Some of the best custom days begin in the part of Tuscany I know best: Montepulciano, Pienza and the Val d’Orcia countryside.
These places are close enough to work naturally together while offering very different experiences — Renaissance hill towns, vineyards, family wineries, Pecorino cheese, cypress-lined landscapes and small countryside roads.
A private Val d’Orcia tour might include a morning in Pienza, a scenic countryside drive, lunch at a family-run farm or winery and an afternoon wine tasting near Montepulciano.
Another day might skip the towns almost entirely and focus on food, wine and countryside.
That’s the advantage of a custom itinerary: we build around what interests you instead of forcing every guest through the same route.