Tuscany

Tuscany is the Italian region that ruined every other landscape for you. The hills roll in exactly the way you expect from every olive oil label and wine bottle you have ever seen, except in person the colours are better and the food is cheaper. Florence anchors the north with 500 years of art stacked in galleries that could occupy you for a month. Siena owns the middle ages - the shell-shaped piazza, the contrade rivalries, the Palio. San Gimignano kept its medieval towers when every other town tore theirs down. And the Val d'Orcia in the south is UNESCO-listed because even bureaucrats occasionally recognise beauty when it is this obvious. The wine and food alone justify the trip. Chianti Classico from vineyards between Florence and Siena (EUR 8-15/bottle at the cellar door), Brunello di Montalcino from the southern hill town that produces one of Italy's greatest reds (EUR 30-80/bottle), Vino Nobile di Montepulciano from underground cellars carved into Etruscan caves (EUR 10-25), and Vernaccia di San Gimignano (the white, EUR 8-15). The food matches: bistecca alla fiorentina (the massive T-bone steak, 1 kg minimum, rare, shared), pici with wild boar ragu in Siena, pecorino in Pienza where the cheese shops offer free tastings that could constitute lunch, and ribollita (the bread soup) everywhere. The driving is the connective tissue. The cypress-lined roads between towns, the SR222 Chiantigiana route through wine country, the approach to hilltop towns that appear and disappear as the road curves - these are not transfers between destinations, they are the destination. Rent a small car, bring good sunglasses, and accept that you will stop for photographs more often than the itinerary suggests.