Road Trip: Ten Charming Stops Between Madrid and Lisbon
- The editorial team
- Oct 19
- 8 min read
Updated: Oct 21
The road between the two capitals holds secrets that flights will never reveal.
While airlines shuttle travellers between Madrid and Lisbon in just over an hour, choosing the overland route, you discover a different Iberia altogether. This 600-kilometre journey through Spain's Extremadura and Portugal's Alentejo regions traces ancient trade routes and forgotten frontiers, revealing the layered history that shaped the Iberian Peninsula.
Pack your curiosity along with your luggage: the small towns between these two great cities offer rewards that no itinerary can rush. For your road trip from Madrid to Lisbon, here are ten towns worth exploring along the way:
Trujillo, Spain
250 km (155 miles) from Madrid | 415 km (258 miles) from Lisbon
This medieval hilltop town showcases the stunning Plaza Mayor surrounded by palaces and the imposing castle where conquistador Francisco Pizarro was born. The historic quarter feels frozen in time.
What to see and do
Climb to the 9th-century Moorish castle for panoramic views across the Extremaduran plains. Explore the Plaza Mayor, one of Spain's most spectacular squares, dominated by an equestrian statue of Pizarro. Visit the Palacio de la Conquista with its ornate corner balcony, and the Iglesia de Santa María la Mayor, a Gothic-Renaissance church housing a magnificent altarpiece. Don't miss the atmospheric Jewish quarter with its narrow cobbled lanes. Time your visit for early evening when storks return to nest on church towers and the setting sun bathes the honey-colored stone in golden light.
Caceres, Spain
300 km (186 miles) from Madrid | 365 km (227 miles) from Lisbon
A UNESCO World Heritage site with one of Europe's best-preserved medieval quarters. Wander through cobbled streets past Renaissance palaces, ancient towers, and atmospheric stone archways.
What to see and do
Enter the old town through the Arco de la Estrella and lose yourself in the Ciudad Monumental, where filming for Game of Thrones took place. Climb the Torre de Bujaco for city views, then explore the Casa de las Veletas, built atop a Moorish cistern with stunning horseshoe arches. The Casa-Museo Árabe Yusuf Al Burch offers insight into the city's Moorish past. For contemporary culture, check out the Museo Helga de Alvear, which houses an extensive contemporary art collection. Sample local jamón ibérico and Torta del Casar cheese at traditional tabernas around Plaza Mayor.
Merida, Spain
340 km (211 miles) from Madrid | 325 km (202 miles) from Lisbon
Home to Spain's most impressive Roman ruins, including a magnificent theatre, amphitheatre, and aqueduct. This former Roman capital offers a fascinating glimpse into ancient Iberian life.
What to see and do
The Roman Theatre, still used for summer performances, is one of the best-preserved in the Roman world with its elaborate two-story scaenae frons. Walk through the adjacent amphitheatre where 15,000 spectators once watched gladiatorial combats. Cross the Puente Romano, a 792-meter bridge spanning the Guadiana River—one of the longest surviving Roman bridges. Explore the Casa del Mitreo with its intricate mosaics, and the Temple of Diana, remarkably preserved in the town centre. The Museo Nacional de Arte Romano, designed by Rafael Moneo, houses an extraordinary collection of Roman artefacts. Don't miss the Acueducto de los Milagros, whose towering brick arches reflect beautifully in the surrounding pools. If visiting in summer, catch a classical theatre performance in the ancient Roman Theatre.
Zafra, Spain
390 km (242 miles) from Madrid | 275 km (171 miles) from Lisbon
Known for its whitewashed buildings and Moorish influence. The arcaded Plaza Grande and medieval castle-turned-parador make it a picturesque lunch stop.
What to see and do
Begin at the interconnected Plaza Grande and Plaza Chica, the town's vibrant heart, surrounded by elegant arcades ideal for a coffee break. Visit the Alcázar, a 15th-century castle now operating as a luxurious parador hotel—non-guests can tour the stunning Renaissance courtyard and chapel with its beautiful painted ceiling. The Colegiata de la Candelaria features an impressive Zurbarán painting collection. Wander through the atmospheric whitewashed streets of the old town, discovering hidden plazas and wrought-iron balconies overflowing with geraniums. If visiting on Tuesday or Saturday, be sure to experience the lively outdoor market. Sample local cuisine at traditional restaurants serving caldereta extremeña (lamb stew) and regional wines from nearby Tierra de Barros.
