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 most beautiful villages for you to explore to have a true taste of Tuscany.
I organised the list from the further north village to the further south one, 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 cafe 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 nightlife area.
San Gimignano
San Gimignano is probably one of, 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.
Volterra
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
Montepulciano is where 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 do to add to your Tuscany trip schedule.
Of course, also make sure to spend some time in Tuscany’s main cities: Florence, Siena and Pisa. 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, with its excellent food, stunning landscape and beautiful villages it is probably one of my favourite places 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.
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Claire Imaginarium 
I wish I could go back to Tuscany and explore these places! Have you been to Siena?
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Yes! About 5 times! It is my favourite city there!
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They are lovely. I love older charming authentic villages like that. You really learn about the coutries culture from them.
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I have been reading a lot of posts on Tuscany of late. But this one has to stand out for sure. I loved all the villages mentioned by you but Volterra has to stand out for sure!
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I LOVE Tuscany!! Got to spend some time there earlier this year. I didn’t get to all of these, but I did visit some that aren’t on your list, like Siena and Montalcino and Barga. Barga was especially beautiful being up in the mountains!
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I’ve heard of Tuscany but I never knew it is so beautiful. All these places you’ve listed look amazing and it’s hard to choose which one I would love to visit most. I would so love to explore all of them. And I complete agree wherever you see, it’s all beautiful. Hopefully, I’ll get a chance to visit Tuscany some day and explore it’s hidden treasures. Thanks for sharing. 🙂
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Tuscany is just so lovely! You’ll love it!
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Your post is such a treasure for a countryside lover like me. I always prefer villages over cities. Thanks much for this lovely list of villages. Shall plan soon.
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Thanks!!!
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It makes me so happy that San Gimignano is on this list! I had the BEST gelato of my life there lol
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Yes!!! Chances are this is where you went https://claireimaginarium.com/2017/09/03/best-gelato-in-tuscany/
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This place looks so beautiful, like a medieval movie setting. Definitely worth adding in travel bucket list.
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This brings back lovely memories! We’ve been to a few of these beautiful little villages last year and now have some more to look forward to visiting! Lovely pics, they bring Tuscany to life.
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Thanks!
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Wow! These are breathtaking and beautiful. While its very hard to say one is better than the other, Volterra stands out. Would love to climb all the way up for the views!
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Quite an interesting mix of places. I have two weeks off in January and am thinking where to travel to. Is there anywhere in Tuscany that you would recommend that is not too cold in January?
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Great post! We haven’t been to Tuscany yet but would definitely pick Greve in Chianti! It sounds like our type of place with the markets and we do love Chianti wine as well, not so much Aperol though, I think it is an acquired taste.
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I have wanted to go to Tuscany ever since I saw the movie “Under The Tuscan Sun”. However, I had no idea where to go and what to do. Your post is great. Now, I know where to start. Thanks!
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Italy has been one of my favorite country. Its art, architecture, heritage, landscape and the cuisine, all I love. I have visited Tuscany region too. Love your depiction of Tuscany villages.
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I have always wanted to explore all the cities in Italy and am actually going to Rome next weekend! Having read this, I’m going to put Tuscany on my list too!
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Names that have fed my dreams of Italy for many years and I simply can’t wait to do every single one of the list. Your photos are lovely and convince me I chose the right villages to visit.
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This post has given me serious wanderlust! I love the look of these villages and you’ve captured them perfectly!
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I’ve only every been to Sicily in Italy, but now you made me want to explore all of Italy 🙂 I love to explore to small villages in big countries and I think Tuscany will be my first stop in Italy 🙂
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Beautiful post Claire. I have plans to go to Tuscany next year, thanks for adding to my inspiration 😀
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I love Italy there are so many beautiful places to see, loved the photography in you post. Tuscany is wonderful I had a fantastic time when I visited. Will deffo have to go back again.
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This is a fantastic list! I have always wanted to visit Tuscany. I didn’t realise that Volterra was the set for the Twilight movie. The villages are perfect to explore, grab a bite to eat and watch the world go by. This is on my list!
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I am actually going to Tuscany for a month and I am looking forward to explore all the little villages (and wineries). I will be staying in a village myself and I have already rented a motorbike for the entire trip. I am so looking forward to explore the entire county. I will definitely go to San Gimignano and to Volterra.
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Although I haven’t been to Tuscany myself I do know of its Beauty and charm, I used to sell holidays for Tuscany and everybody I sent over there always had only positives to say about it. Do you think it’d becoming over-touristy or still ok ?
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It’s still okay if you avoid July and August when all Europeans are on vacations 🙂
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I’v always dreamt of walking by the quiet alleys of Tuscany. If I had to pick my favourites, I’d choose San Gimignano and Volterra. Cheers!!
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How lucky you were to spend family holidays here. Great tip on the medieval village. Tuscany seems very tranquil and beautiful. thanks for sharing
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That reminds me of the movie UNDER THE SUN OF TUSCANY have you watched it? It makes you wanna go immediately!! I can imagine all the villages are pretty amazing there (your pictures only confirm!) and the food mmm.. sounds like the perfect holiday destination! Did you rent a car or did you travel by public transport?
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I have seen the film and realty is very similar 🙂 Yes always renting a car there so we can do everything freely!
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Great post! Tuscany is one of a kind. The information on the different villages is so informative and definitely helpful!
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I’ve been torn between going to Tuscany or another area on our next trip but I think these villages may have made the decision for me! Thank you.
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Tuscan villages are really beautiful! I like the ambience and the easy going way of life. While living in a bustling metropolis like Delhi, you miss the charm of a laid back environment. Montepulciano is a must visit thanks to your blog.
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Love this post – I can’t wait to get to visit Italy again!
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Great visit you have done, I remember my days in italy too. and Yes I am a twilight fan your soooo Lucky to be there in Volterra I’m sure it’s a nice place. love you post.
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I’ve never been to Italy but it seems amazing! I love medieval villages, the architecture and history. Your pictures and memories of each place is brilliant!
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We were so lucky to visit these villages this year, I would add just one more Lucignano (but don’t tell anyone else)😉
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This is exactly like I imagined it would be! Such a gorgeous italy city…forever on my bucket list. Maybe someday Ill get the money for it…
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I have explored lot of parts of Italy but not been yet to Tuscan region. Quite excited now.
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There really is nowhere on earth quite like Italy is there. I love that this post is focused on villages, they’re my favourite part of Italy! I’ve been to loads in Veneto… maybe it’s time I moved over to the other side of the country and checked out some of these!
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Been a while when I was in Tuscany… Pisa, Florence, Livorno and the Grotta del Vento… I really should have rented a car back then to visit some of the small villages… Have to return there one day – especially after reading your post 🙂
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Tuscan is always a nice choice! Still on my bucket list but I will definitely visit all beautiful places around.
Thanks for the post and good luck 🙂
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Italy is always a good Idea! Too bad you sometimes have to rent a car to explore the whole country. I love all the small villages
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