Road trip among villages and castles in Portugal

For a unique holiday travel back in time and follow our itinerary among villages and castles in Portugal.
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If you are found of medieval history, castles, old walls, and villages perched on the top of a hill, then you should choose Portugal as your next holiday destination.

Around Lisbon there are many traces of the past surrounded by beautiful landscapes, which are often ignored by tourists.

The itinerary between villages and castles in Portugal is a dreamy tour through some famous locations and some less known attractions. During you 10 days trip you will feel like going back in time and be the main character of a fairy tale; kings and queens, dames and knights, ready to protect their pride and their land.

Daydreaming is part of the game… if you are ready to dive into a past full of history, book your flight ticket today.

Itinerary map and information

Here comes the map of the itinerary among villages and castles in Portugal; we recommend to move by car. You can rent one at Lisbon airport.

Itinerary: 1100 km | Duration: 10 days | Best time: from May to September

First day: Lisbon

The Alfama district

Our itinerary starts in Lisbon, the charming capital of Portugal. The best way to start your holiday is to have a coffee at one of the many cafes in the Baixa district, maybe at one of its elegant squares like Rossio or Commerce Square. Take it easy and enjoy being in one of the most beautiful cities of Europe.

The first thing that we recommend to do is going on a city tour aboard the historical tram 28, which goes around the narrow streets of Lisbon, passing through the charming districts of the Portuguese capital city. The image of the piercing white and yellow wooden carriages of the tram going up and down the city represents one of the most famous images of the city.

After lunch it is time to visit one of the most traditional districts of Lisbon, Alfama. Located between a hill and the river, it is the most authentic area of the city where time seems to be suspended.

Start your visit around Alfama from São Jorge Castle, which originally was a defensive fortress and then it was used as a royal palace. Its tree-lined alleys are perfect for a romantic walk, while its terrace is the best panoramic viewpoint of the city; you will see a multitude of roofs from the Alfama and in the background the Tagus River, the undisputed protagonist of Lisbon’s history.

Once you have finished your visit to the castle, stay in the Alfama and stroll around the area; the best thing to do in these cases is to get lost, as every corner is full of surprises and emotions. Our only tip is to watch the sunset from the Miradouro de Santa Luiza, located next to the Santa Luiza church.

Stay in the area for dinner; here you will find several traditional restaurants. The Alfama district is perfect to see a fado concert, the traditional Portuguese music.

Second day: Lisbon

The Monument to the Discoveries in Belem

On your second day keep discovering the main areas of Lisbon, that is to say Baixa, Chiado and the Bairro Alto. Do not miss a visit to the Carmo Convent, a gothic church that was severely damaged during the earthquake of 1755. Today only the facade of the convent has survived, while the roof was replaced by the sky.

Spend the afternoon discovering the Belém district, located along the shore, a few kilometers from the center. Don’t miss the iconic Belém Tower, a majestic defensive tower built along the river, as well as the impressive Monument to the Discoveries, a huge stone caravel built to celebrate the maritime ventures of Portugal.

The third attraction you can’t miss in Belém is the magnificent Mosteiro dos Jeronimos, made of yellowish stone contrasting with the blue of the sky and rich with Manueline decorations. Vasco da Gama was buried here.

Before going back to the city center make a stop at the Antiga Confeitaria de Belém, the most famous pastry shop of Lisbon, to taste the delicious pasteis de nata.

At night you can choose to stay in the Baixa or to enjoy the nightlife of Bairro Alto. However, before it gets too late, visit the Elevador de Santa Justa, an architectural jewel from which you can admire the city and the castle: an extraordinary view.

Tips on the Lisbon itinerary

Do you want to study an alternative 2 or 3 days itinerary in Lisbon? Check our One week itinerary in Lisbon and surroundings

To plan your visit to Lisbon, read more below.

Lisbon guide Accommodation in Lisbon

Third day: Évora, Estremoz and Vila Viçosa

The Giraldo Palace in Evora

It is time to take the car and leave Lisbon behind and start discovering the wonders of the Alentejo, an inland Portuguese area which is still far from the beaten path.

Inland villages are usually very small and it is possible to visit more than one in a day. The first stop to discover the ancient beauties of Portugal is Évora, the best preserved city of the country.

Located at the top of a hill, Évora is a charming city boarded by perfectly preserved walls from the 14th century. Around the old city it is possible to admire several traces of its past, including a medieval cathedral, monasteries, and the ruins of a Roman temple.

Évora is also home to a prestigious university and it is the gastronomical capital of the region; try some typical dishes from the Alentejo region at one of its several traditional restaurants.

Estremoz, the next stop along our itinerary, has a medieval castle. However, this place is specifically famous for the precious marble that is extracted in its surrounding area, whose quality can be compared to the one of Carrara marble. It is used to build palaces and even streets. Alentejo’s marble has turned Estremoz into a treasure not to be missed.

Keep your tour exploring another village famous for its shining marble, that is to say the elegant Vila Viçosa, which used to be home to the dynasty of the Bragança family. Discover the secrets of kings and queens visiting the elegant Paço Ducal.

Accommodation in Evora

Fourth day: Elvas, Campo Maior and Sortelha


Take the car and drive to Elvas, a city at the border with Spain. Inside an impressive defensive network made of solid walls, towers and ditches, there is a well preserved city with a lovely square, a couple of interesting museums, and narrow streets that remind of an Arab medina. You may be one of the few tourists around as there are not many people coming here.

Head north towards Campo Maior, a lovely town whose name reminds of its Roman origins. According to the legend, it was founded by three families who decided to get together to create a village and help each other.

