If we were being honest, before our first visit to Portugal, we had never heard of Alentejo or its delicious wines. One trip to Évora, the hub of eastern Alentejo, and we were hooked. We’ve since returned many times and the region has become one of our favorites in Portugal.

The Alentejo region stretches from the Spanish border in the east to the Atlantic Ocean in the west like the kneecaps to the waistband of Portugal. Amidst olive groves, vineyards and farmland in the east, you’ll find red-roofed, whitewashed hilltop towns overlooking the plains like feudal lords. As you travel westward towards the beautiful windswept beaches of Comporta along the back roads amidst cork groves (link tribute to some bloggers we follow: Salt of Portugal), you’ll be observed by storks nesting atop buildings, power line towers and trees in nests large enough to share with many undelivered newborn babies.

Interior Alentejo

Évora is one of our favorite small cities in Portugal. Surrounded by miles of vineyards, farmland and pastures you roll into town past evidence of the Roman trade routes and within the area you can visit megaliths which provide evidence of humanity pre-Romans. Évora is now a college town (and has been for a long time). Good restaurants, beautiful winding streets, an aqueduct stretching through town and a former Temple to Diana are some of the sights to see. For a morbid history lesson on mortality, visit the Capela dos Ossos (the “bone church”). Évora is good hub for exploring eastern Alentejo.

The Wine Hotels. Throughout Portugal, there are several “wine hotels” which are hotels with activities (horseback riding, hot air ballooning, wildlife viewing safaris, etc.) in the midst of expansive active farms and vineyards. We’ve stayed in some of these up north and here is a list of those we’ve visited and stayed at in Alentejo (yes, right now the list is short so we’ve got a lot of work to do. We won’t list any here we don’t strongly recommend):

Herdade do Sobroso, Pedrogao. Sobroso is definitely off the beaten path. We loved it. We did the photo safari, strolled the grounds and did the wine tasting. Ótimo!

Elvas. On the far eastern border of Alentejo sits the military base and town of Elvas. We stopped off in Elvas for an overnight and will definitely return. Its thick walls surrounding town require blowing your horn as you drive through them, to warn oncoming traffic of your arrival. A massive aqueduct sits just outside of town. We loved our experiences in Elvas: dinner, overnight and a visit to the Military Museum. Worth a stop off if you’re in the area.

Monsaraz. The magical, hilltop community of Monsaraz overlooks the largest freshwater lake in Portugal (Aqueva Lake) and is in the heart of certified dark sky country. There’s an observatory just outside of town where you can star gaze and the town itself is an artist community with small shops, a few restaurants and a couple of hotels. We chose to spend New Year’s Eve here at the end of 2019 and it was one of our favorite experiences in Portugal. You can read about our whole winter 2019-2020 trip here.

Coastal Alentejo

Comporta Area. The Comporta peninsula is gaining popularity and is beautiful. Salt marshes, estuaries, sparklingly bright flat beaches, resort hotels, sea sports, great restaurants and storks overlooking it all from rooftop and powerline roosts. What’s not to love? We visited Comporta in the offseason as it is extremely pricey during the summer and will definitely return, especially when a deal can be found.

We will continue to update this page as we continue to explore this beloved region, so check back periodically.