozens of Roman ruins, UNESCO World Heritage Site Mérida has been home to Christian, Moorish and Portuguese culture. The combination of these different influences has made it a popular stop for travellers.
Raul Bermejo, Head Concierge at Four Seasons Hotel Madrid, suggests visiting the Roman theatre, the Amphitheatre or the Temple of Diana to experience one of the leading archaeological sites in Spain.
2 hours 50 minutes from Lisbon / 3 hours 20 minutes from Madrid
Toledo is one of Spain’s most historically fascinating cities. A UNESCO World Heritage Site, the city’s historic quarter contains some of the country’s oldest religious buildings, all within walking distance. Set on a hill and surrounded on three sides by the Tagus River, Toledo offers endless views.
After exploring the historic quarter, set your sights on the city from the other side of the river from one of the many viewpoints (such as Mirador del Valle) or restaurants (we recommend Restaurante La Ermita). Every corner of Toledo seems to exude an endless charm, and it’s no surprise why this city is a favourite spot among international travellers and Spanish locals alike.
5 hours 30 minutes from Lisbon / 1 hour 30 minutes from Madrid
Once You’ve Arrived
- Street Art Tour in a Sidecar
Take an exhilarating tour of Lisbon with a professional photographer and a vintage motorcycle. Discover the city’s most spectacular sites, where the photographer offers tips on taking your best shots.
- Day Trip to Sintra
It takes less than an hour from Lisbon to travel back to the age of imperial Portugal and Europe’s original epicentre of Romantic architecture. Don’t miss the storybook Palácio National de Pena, on a hilltop with breathtaking views of the Serra de Sintra and the Atlantic.
- Surf and Seafood on the Guincho Coast
Drive along the Coastal Guincho road – a surfer’s and windsurfer’s paradise, complete with magnificent Atlantic views. Stop at restaurant Monte Mar for Bulhão Pato clams, a local delicacy, then visit Cape Roca, “where the land ends and the sea begins” according to Portuguese poet Luís de Camões. This marks Europe’s most westerly point. Head to the lighthouse for the best views.
More About Lisbon From Our Team
- Local Gems That Can’t Be Missed
Insiders from Four Seasons Hotel Ritz Lisbon share their favourite spots to eat, drink and play around the Hotel.Read More
- Unpacking List
It’s not the things you take with you that define your journey; it’s the experiences you have and the memories you bring home. Explore our Communications Director’s six sensory “souvenirs.”Read More
Four Seasons Hotel Ritz Lisbon
Inside our iconic Hotel, art deco sensibilities mingle with an updated Louis XVI style, and a collection of important modern Portuguese art fills our halls. Outside, views of the city’s rolling hills and brightly tiled exteriors spread out before you.
- Experience Flamenco
The country’s iconic dance is not “just for tourists” – Madrileños have a genuine love for this Andalusian dance form, inscribed on UNESCO’s Intangible Cultural Heritage Lists in 2010. There are plenty of small tablaos we can recommend for enjoying a flamenco performance alongside locals. We can even plan a private lesson.
- Tour the Paseo del Arte
From the Hotel, it’s an easy walk to three of the world’s best art museums: the Prado, with its masterworks by Velázquez; the Thyssen-Bornemisza, with spectacular pieces by the impressionists; and the Museo Nacional Centro de Arte Reina Sofía, home to Picasso’s “Guernica.” Let us arrange a private tour with an expert art consultant as your guide.
- Nature and History in El Escorial
Take a picnic basket filled by the Four Seasons culinary team and drive 50 minutes northeast to El Escorial, home to historical attractions including the 16th-century Escorial Monastery, a UNESCO World Heritage Site. Enjoy nature at Bosque de la Herrería, where you can hike up to the Silla de Felipe II (the Chair of Phillip II, a rock that marks the summit of Machota Alta) for serene views. Further down in the park, have your picnic under the chestnut trees.
Four Seasons Hotel Madrid
Part of the Centro Canalejas Madrid – a collection of seven historical buildings beautifully combined into one – Four Seasons Hotel Madrid offers some of the city’s best views. With around 4,000 restored artefacts and a sunny rooftop restaurant and lounge, it’s an excellent base for road trippers exploring what makes Madrid such a vibrant European capital.