Apr.6.2021
There are many good road trips out there, but driving through Tuscany is on a whole other level. Tuscany is a very manageable region, size-wise, roughly the size of New Jersey, and has a good and easy to maneuver road system. The countryside is picture-book perfect, with green hills dotted with slender cypress trees standing in line, vineyards, and sunflower fields at every corner, and pretty much every single town and village worth stopping off at.
It is gorgeous in summer, but it gets extremely hot in the narrow medieval town centers -- too hot to sightsee, really. In spring you can get a fair bit of rain, explaining the lush green countryside, but early fall is quite perfect. If you can aim for early or mid-September, then you get the best of everything.