Monsaraz is surely the place to let you breathe in the truly medieval Portugal. Sitting above the River Guardiana on the frontier with Spain, the tiny Middle Age walled town is one of the most atmospheric places in the region of Alentejo. The massive castle keeps a wary eye on the Spaniards in the distance and the cobbled narrow lanes and low-rise old houses dotted with ambient hideaways guarantee a laidback afternoon over a glass of wine or local dishes. Amble along the nearly deserted streets at a leisurely pace taking in the atmosphere of this amazingly well-preserved part of Portuguese history. Don't miss the castle or the parish church of Santa Maria and for some shopping make for the village of São Pedro do Corval famed for its pots and other locally produced ceramics.