Olivenza, Spain
430 km (267 miles) from Madrid | 235 km (146 miles) from Lisbon
A border town with a unique Portuguese character despite being in Spain. Its distinctive architecture and fortifications reflect centuries of cultural blending between the two nations.
What to see and do
Explore the remarkably intact fortifications, including the castle keep with its ethnographic museum showcasing the region's Portuguese-Spanish heritage. Walk the medieval walls offering views across the border plains toward Portugal. Visit the Igreja de Santa Maria Madalena, a stunning example of Manueline architecture, rare in Spain, with its twisted columns and nautical motifs. The Igreja da Misericórdia features beautiful azulejo tilework typical of Portuguese churches. Stroll through streets lined with Portuguese-style architecture, white-and-yellow painted houses, and decorative tiles. Browse the Museo González Santana to see works by this local artist. Sample the unique local gastronomy that blends Spanish and Portuguese traditions—try açorda alentejana and local pastries at cafés around Praça da República.
Elvas, Portugal
445 km (276 miles) from Madrid | 220 km (137 miles) from Lisbon
Another UNESCO site boasting the world's most extensive bulwarked dry ditch fortification system. The star-shaped fortress and impressive aqueduct dominate this frontier town.
What to see and do
Walk through the massive star-shaped fortifications, including the Fort of Santa Luzia and Fort of Graça, engineering marvels that demonstrate 17th-century military architecture. Climb the castle keep for panoramic views of the defensive works. Marvel at the Amoreira Aqueduct, stretching over seven kilometres with its distinctive multi-tiered arches built over 120 years. Explore the historic centre's cobbled streets, visiting the Cathedral with its Manueline doorway and the octagonal Igreja de Nossa Senhora da Consolação lined with 17th-century azulejos. Browse the boutiques selling traditional Alentejo handicrafts. Savour Alentejo cuisine at local restaurants—try açorda de bacalhau, ensopado de borrego, and ameixas d'Elvas (candied plums), the town's sweet speciality.
Estremoz, Portugal
410 km (255 miles) from Madrid | 165 km (103 miles) from Lisbon
Famous for its marble production and imposing medieval castle. The upper town offers commanding views while the Saturday market bursts with local pottery and crafts.
What to see and do
Ascend to the upper town (Cidade Alta) to explore the medieval castle complex with its striking marble Torre das Tres Coroas—climb the tower for sweeping Alentejo views. Visit the palace within the castle walls, now a pousada, to admire the marble chapel and royal chambers. In the lower town, browse the Saturday morning market in Rossio Marques de Pombal, one of Portugal's most authentic country markets, where farmers sell produce, pottery, and traditional crafts. Discover local pottery workshops producing distinctive clay dolls and ceramics. Explore the marble quarries and showrooms to discover why Estremoz marble adorns palaces worldwide. Visit the Museu Municipal for regional archaeological finds and traditional Alentejo life exhibits. Sample local wines and robust Alentejo dishes like migas and carne de porco à alentejana.
Evora, Portugal
400 km (249 miles) from Madrid | 130 km (81 miles) from Lisbon
Perhaps the most essential stop, this UNESCO World Heritage city features a Roman temple, medieval Cathedral, bone chapel, and atmospheric streets within well-preserved walls.
What to see and do
Begin at the Temple of Diana, one of the Iberian Peninsula's best-preserved Roman structures, with its Corinthian columns standing for nearly 2,000 years. Visit the imposing Sé Cathedral, Portugal's largest medieval Cathedral, and climb to the rooftop for city views. Experience the haunting Capela dos Ossos (Chapel of Bones), its walls lined with thousands of human bones arranged in decorative patterns—a memento mori masterpiece. Explore the former Royal Palace, now housing contemporary art exhibitions, and the Igreja de São Francisco with its Manueline portal. Wander the labyrinthine streets, discovering hidden plazas, Renaissance fountains, and Moorish-influenced architecture. Browse artisan shops selling cork products, ceramics, and textiles. Enjoy traditional Alentejo cuisine at local tascas—order peixinhos da horta, açorda, and pastéis de toucinho while sampling full-bodied regional wines from nearby vineyards. Allow at least half a day to explore this cultural treasure.
