This area offers a rural landscape unlike anywhere else in Portugal, with rolling grass plains and undulating corn fields interspersed with sprawling forests of cork oaks and pine. Down along the coast, the long, sandy beaches are brisker and breezier than the Algarve, and crowd-free. The pace of life here is southern and slow, so linger in the little villages that appear like tiny nests of whitewashed houses, while enjoying local wines and scoffing traditional sweets from local monasteries.
Take time to explore the hills, which conceal regal Roman temples at Evora, and crumbling medieval ruins at Monsaraz. Dine underneath 18th-century frescoes at the Hotel Convento de São Paulo, a beautiful 12th-century convent converted into a comfortable hotel.
Stay: The quiet and peaceful Hotel Convento de São Paulo, which is a converted convent.
Rooms from Dhs450-Dhs1,200. www.hotelconventospaulo.com (+351 266 989 160).