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Alentejo Tour - visiting charming castles route

Tour Alentejo Castles, Portugal

The Tour Alentejo Castles is the perfect way to get to know the history of Alentejo, alive still today in its fortifications, which defended the territory from potencial invaders from the top of the hills. But the itinerary we present you here will also show you the beautiful Alentejo landscape as far as the eyes can see while we follow the roads which lead to several fortified cities and villages.

Our guided tour in Alentejo takes you on a road trip to explore castles built hundreds of years ago but where, still today, people live proud of their land. For this reason, the tour is perfect for those who want to find a historic Alentejo route visiting important monuments in Portugal but also finding the nice and welcoming people of the southern region.

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Alentejo Tour – take a peek from this window

If you only have one day to get familiar with this part of Alentejo, such an itinerary is ideal for you. Join us! Together, we will do the circuit at our own pace, with a guide who is also a knowledgeable travel companion. We present you the Alentejo which you have always heard about and explain, on spot, the legacy of its History and culture.

Itinerary Tour Alentejo Castles

Évora – Arraiolos – Evoramonte – Estremoz – Borba – Vila Viçosa – Alandroal – Redondo – Valongo – Return to the starting point

Circuit of around 105mi / 170km

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Alentejo Tour Circuit Map

Tour Alentejo Castles – stops and highlights

Although there is much to do and see in all these villages and cities in Alentejo, this tour is destined to show you mainly the castles. You will now see our route a little more detailed so that you can have the notion of what you are going to see.

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Alentejo fields from the top of Evoramonte Castle

Evora Castle

In Evora, UNESCO world heritage, we visit part of the three walls which protected it in different times. Inside them, Romans, Visigoths and Arabs took shelter. The first king of Portugal, King Afonso Henriques, conquered them… and the Muslims took the city back until the famous Geraldo Sem Pavor (Fearless Geraldo) reconquered them in 1165.

Later walls were built to protect the court of Portugal, which was in Evora for a while. In the 17th century, some remodelling and modernisation brought towers, doors and walls which are still part of the city inhabitants present daily routine.

Arraiolos Castle

This castle was built during the reign of King Dinis, around 1310, and a few years later was donated to Dom Nuno Álvares Pereira, to whom was given the title of Count of Arraiolos. The fortification was remodelled during the times of the Restauração da Independência (Restoration of Independence) but was later abandoned and suffered severe damage in the 1755 earthquake.

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Alentejo Tour – Arraiolos Castle

The classification as National Monument, in 1910, would bring restoration works. The Arraiolos Castle is quite original, since it’s surrounded by an elliptic-shaped wall, from where you can see the Alentejo fields for miles around.

Evoramonte Castle

We know of the Evoramonte Castle (or Evora Monte) only around 1160, when the christian reconquest was taking place. This was the domain of the constable Dom Nuno Álvares Pereira, distinct figure in the Portuguese history. An earthquake in 1531 made the reinforcement of the walls mandatory. The structure was then made similar to the style of the castellated palaces of the Renaissance.

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Alentejo Tour – Evoramonte Castle

In 1834, Evoramonte castle would be the chosen place to sign the Convention of Evoramonte, granting victory to Dom Pedro in the civil war between absolutists and liberals. The castle is still today part of the House of Bragança. The Tower at the highest part of the hill, corresponding to the Ducal Palace, is its trademark.

Estremoz Castle

Estremoz Castle was build in the 12th century, even though there must have been some sort of fortification since Roman times. It changed hands between Christians and Muslims until the reign of King Sancho II. Back then, there were reconstruction work. Later, under King Dinis, the Royal Palace was also built.

Many prominent figures of the history of Portugal have been in Estremoz Castle. Queen Saint Isabel passed away here, where she would have done the miracle of the roses. Dom Nuno Álvares Pereira made the castle his headquarters. Kings João I and Afonso V held court meetings. It was also at this venue that, in 1497, King Manuel handed Vasco da Gama the command of the fleet that would arrive to India.

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Alentejo Tour – Estremoz Castle

As for the fortification itself, an explosion in the ammunition deposit destroyed most of it in 1698. With the reconstruction, in 1740, King João V had the magnificent Arms Room built, which would be later plundered during the French Invasions in 1800. Nowadays, the old Royal Palace is used as an historic inn, partially open to visitors. Nearby, we find a statue of the Queen Saint Isabel, from where we see Serra d’Ossa from afar.

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Alentejo Tour – View from Estremoz Castle

Vila Viçosa Castle

The history of this place, one of the most important of the Tour Alentejo Castles, is long. Vila Viçosa was conquered to the reign of Portugal in 1217, after centuries of Roman and Muslim occupation. In the 14th century, Vila Viçosa Castle was built by order of King Dinis. It was later improved by King Fernando I.

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Alentejo Tour – Vila Viçosa Castle

As gratification for the services rendered during the crisis of 1383-1385, King João I offered it to Dom Nuno Álvares Pereira. A few years later, in 1422, the Dukes of Bragança ordered the construction of the castle palace. These new owners would come to have the village as the headquarters of the Duchy of Bragança, the greatest in the Iberian Peninsula under the Spanish Filipino domain. With the rise to the throne of King João IV, previously João II Duque of Bragança, Vila Viçosa lost some importance but became the royal residence during the holidays.

As for the castle, it took exclusive military functions from the 14th century. For that, some profound alterations were held. Its design became one of a gunner castle, something unique in Portugal. During the Restoration period, the fortification was adapted to the defensive needs of the time by adding a polygonal star system and reinforcing the citadel walls. It would again be reinforced in 1662.

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Alentejo Tour – Vila Viçosa Castle Castle interior

In the 30s/40s of last century, the walls went through new renovation works and, from then forth, some others were held by the House of Bragança Foundation. In the interior of Vila Viçosa Castle, we can see the Main Church, the Museum of Archeology and the Museum of Hunt. One of the doors has a view over the beautiful República Square, the most important of the village.

Alandroal Castle

The village of Alandroal was founded in 1298, during King Dinis’s reign. Regarding the castle, a National Monument since 1910, there is little information. Its small size gives it some charm, with particular reference to the towers and the door with marble from the region.

Redondo Castle

Redondo, land of wine and pottery, probably owes its name to the round rock found inside its primitive medieval walls. The village had administrative formation in 1250 through the charter granted by King Afonso III. But it was King Dinis who ordered the construction of the Castle of Redondo, of which six towers are still left. Two of them are the protection of the Ravessa Door, which gave name to a notorious Alentejo wine (Porta da Ravessa).

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Alentejo Tour – Redondo Castle

Valongo Castle

Valongo Castle has a muslim origin and its conquest supposedly happened shortly after Évora’s (1165). It was rebuilt in the 15th century. This was when the Torre de Menagem (keep) was added. Part of the attraction of this castle which is part of our tour in Alentejo is its location, isolated in the middle of farming fields and near a small lake.

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Alentejo Tour – Valongo Castle

Tour Alentejo Castles, Portugal – Prices and terms

Prices (per vehicle) The tour is private. We do not mix clients from different groups.
From 260€ on a 7-seat or 8-seat van
From 325€ on a historic classic car (up to 4/5 people)

These are some of our 30+ cars, each periodically available to take you on the Alentejo Castles Tour!

  • Our tours are private and can be altered according to your preferences
  • All visits are accompanied by a local guide speaking in English, French, Spanish or Portuguese
  • It is possible to start the tour in Lisbon or another village in Alentejo (request a quote)
  • The route is held by a tour operator partner of Visitevora, to whom we associated because we consider it the best option in this kind of tours

Fill in the contact form to book, ask us questions or suggest another tour in Alentejo.

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