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.
My recommended list of vacation rentals in Chianti.
A list of great places to stay in Tuscany.
Some specific properties that I recommend.
Useful information for visitors to the Chianti area.
Main sights of the Val d’Orcia.
About Elena Spolaor
Although Elena was born in Venice, she was brought up in Tuscany and is a historian and frequent contributor to online articles about life in Tuscany and Umbria. Her specialities are Tuscan and Umbrian local history and folklore.
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Hi Elena, my boyfriend and I are trying to decide between Castellina and Greve in Chianti as a base for our vacation in Tuscany. Both areas seem to offer a lot. Can you provide any tips in terms of pros and cons?
Hello Rose, your decision will very likely depend on whether or not you will have a car and the relative priorities you give to visiting Siena and Florence. There are nice agriturismi near both Castellina and Chianti, plus reasonable restaurants, although Greve has more of both. HOWEVER, if you are travelling by bus, you can go to and fro between Greve and Florence easily, and between Castellina and Siena easily, but not vice versa. To go by bus from Greve to Siena you have to travel one hour into Florence and take the SITA express bus (same bus station) to Siena. This can be done, of course, but it limits your day length because the last bus from Florence to Greve is at about 8 pm. If you will have a car, this issue disappears.