The last stop of the day is Sortelha, famous for its fortified castle from the XII century, perched on the top of a hill.

Accommodation in Sortelha

Fifth day: Belmonte, Guarda, Sabugal and Linhares da Beira

Belmonte Castle

The  fifth day of our itinerary includes four stops; however, as every village is very small, you won’t have to be on a rush in order to see them all.

Take you time and whenever you are ready head to Belmonte, the birthplace of Pedro Álvares Cabral, the explorer regarded as the discoverer of Brasil. Here you can admire a majestic castle made of granitic stones and the testimonies of the Jewish community of the Bairro dos Marrocos, outside the castle walls.

Along the way to Guarda – our next stop – look to your left side to see the Centum Cellas Tower, a peculiar construction whose origins are still unknown.

Perched on one of the slopes of Serra do Estrelha, Guarda, Portugal’s highest town, keeps its original charm and it surely deserves a visit. According to a popular description, Guarda is “strong, rich, loyal, and beautiful”. Make a stop here to see if it is true.

Sabugal is one of the best preserved castles of Portugal located in a lovely village along the shore of the river Coa; make a stop to visit the castle and enjoy the magnificent panoramic view from above.

Another castle that deserves a visit is the one of Linhares da Beira. However, if you have had enough of seeing castles, stroll around the old center to admire a mix of architectural styles of different ages.

Sleeping in Guarda Accommodation in Sabugal

Sixth day: Castelo Rodrigo, Trancoso and Viseu


Start your sixth day discovering some of the most charming villages of Portugal, Castelo Rodrigo, located at the top of a hill and overlooking the valley that extends north to the Douro region and east to Spain.

A stop for pilgrims along the path to Santiago de Compostela – probably even Saint Francis of Assisi stopped here – Castelo Rodrigo deserves a visit for its stone houses and the suggestive landscape that surrounds it. An interesting and peculiar attraction to see is the Pelourinho, a Manueline style pillory pole.

The next stop along our itinerary is Trancoso, a city famous for bringing bad luck to Portuguese kings; according to the legend, a local story teller foresaw the end of the monarchy, which happened soon after the death of Dom Sebastião.

The marriage between D. Dinis and Isabella of Aragon took place in this little town that managed to preserve its medieval atmosphere.

Spend the night in Viseu, a charming city in the Beira region, famous for its great Dão red wines.

Accommodation in Viseu

Seventh day: Aveiro and Coimbra

The landscape of Coimbra

On the seventh day leave early as there are many attractions to see.

The first stop is Aveiro, an elegant city located between the sea and the lagoon, crossed by several canals. Enjoy a relaxing break on a river cruise on a moliceiro, the traditional boats from Aveiro that in the past were used to collect seaweeds.

As you get off the boat, stroll around the city center, which is rich with elegant art nouveau palaces; if you are interested in this architectonic style, you can learn more about it at the Museu de Arte Nova.

The second stop is the beautiful city of Coimbra, which became famous all over the world thanks to its old university. The historic headquarter of the university, located in the upper part of the city, is an attraction not to be missed: its elegant and austere palaces, built around the Páteo das Escolas, are dominated by a majestic tower that marks the rhythms of the academic life.

It is worth to pay the ticket to visit the Joanina Library, where there are more than 300 thousand volumes from the XVI and the XVIII century.

Spend the rest of the day exploring the other attractions of Coimbra, like the Santa Clara Monastery in Velha and at night enjoy the lively atmosphere of this university city.

Accommodation in Coimbra

Eight day: Obidos and Tomar


Leave the city behind and travel back in time visiting Obidos, another traditional medieval town boarded by defensive walls. The castle today is home to a luxury hotel and it is still possible to walk along the city walls. From here you can enjoy a beautiful view abovw the village and its surrounding landscape.

You can’t not miss a stop to visit Tomar, the old seat of the Templars. Its main attraction is the Convent of Christ, a jewel of Renaissance architecture. From here you can walk to the city center.

Accommodation in Tomar

Ninth day: Sintra

The Palacio da Pena in Sintra

On your ninth day you will make only one stop, not just because you are going to visit a beautiful destination but also because it has so many attractions to see that it deserves a whole day, or even more.

The fairy Sintra is a real gem surrounded by the extraordinary landscape of the Sintra-Cascais Natural Park; it is decorated by eccentric palaces and villas built by kings and intellectuals who fell in love with the area.

The most famous one is the iconic Palacio da Pena, characterized by a decadent charm, pastel pink and yellow walls, and perched on the top of a hill from where you can see a breathtaking view over the ocean.

Other Sintra’s attractions include the Palacio Nacional, or Palacio da Vela, the Quinta do Regaleira, the Castelo dos Mouros and the Convento dos Capuchos.

Accommodation in Sintra

Tenth day: Sintra and return to Lisbona

The lighthouse of Cabo da Roca

Your last day has a relaxed program as it depends on your flight schedule.

If you have enough time stop at Cabo do Roca, the westernmost point of Europe. A promontory overlooking the ocean surrounded only by a small cafe and a lighthouse. A very unique view that will make you feel at the edge of the world.

Once you are back to Lisbon, spend your last hours shopping on the elegant Rua do Augusta or Rua Garrett; if you have the whole day, visit the Park of Nations; after spending so many days visiting romantic medieval villages, going around the modern area of the city – which was built on Expo ’98 – will make you feel like traveling in time.

Do you prefer diving into the past until the end of your holiday? Visit the Lisboa Story Centre, a museum about the charming history of the city of Lisbon.
















Cabo da Roca

Cabo da Roca