Arraiolos, Portugal
380 km (236 miles) from Madrid | 110 km (68 miles) from Lisbon
Renowned for its handmade wool carpets with a centuries-old tradition. The circular castle ruins overlook this charming village, where artisan workshops welcome visitors.
What to see and do
Visit the hilltop castle ruins, a circular fortress dating to the 14th century, offering panoramic views over the Alentejo countryside dotted with cork oaks and olive groves. Tour workshops where artisans continue the 500-year-old tradition of creating Arraiolos carpets—distinctive embroidered wool rugs with Persian and Moorish influences, each taking months to complete. Watch craftspeople at work and purchase authentic pieces from local ateliers. The Interpretive Centre of Arraiolos Carpet explains the history and techniques of this unique art form. Stroll the peaceful village streets lined with whitewashed houses decorated with colourful borders. Visit the Igreja do Salvador with its Manueline portal. Browse shops selling local honey, olive oil, and handicrafts. Enjoy a leisurely lunch at a traditional restaurant serving hearty Alentejo fare in this tranquil setting.
Montemor-o-Novo, Portugal
360 km (224 miles) from Madrid | 90 km (56 miles) from Lisbon
A peaceful town crowned by castle ruins offering panoramic Alentejo views. Stop here for authentic Portuguese cuisine before the final stretch to Lisbon.
What to see and do
Hike or drive up to the impressive castle ruins perched dramatically on a hilltop—the medieval walls and towers provide spectacular 360-degree views across cork forests and rolling plains. Explore what remains of the royal palace where King João II died in 1495. Visit the Igreja Matriz with its Manueline doorway and azulejo-lined interior. Discover the Convento de Nossa Senhora da Saudação, a beautifully restored 16th-century convent. Wander through the historic centre's quiet streets, admiring traditional Alentejo architecture and stopping at small cafés.
The town is known for its olive oil production—visit local producers or shops selling premium azeite. Enjoy an authentic Alentejo meal at family-run restaurants serving dishes like ensopado de borrego, sopas de tomate, and sericaia (egg pudding) for dessert. This peaceful town offers a perfect final taste of rural Portugal before reaching the bustling capital.
General Travel Advice
Both Spain and Portugal are welcoming, safe destinations with excellent infrastructure for travellers. English is widely spoken in major cities and tourist areas. The siesta tradition remains strong in smaller towns—expect shops and restaurants to close between 2pm and 5pm, though this varies by region and is less common in larger cities.
Tipping practices are modest compared to North America. In restaurants, rounding up the bill or leaving 5-10% for good service is standard. Taxi drivers appreciate rounding up to the nearest euro. Service charges are typically included in restaurant bills.
Driving Tips for Car Rentals
An international driving permit is not required for US, Canadian, EU, UK, or Australian license holders, though having one can be helpful if stopped by police.
Driving Regulations: Drive on the right side of the road in both countries. Speed limits are typically 120 km/h on motorways, 90-100 km/h on rural roads, and 50 km/h in towns, though limits vary and are well-signposted. Speed cameras are common. Both countries have strict drink-driving laws, and enforcement is rigorous.
Seatbelts are mandatory for all passengers. Using mobile phones while driving is illegal without a hands-free system. Right-of-way rules at roundabouts follow standard European practice—yield to traffic already in the roundabout.
Parking: Historic town centres often have restricted vehicle access or pedestrianised zones. Look for designated parking areas on the outskirts of old towns—many are free or inexpensive. Blue painted parking spaces typically require payment during business hours; white painted spaces are usually free. Never park in yellow-marked zones, which are reserved for residents or specific uses.
Border Crossing: Travelling between Spain and Portugal within the Schengen Area requires no border controls or passport checks, though carry your passport and driver's license at all times. The currency changes from euro to euro, making the financial transition seamless.
Fuel Stations: Fuel stations (gasolineras in Spain, bombas de gasolina in Portugal) are common along major routes, though less frequent in rural areas. Fill up when passing through larger towns. Most stations are self-service, and credit cards are widely accepted, though some rural stations may be cash-only or closed on Sundays.
Safety and Emergencies: Both countries have excellent emergency services. The pan-European emergency number is 112 for police, ambulance, or fire services. Keep your rental agreement, insurance documents, and emergency contact numbers readily accessible. Vehicle break-ins can occur at tourist sites—never leave valuables visible in your car, and use hotel parking when available.
