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

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

Two people run on blue, rooftop running track, overlooking Lisbon

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.

featured offer
Lisbon Getaway – 15% Off

Experience the best of Lisbon with 15% off our Room Rate.

Hotel staff walks along edge of indoor swimming pool deck
  • offer valid for: Sep 23 2021 – Dec 31 2022
  • minimum stay: 2 nights maximum stay: 12 nights


  • 15% off our Room Rate
more details
Let us help you plan your Lisbon experiences. 351 (21) 381-1400 Contact
  • A woman wearing a black and white salsa dancing dress and red flower in her hair dances with her face turned away from the camera
    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.

  • A young couple picnics under a large oak tree
    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.

Bright Four Seasons Terrace Suite with king bed with white linens and beige headboard, beige walls and curtains, patio doors and view of sunny terrace

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.

featured offer
City Escape

Enjoy 15% off our Room Rate.

Monument to Alfonso XII beside water, with statue of man riding horse, lions
  • offer valid for: Sep 23 2021 – Sep 27 2021 Nov 1 2021 – Mar 31 2022
  • minimum stay: 2 nights maximum stay: 31 nights
  • Reservation must be made at least 3 days in advance


  • 15% off our Room Rate
more details
Let us help you plan your Madrid experiences. +34 910 883 333 Email Us

Inspiration From Fellow Travellers

  • @wisteria_voyage
  • @mbeltri

Ready to take the scenic route?

Reserve your stay at Four Seasons and start planning your road trip today.