A Perfect Day in Alentejo: Medieval Villages & Roman Ruins

Some days on our trips are designed to surprise you with just how much history exists in one region—and Day 7 of our Coastlines & Castles journey does exactly that.

We'll wake at Convento do Espinheiro, a 15th-century convent turned luxury hotel set on acres of gardens—the perfect peaceful base for exploring this historic region.

After breakfast, we'll head to Arraiolos, a medieval hilltop village crowned by one of the world's few circular castles. This is Portugal's tapestry capital, where artisans still practice the same techniques they've used for centuries. Walking these cobblestone streets feels like stepping back to the 1500s—in the best possible way.

Then we're off to Évora, a UNESCO World Heritage city where 2,000 years of history unfold around every corner. Our expert local guide will take us through Portugal's largest medieval cathedral, past perfectly preserved Roman ruins, and into the remarkable Capela dos Ossos—a chapel whose walls are lined with thousands of bones, created by Franciscan monks as a meditation on mortality. It's haunting, beautiful, and completely unforgettable.

Lunch is at your own pace (we'll point you toward our favorite spots), then we'll return to the peaceful sanctuary of Convento do Espinheiro. Dinner at the acclaimed Divinus restaurant—right in the hotel's historic vaulted dining room—caps off a day steeped in Portuguese history.

This is the kind of day that reminds you why we travel—to connect with places where history isn't just preserved, it's still lived.

Ready to see all 11 days? Check out the complete itinerary on our website.