The Alentejo is Portugal’s Andalusia, without the crowds. Its much smaller neighbour, the Algarve, gets most of the holiday traffic, leaving the Alentejo’s dozens of beaches all but deserted. Broad sandy swathes backed by caramel-coloured cliffs, rock pool-rich bays and romantic coves. There’s one for every taste.
The Alentejo makes some of Europe’s most underrated wines — rich tangy reds and fruity dry whites. Have a glass or two on the beach, or while sitting in the square of one of the huddles of sugar-cube houses dotted through the region’s rugged interior. Here, you’d be forgiven for thinking there was a fortress on every other crag, and without an apartment block in sight, the views are little changed since Moorish times. Spot lynx and wild boar among the cork oaks and olive groves, and eagles soaring overhead.
The locals are friendly, the food is fresh and fabulous — and it’s always possible to get a table.
What to do
Begin in Evora, the regional capital and one of the oldest settlements in Iberia. Wander round the whitewashed, donkey-wide streets, past crumbling Moorish walls, opulent baroque churches and the romantic ruined shell of a Roman temple. Inside the town museum, Museu Nacional Frei Manuel do Cenaculo, you’ll find Renaissance paintings and sculpture as good as anywhere in Spain (£3; cm-evora.pt).
Kids will love the creepy Chapel of Bones, whose walls are constructed of human skulls and femurs — a legacy of a morbid 16th-century Franciscan abbot, who ordered it to be built as a memento mori to the city’s worldly faithful (£3.50; igrejadesaofrancisco.pt). Grab a picnic — there’s crusty bread, Borba olives and Serpa cheese at the bakeries on Praca do Giraldo square — and drive west to the Almendres Cromlech, a stone circle 3,000 years older than Stonehenge.
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Getting lost in rural Alentejo is a delight. In the Serra de Sao Mamede mountains, near the Spanish border, you’ll find the spectacular medieval village of Marvao. Park at the village gates — set in huge granite walls — and clamber through echoey alleyways to the castle to enjoy views over terracotta roofs and, beyond, forests and lakes.
Nearby is tiny Castelo de Vide, with its bougainvillea-lined backstreets. See if you can find the secret synagogue — hidden in a townhouse and once the heart of a clandestine Jewish community who braved the Inquisition and survived.
Also near the border is Vila Vicosa, which should be visited for the childhood home of Catherine of Braganza, the queen who introduced tea and opera to England. The monumental, marble-fronted Ducal Palace is set in a blinding-white square, with baroque art in the interior (£6; fcbraganca.pt). From here, it’s 16 miles east to the astonishing walled and gated town of Elvas, where a young Wellington began his campaigns against Napoleon in the Peninsular War. The city is crammed with beautiful churches, and a castle, and is ringed with star-shaped forts that are open to visitors.
You can do a wine tour and tasting at the Adega Cartuxa, which is set in the grounds of a 16th-century Carthusian monastery near Evora. My pick? The big-bodied, oak-cask matured Tinto Reserva 2013 (tours from £4; cartuxa.pt). Or try the prize-winning reds at Reynolds, whose 17th-century barns house state-of-the art wine-making equipment. It was founded by a descendant of the painter Sir Joshua Reynolds, and is still run by the family (by appointment; reynoldswinegrowers.com).
The beaches
Troia, just south of Lisbon, is the only real resort town, but with just a handful of hotels set on a small harbour, it still feels barely larger than a village. It sits at the tip of a 10-mile-long sandy spit, with a birdlife-rich estuary on one side and miles of perfect sand dunes on the other. If you can’t find your very own stretch here, you’re just not trying.
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A couple of hours’ drive south is Vila Nova de Milfontes, a fishing village surrounded by sheltered bays and broad strands of golden sand. There’s great walking further south still, on the Costa Vicentina coastal trail, which cuts through meadows and rounds capes all the way to the Algarve. Look out for nesting storks and harriers (en.rotavicentina.com).
Where to eat
Pull up a chair in the bright, modish dining room at Tasca do Celso, in Milfontes, and order rice with razor clams and tiger prawns, or baby squid cooked in olive oil and whole garlic cloves. You won’t regret it — certainly not at these prices (dishes from £8; tascadocelso.com).
The central Alentejo is renowned for its acorn-fed black pigs. Enjoy pork served traditionally a Alentejana (with juicy black olives and clams) at ¼ Pras 9 (mains from £12; restaurante14pras9.pt), or with a modern twist and migas bread sauce in the candlelit vaults of a restored convent at Divinus (mains from £22; divinusrestaurante.com). Both are in Evora.
The hilly northern Alentejo is known for its game and wild mushrooms. At the Feitico da Moura, which is set in a converted estancia outside the hilltop village of Monsaraz, they are cooked by the prize-winning chef Henrique Mouro and come with a sweeping view of the plains (mains from £20; hortadamoura.pt).
Where to stay
Pousadas are Portugal’s equivalent of Spanish paradors — luxury hotels in historic buildings. The most impressive are the Convento Evora (doubles from £115, B&B; pousadas.pt), Espinheiro (doubles from £121, B&B; conventodoespinheiro.com) and Sao Paulo (doubles from £65, B&B; hotelconventosaopaulo.com). All three are housed in magnificent cloistered convents in and around Evora, with rococo chapels and period furnishings.
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There are a handful of resorts, from romantic and boutiquey to family-friendly. L’And, near Montemor-o-Novo, is a fashionably minimalist spa and winery. Rooms sit in brilliant-white concrete wedges fronted with glass and set in an olive grove. Michelin-starred dishes by Miguel Laffan (with wines from the hotel vineyard) include roast merino lamb with yoghurt and fresh mint (doubles from £135, B&B; l-and.com). On the Estuario do Sado nature reserve, the Herdade do Montalvo has an array of modern beachside villas with lawned gardens, pools and tennis courts (villas from £105 a night; herdademontalvo.com).
Pensoes or residencias are simple B&Bs, often family-run. Dona Idalia is an energetic grandmother who lives on the premises at Casa do Adro in Milfontes, and serves afternoon tea and home-baked cake. The rooms are small but cosy, with balconies overlooking the church. The beach is a five-minute walk (doubles from £65, B&B; casadoadro.com.pt).
Getting there
Fly to Lisbon or Faro — which are both within an hour’s drive of the Alentejo — with British Airways or easyJet. Sunvil has 10-day trips to the Alentejo from £1,043pp, B&B, including flights (sunvil.co.uk).