Pousada Mosteiro Crato

A former castle, ducal palace, monastery, and convent, this pousada in the Alentejo countryside has had more past lives than most small towns. Rooms are sleek and modern against all that ancient stonework, the pool sits in the shadow of the old façade, and the restaurant leans into the region's reputation for excellent cheese, olive oil, and slow-braised everything. The Alentejo is sometimes called Portugal's Tuscany, back when Tuscany was still a secret.