From Siena’s magnificent squares to the “medieval skyscrapers” of San Gimignano, via rolling hills striped with vines. Tips for one of Tuscany’s best-loved itineraries.

SIENA

Known all over the world for its historical Palio horse race, Siena is a treasure trove of unparalleled beauty, and still protected by its ancient city walls. It all revolves around Piazza del Campo, the beating heart of the city and home to Palazzo Pubblico and the Mangia Tower which – if the more than 300 stairs don’t put you off – offers one of the most delightful views of Siena. Of course, you shouldn’t miss the Cathedral, which at certain times of year uncovers its extraordinary marble floor panels, revealing a unique masterpiece in all its splendour. It’s also impossible to visit Siena without enjoying a delicious plate of pici al ragù accompanied by a glass of Chianti Colli Senesi DOCG, perhaps at Taverna di San Giuseppe or Compagnia dei Vinattieri. And if you choose to stay longer in the city, there’s the Grand Hotel Continental, 5 stars of pure magic.

SAN GIMIGNANO

Just over half an hour’s drive through Siena’s gentle hills takes you to San Gimignano, where you’ll immediately realise why the town is nicknamed the medieval Manhattan. Unmissable sights are the Cathedral – the contrast between the bare exterior and the extraordinary frescoed interior will take your breath away! – and the stunning Piazza della Cisterna, where you can enjoy an excellent ice cream at the multi-award-winning Gelateria Dondoli. Lose yourself among the narrow  streets and marvel at the 13 towers remaining of the original 72. If you fancy a platter of cured meats including wild boar, along with fresh pecorino and local honey and accompanied by a great glass of Vernaccia, don’t forget to stop at La Vecchia Nicchia. For a special dinner in a warm, inviting setting, we recommend La Mandragola; you won’t be disappointed.