Portugal Private Journey

Hiking the Hidden Towns of Alentejo

With walled hilltop villages crowned by ancient castles, whitewashed houses gleaming in the sun, extraordinary megalithic monuments including stone circles, and the legacies of the Romans and Moors, the Alentejo is a captivating part of Portugal—and still relatively undiscovered. On this Private Journey, you’ll walk historic paths from one village to the next, soak up the atmospheric past as you explore Roman monuments and the evocative remains of Moorish castles, and visit award-winning wineries and even a gin distillery (with tastings, of course!). Many of the hikes begin or end right at your hotel, and they are flexible in length (your choice). Most of the accommodations are in lovely pousadas, traditional or historic properties that help tell the story of Portugal’s past. Throughout the journey, you’ll sample the traditional local dishes of Alentejo, one of the most distinctive regional cuisines in all Portugal.

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