One of my strongest recommendations for getting the most out of your vacation in Tuscany is to choose a single base and explore Tuscany from there. Why do I say that? I find that many visitors to Tuscany greatly underestimate the amount of time that will be lost each time they change accommodation. That includes finding the place, finding parking, checking in, unpacking, and then the same in reverse. It’s both more efficient and more relaxing to find a good place to stay, settle in and explore from there. Tuscany is not very big and although the country roads mean slower speeds than on an autostrada, choosing a central location means that you can do day trips to almost every sight of interest in Tuscany.
So where is the best place to stay as a base to explore Tuscany? Long experience suggests two areas. The first is Chianti, the area between Florence and Sienna. The second is the Val d’Orcia, south of Sienna. Personally, I prefer Chianti because it is within very easy reach of both Florence and Sienna, and is not only full of interest in terms of villages, abbeys and castles but also very well-endowed with country vacation accommodation. The Val d’Orcia is less central but puts parts of Umbria within easy reach. The Val d’Orcia is, of course, famous for is spectacular, wide-open landscapes. and is the location of some beautiful italianate gardens, notably at Villa Le Foce and the Palazzo Piccolomini in Pienza.