
Villa Sassolini
Tuscany, Italy
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Chianti, at the heart of Tuscany, encompasses immensely charming abbey-, winery- and castle-capped cities. See Siena’s striped churches; Florence’s museums, Medici tombs and Madonnas; Greve’s mediaeval relics; and enough vineyards to keep your glasses topped up and toast-ready. Wine takes precedence here, with a strict Chianti Classico production zone and eight subzones for variations on the titular tipple. Take note: the typical straw fiascos are mostly rustic set-dressing nowadays. Emigrés and celebrities have snapped up Chianti’s crumbling homesteads, earning it the nickname ‘Chiantishire’; but the stomping ground of Machiavelli, Leonardo and Galileo has an incorruptible charm, and remains one of the world’s most enchanting destinations.
In summer Chianti throngs with tourists and fair-weather villa owners; it’s best to visit in September or October when temperatures are milder. Visit the Chianti Classico wine festival in early September, when regional producers bring a mind-boggling variety of top vintages to Greve.