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Portugal's most stunning ancient towns by road

Portugal’s capital, Lisbon, enchants visitors with its wooden trams, melancholic Fado music and nightlife. It’s also the perfect base from which to explore some of Portugal’s most stunning ancient towns by road. We’ve picked five of the finest places to drive to.

Sintra

The Palace of Pena’s eclectic collection of buildings is perched in the Sintra Hills

The Palace of Pena’s eclectic collection of buildings is perched in the Sintra Hills

It should only take around half an hour to drive from Lisbon to the town of Sintra, where you’ll find winding alleys, romantic gardens and colourful palaces backed by emerald pines. Start in Sintra’s historic centre and head to the National Palace of Sintra, which was built on the site of a Moorish fortress and later transformed by King João I in the 15th century.

The Palace of Pena should also be on your itinerary. Perched in the Sintra Hills, its eclectic mixture of buildings is seen as one of the greatest examples of Romantic architecture. The gardens are similarly elaborate and contain over 500 species of tree. Stay at the Tivoli Palacio de Seteais, a luxurious five-star hotel in a former 18th-century palace.

Óbidos

You can walk around Obidos’ medieval walls to take in views of the town below

You can walk around Obidos’ medieval walls to take in views of the town below

The medieval walled town of Óbidos is an hour’s drive north of Sintra. It’s known as “the Wedding Gift Town” as it was the traditional gift from kings of Portugal to their queens. This tradition started in 1282 when King Dinis offered it to his new wife, Queen Isabel. It then became part of the Queen’s estate until the 19th century.

Start by strolling around its cobbled centre, among charming whitewashed houses with brightly coloured window boxes. Stop to admire the chapel in the town’s main gate, Porta da Vila, which has beautiful 18th-century tiles. Wander Óbidos’ walls to take in views of the town below and to reach its medieval castle, which is now a hotel. And before you leave, try the local cherry liqueur, Ginjinha, which is served in an edible chocolate cup – just agree on a designated driver first.

Tomar

The Convent of Christ overlooks the town of Tomar

The Convent of Christ overlooks the town of Tomar

A little over an hour’s drive inland northeast of Óbidos is the pretty town of Tomar, the former seat of the Order of the Knights Templar. One of Tomar’s major sights is the Convent of Christ, located inside the walls of Castle of Tomar, which overlooks the town and is considered to be one of the most beautiful monuments in Portugal. Visit the complex to see a combination of Romanesque, Gothic, Manueline, Renaissance and Baroque architecture – the elaborate Manueline Window is a particular highlight.

From the Convent of Christ, walk through the Mata dos Sete Montes woodlands to Tomar’s historic centre, dipping in and out of shops and perhaps stopping to try a Fatias de Tomar, a local sweet treat made with egg yolks and sugar. Stay at Hotel Dos Templarios which is set in gardens and has a lagoon-style pool.

Coimbra

Climb the Coimbra University tower for a 360-degree view of the city

Climb the Coimbra University tower for a 360-degree view of the city

An hour north of Tomar, via the A13, is the riverside city of Coimbra. It’s home to the oldest and one of the most highly esteemed universities in Portugal. Look around the university’s Baroque-style library, where two colonies of bats are kept to protect its books from insects. Then climb its tower, whose bells sound the beginning and end of classes, for 360-degree views.

The Monastery of Santa Cruz is also worth visiting, which is home to the tomb of the first king of Portugal. Its interiors are impressive, decorated with Baroque tiles, while the Baroque organ present is equally so. And if music’s on your mind, head later into Coimbra and enjoy a traditional, haunting Fado performance in the city. You’ll see this genre of music performed in the city’s bars after 10pm – but you can also catch a performance earlier in the city’s Fado Centre. Book into the central Sapientia Boutique Hotel.

Monsanto

Monsanto’s lanes have stone houses and boulders either side

Monsanto’s lanes have stone houses and boulders either side

Drive for around two and a half hours, towards the Spanish border, to reach the picturesque village of Monsanto. The red-roofed collection of buildings clings to the edge of a slope and the first thing to do is to climb up through Monsanto’s winding lanes, lined with stone houses and huge boulders. Keep going up a track and you’ll find the ruins of a castle that Alfonso the First gave to the Knights Templar, as well as beautiful views.

It’s then a three-hour (170-mile) drive back to Lisbon. Stay a night at the chic Hotel White Lisboa and relax in its rooftop swimming pool.