On my recent trip, I visited one of Portugal’s hidden gems, the Alentejo region. Located in south-central Portugal, it's known for gorgeous rolling fields, cork oak forests, olive groves, and vineyards. Though it's an easy hour-and-a-half drive from Lisbon, it feels like a world apart. The slower pace allowed me to unwind and savor the experience, from visiting wineries to enjoying excellent meals and even biking through the countryside.
A highlight was visiting the city of Évora, the capital of Alentejo and a UNESCO World Heritage site with its Roman temple. Its well-preserved old town is still partially enclosed by medieval walls. Alentejo has rich artistic traditions, too, which I learned more about at a traditional pottery workshop.
Alentejo is wine country, and I stayed at two historic wine estates. The Convento do Espinheiro in Évora is a former 15th-century convent converted into a five-star hotel. It’s surrounded by working vineyards.
We also stayed at the 40-room Michelin Key São Lourenço do Barrocal, a sprawling wine estate and olive grove near Monsaraz that has been in the same family for over 200 years. They gave comprehensive wine tastings and vineyard tours, showcasing their centuries-old winemaking traditions.
Our next stop was the Relais & Chateaux property Herdade da Malhadinha Nova, a large farmland estate that required an off-roading experience just to reach check-in. The drive through the countryside was stunning. As a wine lover, I was thrilled to experience their full winery tour, and our dinner there was exceptional. What set this property apart was its incredible range of adventure activities, from horseback riding to ATV tours across the sprawling grounds, plus a world-class spa for relaxation.
Finally, we saw a different side of Alentejo when we traveled to the coastal region of Comporta, popular for its long stretches of white sand beach. We stayed at Sublime Comporta, an upscale resort with luxury villas, private pools, and a 10-minute shuttle to its beach club and coastal restaurant.
We took an 18-mile e-bike ride from São Lourenço do Barrocal to Monsaraz, a well-preserved medieval walled village with narrow cobblestone streets and whitewashed houses. The ride through the countryside was stunning. We rode up a mountain to the Castle of Monsaraz, where we had lunch at Taverna Os Templários overlooking Alqueva Lake with Spain visible in the distance. The e-bikes made it effortless to reach the top, and the views were spectacular.
You're never traveling more than an hour and a half between destinations. The trip is perfect for combining different experiences—you can visit wineries, olive groves, beautiful cities and towns, and then head to the coast for beach time.
This trip is ideal for active travelers and casual wine lovers and enophiles alike. If you enjoy activities like biking, horseback riding, ATV tours, wine tastings and farm-to-table dining, this region of Portugal is a good fit. It's also wonderful for travelers who appreciate luxury accommodations but also want the kind of authentic experiences found in less-crowded destinations. The customizable nature of these trips, with private drivers and guides, makes them suitable for anyone seeking a personalized, upscale adventure in Portugal's stunning countryside.
