It is well known to oenologists, but a little surprising to the rest of us, that the region is not only by far Portugal’s prime producer of plonk, but increasingly the source of some genuinely classy and sophisticated wines. The headquarters of the local wine authority, Vinhos do Alentejo, on Praca Aguiar, is a good first port of call for a bit of background on race local grape varieties such as Alicante Bouschet, Antão Vaz and Roupeiro. Thereafter, armed with the Wine Route map, you could take to the road, as I did, for a vinous safari taking in producers such as Cartuxa – on a historic estate run as a philanthropic enterprise by the Eugénio de Almeida Foundation – Quinta do Carmo and Monte dos Coelheiros. You could stop for a long lunch in a wine village such as Reguengos or Borba, then make for Monsaraz to watch the sun go down over the reservoir before heading back to your hotel.

Description: Praca Aguiar

Vamos passar pela praça medieval

But which hotel? For the moment there are two five-star properties in Evora, and the only important decision you will need to make in this least stressful of cities will be which of the two to book into. Classic luxury or contemporary chic?

The brand-new M’Ar De Ar Aqueduto hotel, fashioned out of a palatial house beside a 16th-century aqueduct, lies inside the city walls and is to be recommended for its swish modern design and perfectly convenient setting.

Description: the Virgin Mary church

the Virgin Mary church

The Convento do Espinheiro is clearly the posher option. Part of the Starwood hotel group’s Luxury Collection portfolio, it is a converted convent originally built in the 15th century after the Virgin Mary was said to have appeared to a shepherd in a hawthorn tree (espinheiro). The hotel stands in rolling countryside a few kilometers outside Evora, and the whitewashed splendor of the convent church is visible from the town.

The convent’s plain, cool interiors with impressive vaulted ceilings have been skifully turned into five-star spaces by the judicious application of expensive fabrics, ecclesiastical accoutrements and comfortable (if not always especially beautiful) furniture. The music in the hotel’s public spaces reflects the odd convergence going on here: there is Chopin in the refectory lounge, Pet Shop Boys in the breakfast room and plainsong in the convent church.

At least the church – a sizeable Renaissance structure with a rich gold altarpiece, an organ, side chapels and a series of wonderful painted blue azulejos illustrating scenes from the life of St Jerome – is still functioning as such. After a long dinner with a bottle of strong local red wine. I enjoyed the sacrilegious frisson of emerging directly from the restaurant into the deserted church for a moment a post-prandial meditation.

My room at the Convento do Espinheiro was anything but monastic, with a rococo bed, hardwood armchairs, heavy curtains and a palette of purple, red and grey. Above the bed, a picture of the Good Shepherd holding a sheep looked down on me beadily (and, so I fancied, slightly reprovingly). The view from the balcony was pleasant but slightly disappointing: a jumble of semi-rural plots beyond the pool.

After two nights I asked to change rooms, and the new one was more to my liking: a sleekly modern suite in the hotel’s newest wing – built in 2008 – with furniture by Dolce & Gabbana and Philippe Starck, a sunken hydro-massage tub in the white marble bathroom, and a salacious modern painting by the Portuguese painter Bela Silva – a considerable improvement, I thought, on the Good Shepherd. Outside the balcony were rocks and pasture, and the white pavilion of a mausoleum deep in the convent grounds, reminding me of the grave of some Islamic saint.

Description: the Praca do Giraldo

the Praca do Giraldo

Since it was my last night, I drove back into Evora for a walk around the old town under an enormous full moon, so bright and close it seemed to flood the whitewash of the town with ultraviolet light. On a week night the Praca do Giraldo was deserted, and I sat by the fountain in contented solitude, admiring what is surely one of the world’s most peaceful urban spaces. Like many a wised-up beauty. Evora likes to turn in early, the better to show off her fresh-faced loveliness the following day.

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