Tuscany, 6–7 days, self-drive
Florence earns two days, not the whole trip — the region’s real character is in its hill towns. San Gimignano’s medieval stone towers, Montepulciano’s wine cellars carved into the hillside, and Pienza’s Renaissance-planned streets (built as an ideal city in the 1460s) each feel genuinely distinct despite sitting less than an hour apart.
Base in the Val d’Orcia countryside rather than a single town — it puts multiple hill towns within a short drive and delivers the classic cypress-lined-road Tuscan landscape as your daily view rather than a single day-trip photo stop.
Visit at least one working vineyard for a tasting that includes the cellar and vines, not just a tasting-room pour — Montalcino’s Brunello producers are used to genuine visits, not just tour-bus stops.
Typical range: €130–€350 per night for agriturismo and countryside stays.
Sephari’s Curated Travel Outfits collection has the layers suited to Tuscany’s warm days and notably cooler countryside evenings.