Begin the day with pick up from your Lisbon accommodations by a knowledgable private guide. Hop in a comfortable, private vehicle and start heading northeast, directly to the upper Alentejo region, almost all the way to the spanish border on a 2h drive. There, pay a visit to Castelo de Vide, a small yet picturesque town. Tour the town’s main castle and, if time allows, shop for local handicrafts in the nearby markets.
Next, head to the medieval village of Marvão on the top of the São Mamede mountain. Pass by what is considered to be the most beautiful Portuguese road on the way and stroll along the medieval streets inside the castle walls, stopping to see the village’s most important historical and cultural landmarks. Stop for lunch and chance to relax before continuing on.
After lunch, proceed to the remains of the Roman city of Ammaia and it's museum. Then drive by Niza, home of one of the most famous kinds of cheese of Portugal. On the way back to Lisbon, pass by the beautiful and natural monument of Vila Velha de Ródão. See where the Tagus River carved thourgh the mountains in a place known as Portas de Ródão. Your guide will return you to your hotel by 18:00.