You could explore Tuscany for days, weeks and probably months if you wanted. But if you have limited time in the region I have made a selection of the best villages for you to explore to have a true taste of Tuscany.
I organised the list from the further north to the further south, so feel free to scroll through the list if you are only planning to explore one area.
Greve in Chianti
Greve in Chianti is very close to my heart as this is where we used to do our weekly shop with my parents when we were on vacation in Tuscany as a child. We stayed there multiple summers and my favourite thing in Greve in Chianti is to go to the market. The main square gets very busy on market day. Make sure to visit Antica Macelleria Falorni to get some Tuscan products, then grab a table on one of the terraces around the square for a caffe or an Aperol Spritz depending on the time of the day. If you fancy doing a wine tasting Viticcio winery is a very short drive away!
Castellina in Chianti
Castellina in Chianti is a small but lovely medieval village. The perfect spot for a little bit of exploring and watching the local life passing by. I also really recommend having dinner at one of the terraces on the main street. At night, the small quiet village turns into a very lively night life area.
San Gimignano is probably one, if not, the most famous Tuscan village. The medieval town is very famous for its skyline of medieval towers. The place is breathtakingly beautiful. The views onto the Tuscan countryside are dreamy as well. When visiting make sure to take a tour of the Civic Museum and to have the best gelato at Dondoli.
Are you a fan of the Twilight movies? Not really, me neither. Fun fact though, Volterra was the set of one of the movie famous scenes, so if you happen to travel with a fan make sure to mention it to them. You will need good footwear when visiting Volterra as you will be climbing up pretty steep streets, but it absolutely worth it. Walk to the top for some amazing views, take a moment to appreciate the local architecture and on the way down stop for a rewarding gelato or an espresso.
Montepulciano is were the Medieval ages meet the Renaissance. Everywhere you look is a lesson on architecture history. It is a very vibrant little town with plenty of food shops, art galleries and little trendy boutique. A must to add to your Tuscany trip schedule.
I hope this list will help you plan a great trip to Tuscany, as Andrew said the first time I took him there: “Claire, everywhere I look is beautiful!”.
Tuscany never disappoints and it is probably my favourite place in the world. I am so fortunate that it has been my childhood summer vacation destination, and I really hope to carry on that tradition the day I have a family of my own.