Charming Costa de Lisboa and rural Alentejo | Portugal Itinerary

Route

This itinerary starts on the Costa de Lisboa with two nights in Cascais, close to Sintra and the Atlantic coast. You then travel inland to the Alentejo with three nights around Évora. From there you explore historic towns such as Monsaraz, Vila Viçosa, Elvas and Estremoz. The final stage takes you to the region around Santiago do Cacém and the Estuário do Sado nature reserve before returning to Lisbon.

Pace

A varied pace with three stays. Two nights on the coast, three nights in the Alentejo countryside and two nights in the southern part of the region. This allows you to combine culture, nature and coastline without long driving distances.

Highlights

The seaside town of Cascais and the palaces of Sintra, the historic city of Évora with its white houses and Roman temple, and the fortified villages of the Alentejo such as Monsaraz. You also discover the marble towns of Estremoz and Vila Viçosa, the Roman ruins of Miróbriga and the Estuário do Sado nature reserve.

Accommodation

You stay in carefully selected Caractère hotels: first on the Costa de Lisboa, then in the Alentejo among vineyards and cork oak forests, and finally in a peaceful hotel near Santiago do Cacém.

Profile

For travellers who want to discover both the Atlantic coast and the quiet countryside of the Alentejo. Ideal for combining nature, historic towns and local gastronomy.

Day 1: Departure to Lisbon - Cascais

You land at Lisbon airport, where you will pick up your rental car. In Cascais, you will stay 2 nights at a Caractère hotel. Get to know this elegant seaside resort.

Day 2: Costa de Lisboa - Sintra

Along the beautiful coastline, via Cabo da Roca and Praia do Guincho, to Sintra, the favourite residence of Portuguese princes, nobility and bourgeoisie for 600 years. Estoril and Cascais are 2 famous and lively seaside resorts with sandy beaches and beautiful villas.

Day 3: To the unspoilt Alentejo

Depart for Évora or surroundings, where you will stay 3 nights. Monsaraz is a pretty fortified village perched on a high cliff with stunning views and unique sunsets.

Day 4: Évora

Definitely one of Portugal's most beautiful cities: a walled town with winding Moorish alleys with arches, brilliant white houses with terraces and flowers, palaces from the Middle Ages and Renaissance, and a particularly cosy atmosphere.

Day 5: Redondo - Vila Viçosa - Elvas and Estremoz

Get to know the untouched nature of Alentejo as well as historic towns: Redondo, famous for its red wine and typical pottery, Vila Viçosa, where dukes and kings often stayed and Elvas, a few kilometres from the Spanish border, with its city wall and aqueduct. On the way back, you will pass through Estremoz, between marble quarries and a Vauban-style city wall, to Évoramonte, beautifully situated on a hill.

Day 6: To Santiago do Cacém or Grândola

Depart for Santiago do Cacém, where you will meet the Roman ruins of Miróbriga in a beautiful green setting.

Day 7: Alcácer do Sal + Estuário do Sado natural park

This is where everything revolves around salt, cork and rice. The salt flats and rice fields surrounded by forests of cork oaks are still visible. The Reserva Natural do Estuário do Sado is an impressive nature reserve of more than 23,000 ha.

Day 8: Going home

Return your rental car at Lisbon airport and fly back home. Prefer to stay a little longer? Caractère will take care of it!

Frequently asked questions about the elegant Costa de Lisboa and the rural Alentejo

What is the best time for this itinerary?

April to June and September to October are ideal. The weather is pleasant for visiting both the coast and the historic towns of the Alentejo.

Do you need a rental car for this trip?

Yes. The different regions are spread out and a rental car makes it easy to reach places such as Sintra, Monsaraz, Estremoz and Santiago do Cacém.

What makes the Alentejo so special?

The Alentejo is known for its white villages, vast landscapes and cork oak forests. Historic towns such as Évora and Monsaraz give the region a very distinctive character.

Is this trip more about nature or culture?

The itinerary combines both. You explore palaces and historic towns, but also natural areas such as the Estuário do Sado and the open landscapes of the Alentejo.