With Lisbon arriving at-capacity and the stylish outpost Comporta a secret no more, the largely unsung Alentejo region is gaining status for travelers in southern Portugal. The country’s biggest region, it is buffeted from the mega-tourism of the Algarve coast to the south and distinguished by a pastoral charm with whitewashed villages giving way to cork-oak forests, wheat fields, wildflower meadows and vineyards yielding rich and robust reds and delicately balanced whites.

Some of its most memorable lodging is found among the historic pousadas dotted throughout the region. A network of formerly state-run hotels folded into castles, convents and palaces, the design of the more traditional of these properties often embodies a certain monastic restraint favoring simplicity over baroque pomp.

A growing choice of more modern accommodations are emerging, too, such as São Lourenço do Barrocal, a country estate near the Spanish border. Set within a working vineyard and olive grove, it offers chicly decorated suites, cottages and rooms converted from barns and farmers’ quarters by one of Portugal’s foremost architects, Souto de Moura. The on-site restaurant serves wines produced at the estate alongside local produce and porco preto (black pork) from acorn-eating Iberian pigs.

Nearby lies Monsaraz, a hilltop village with cobbled lanes and a medieval city wall, here local artisans carry forward one of the region’s many craft practices, hand-weaving traditional rugs in vibrant colors.

Tracking west to the coast, Alentejo’s bucolic calm ends abruptly at the Atlantic Ocean, where there is drama in spades. The beautifully rugged coastline is largely protected by national-park status, safeguarding some of Europe’s best-preserved beaches.

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