Tuscany

Order the hand-cut pici in a stone-vaulted cantina in Montalcino. Watch the Val d’Orcia light go rose-gold at dusk over the lone cypress ridgelines. Arrive at your 13th-century farmhouse conversion with vines pressed up against the shuttered windows. Tuscany is Italy at its most densely rewarding, and it has been that way long enough to know exactly what it is doing.

The range of accommodation here is serious. Converted convents and former monastery hotels now run candlelit restaurants and infinity pools above the hills. Entire fortified borghi have been turned into private estate hotels where you may be one of a handful of guests. Wine estates in Chianti and Montalcino put you among the vines, with the winemaker available for private tastings during harvest. Even an agriturismo, a working farm stay, will put locally pressed olive oil, estate wine, and cured meats on the breakfast table without making a fuss about it.

The Val d’Orcia south of Siena is the visual anchor of the region: rolling hills, those lone cypress ridgelines, medieval towns rising above fog-filled valleys. It is a UNESCO World Heritage landscape and it earns it. Pienza, Montalcino, and Montepulciano form a tight triangle of serious food, wine, and architecture all within easy driving distance. Pienza was redesigned in the 15th century as a model Renaissance city by Pope Pius II and is still essentially unchanged. The pecorino cheese alone is worth stopping for.

The wine geography rewards proper attention. Chianti Classico, Brunello di Montalcino, Vino Nobile di Montepulciano, and Morellino di Scansano each have distinct terroir and character that no label fully communicates. The Strada del Vino through Chianti runs between Florence and Siena through ancient estates, olive groves, and family cellars where tasting with the producer directly is still how things work.

Florence is an exceptional city packed into a walkable historic center. The Uffizi alone holds more Renaissance masterworks than most countries’ entire collections. But Siena, Lucca, Arezzo, and Cortona offer comparable medieval grandeur with a fraction of the crowds. The accommodation in those smaller cities tends to be better value and considerably more interesting.