This time, we discovered a different side of Portugal. Leaving Lisbon behind, we set off by car for its quieter corners, through vineyards, olive groves, sweeping landscapes and small towns.
Along the way, we stayed at three hotels, each with its own story and distinctive character. First came a boutique hotel with its own winery in the Alentejo countryside, followed by a historic estate near Monsaraz and, finally, an intimate boutique retreat centred on wellbeing and gastronomy.
Together, these three properties make for a wonderful multi-day road trip. We recommend spending at least two nights at each, leaving plenty of time to explore the places in between.
Quinta do Paral
After landing in Lisbon, we collected our car and headed southeast towards Alentejo. This vast region covers almost a third of Portugal, yet remains one of its least populated areas. Towns gradually give way to open countryside, vineyards, olive groves, cork oak trees and little whitewashed villages. This is where our Portuguese road trip began.
Near the town of Vidigueira lies Quinta do Paral, a property that brings together a boutique hotel and its own winery. Winemaking is woven into the entire guest experience. The surrounding vineyards are more than a picturesque backdrop: they produce the wines guests can enjoy right where they were made.
The vision behind Quinta do Paral belongs to Dieter Morszeck, former president of RIMOWA and grandson of the brand’s founder. He came to Alentejo with a vision for his own winery and gradually developed a project that now includes a hotel. With just 22 rooms, the property retains an intimate atmosphere, allowing the landscape, wine and gastronomy to take centre stage.
Here, gastronomy and winemaking go hand in hand. The kitchen draws on seasonal, locally sourced ingredients, with dishes paired with wines produced on the estate. A stay can therefore include not only wine tastings but also a closer look at the winery and the way its wines are made.
From there, we continued across Alentejo. On the way to our next stop, there is one place well worth making time for: Évora.
Évora’s historic centre is a UNESCO World Heritage Site, bringing together traces of several periods of Portuguese history. At its heart, you will find a Roman temple, a medieval cathedral and the Capela dos Ossos, a chapel famous for an interior decorated with thousands of human bones. You do not need to stay overnight to explore the centre, making Évora an ideal stop along the way.
São Lourenço do Barrocal
After visiting Évora, we travelled farther east, almost to the Spanish border. Our next destination was São Lourenço do Barrocal, a more than 200-year-old estate near medieval Monsaraz.
The estate’s history dates back to the first half of the 19th century, when a substantial farming community began to take shape here. It was far more than a traditional farm. Barrocal operated as a small, self-sufficient village, home to as many as 50 families. Residents tended the fields, vineyards and livestock, while the estate also had a school, workshops and other facilities essential to everyday life.
More than two centuries later, the estate remains in the hands of the same family. Its current owner, José António Uva, represents the eighth generation and was the driving force behind its restoration. Buildings once occupied by farmworkers and their families have gradually been transformed into guest rooms and shared spaces, all while preserving the estate’s original character.
Farming did not disappear with the arrival of the hotel. The extensive grounds still encompass vineyards, olive groves, a vegetable garden and pastures with farm animals. Guests can gain a closer understanding of life on the estate, sample its produce or explore the surroundings on horseback.
With its animals and generous outdoor space, São Lourenço do Barrocal is also a wonderful choice for families with children. Younger guests have room to spend time outdoors, discover the surrounding nature and get to know the animals that are part of daily life on the farm.
Close by is Monsaraz, a small medieval hilltop town overlooking the surrounding countryside. Its whitewashed houses, narrow cobbled streets and ancient walls offer sweeping views towards Lake Alqueva and the wider Alentejo landscape. A few hours are enough to explore, so a visit can easily be included in one of your days at São Lourenço do Barrocal.
Quinta Filippa
From São Lourenço do Barrocal, we embarked on the longest drive of our journey, this time heading north. The route gradually leaves Alentejo behind and leads into central Portugal, where the final hotel of our road trip awaits.
Along the way, Óbidos is well worth a stop. Enclosed within medieval walls, the town is a maze of narrow cobbled streets, whitewashed houses with colourful details and a beautifully preserved castle. Its compact centre is easy to explore in a few hours, so there is no need to rearrange the rest of your itinerary.
We then continued towards the Leiria region, where Quinta Filippa occupies a 40-hectare estate. From the moment you arrive, it feels different from the previous hotels. Rather than a conventional hotel, it resembles a private country residence. In fact, the current owners originally envisioned it as a holiday home for their family. Over time, their plans evolved and the property became an intimate boutique hotel with just 16 rooms.
Wellbeing is central to the experience. The grounds feature a 25-metre heated saltwater pool, saunas and a steam room, complemented by activities such as yoga and meditation. Yet wellbeing here extends far beyond the spa. Movement, the surrounding natural landscape and, above all, food are equally important.
Dining at Quinta Filippa is a little different from what you might expect at a hotel. Instead of ordering from a traditional à la carte menu, guests are served a thoughtfully composed set menu that changes with the seasons and the ingredients available at the time. Some are grown on the estate, while others come from local farmers, fishermen and producers. Rather than choosing from an extensive selection of dishes, guests place their trust in the kitchen and the best of what the season has to offer.
Although Quinta Filippa is set deep in the countryside, the Atlantic is never far away. The coast is approximately a 15-minute drive away, making it easy to combine time at the hotel with a trip to the ocean in a single day.
Travelling by car gave us a different perspective on Portugal. Rather than moving between its best-known cities, we had the opportunity to discover regions that often remain off the main tourist routes.
Each hotel is also within reach of places worth visiting in their own right. Évora, Monsaraz and Óbidos fit naturally into the drives between properties, adding another dimension to the journey beyond the hotels themselves.
For a road trip like this, we recommend allowing at least two nights at each property. There is no reason to rush the route. Leaving room in your itinerary gives you the freedom to stop along the way, change your plans and experience Portugal beyond its most familiar destinations.