Castles and convents dominate Portugal’s Alentejan landscape, but, to truly understand the region’s rich history, you’re best just looking at your plate: Roman rule, Moorish invasions and Christian conquests have all left their mark. Stay at Herdade da Malhadinha Nova , a 17th-century wine-producing estate where Michelin-starred chef Joachim Koerper adds his own twist to traditional Alentejan recipes with dishes such as oxtail with the smoothest sweet potato purée and a perfectly poached egg (€20).
Travel 20km northeast to Beja, where elderly men in berets watch the world go by while women keep centuries-old baking traditions alive. In the 16th century, the question on every royal’s sugar-coated lips was, ‘which convent makes the best cakes?’ The city’s green pumpkin, cinnamon, honey and almond pastries remain as enticing today. Find them at Casa de Chá Maltesinhas (Terreiro dos Valentes, 00 351 284 321 500), around €1 each.
Stop for lunch at Villa das Frades, site of the São Cucufate Roman ruins. Here, the País das Uvas bodega (Rua General Humberto Delgado 19, 00 351 284 441 023) makes wine the Roman way – in clay vats. Try the fruity white with Alentejo’s most famous export, acorn-fed grilled black pig, porco preto, (€11.50) served grilled with garlicky wild asparagus (€7.50).
Next morning, stroll through the hilltop town of Monsaraz before lunching on açorda (€7.50), a fish broth with made with bread, garlic and coriander, at nearby Horta da Moura (hortadamoura.pt). Last stop is Évora’s Convento do Espinheiro, a 15th century converted convent where you can feast on Alentejan tapas (€45.50) in the monks’ former cellar before sinking into bed in rooms once occupied by Portuguese kings.
HOW TO DO IT: Alentejo food and wine tours cost from £689 per person, including four nights’ B&B accommodation, car hire and flights (sunvil.co.uk).