Driving the famous wine region Chianti in Tuscany Italy

The Chianti Classico is a famous wine growing region in Tuscany Italy.

Located between Florence and Siena, Chianti is characterized by it’s medieval towns and picturesque rolling hills covered in forests, vineyards and olive groves, making it one of the most beautiful regions in Italy.

view of a vineyard in Chianti, Italy

Tuscany, Italy

On a fresh Autumn morning, my wife and I awoke in our rented Tuscan villa to see amazing blue skies outside our window, the sun lighting up the vineyard across from our terrace. After enjoying a delicious alfresco breakfast, we decided to set off for the day to explore the area.

Although driving in Italy can at times be quite hair raising, I found driving through the Tuscan countryside to be relaxing. The roads twist and turn up hills and down through valleys, passing peaceful forests and small farms with their centuries old farm houses, all with their own vineyards, olive groves and vegetable gardens.

After going through several small villages, we headed towards the larger town of Greve in Chianti to stop and explore.

Greve in Chianti, Italy

Exploring Chianti

Walking down the narrow cobble stoned streets, we made our way to the main town square. The village seems to have remained as it has always been, it’s main piazza surrounded by tiny shops and cafes, with it’s beautiful church dominating one end.

We walked around the piazza checking out local handicrafts, sampling meats and cheeses and sitting down to enjoy a cappuccino. Of course we couldn’t forget about what Chianti is famous for, it’s amazing wine. And there is plenty of it to taste and purchase.

An old classic truck in Greve in Chianti, Italy
An old classic truck in Greve in Chianti, Italy

We spent the early afternoon exploring the little streets and climbing up a steep path to get a nice view out across the town, before driving back to our villa.

road trip Chianti Italy Tuscany

Chianti Classico

A couple of days later we got to take another drive through the beautiful Chianti Classico on our way to Siena, this time taking us past Greve to another main town in the region, Castellina in Chianti.

Since we were passing by I just had to stop and spend some of our morning exploring the village. Castellina in Chianti is dominated by it’s amazing 15th century fortress in the center of town.

A fortress in Castellina in Chianti
A fortress in Castellina in Chianti

Winding our way through the tiny cobble stoned streets, we stopped at a cafe for a cappuccino and passed by Castellina’s old 16th Century church. It seemed as though everyone hadn’t even woken up yet as we explored the town, apart from the cafe nothing else seemed to be open yet and very few locals were out and about.

From first impressions it seems like a cozy, sleepy little town with a lot of character and history.

Church in Castellina in Chianti, Italy

We walked through a tunnel that runs through one of the old medieval walls that surrounded the town, before continuing our drive through the Chianti countryside to Siena.

On our way back from Siena in the warmth of the late afternoon, I took a different route through Radda in Chianti, another beautiful looking village. Driving through the forested hills on the way back to our villa, a deer leaped across the road and continued it’s way up the slope. This place just has beauty written all over it.

Having a villa to base ourselves whilst in Tuscany, meant that we could truly experience this area. Shopping for local produce, we got to meet the local people and share this amazing place that they call home.

The lifestyle here is so relaxed and peaceful that I think the Chianti region is a place that I could live for a while.

If you’re going to Tuscany, I highly recommend hiring a car and exploring the countryside. Chianti is truly a beautiful place.

Plan Your Trip to Tuscany, Italy

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More posts about Italy:

Dean is an intrepid traveller from Australia. He travels whenever and where ever he can to explore new places, experience new cultures and taste new food. He hopes to inspire other people to travel through his articles and photos on his travel blog, The Road to Anywhere. You can connect with him on Facebook and Twitter.

Have you been to Tuscany before? Share your experiences in the comments below.

20 thoughts on “Driving the famous wine region Chianti in Tuscany Italy”

  1. I always ask for excuse for my bad english (Google style). I could not remain silent,I’m Italian and I’m happy when it comes to my beautiful country. That area or fantastic. Greetings to all from Italy Tizi

    1. Hi Tizi, I’m glad you are proud of your country, Italy is beautiful and definitely one of my favourite countries in the world. Thanks for the comment

  2. Ah, Tuscany – cobblestone streets, cappuccinos, olive groves and vineyards….sounds ideal to me! Great article, Dean. And I agree that a road trip is a great way to see a place properly. Hope to get to Tuscany some day.

  3. These are some great pictures of a beautiful place! I’d love to take a trip there, it’s just a matter of getting the money and the time! I don’t want to go until I know I’ll have a lot of time there so I can see everything (well, almost everything) I want to see!

    1. I spent a whole week in Tuscany and only just got a taste of what there is to see and do there. So you definitely need lots of time if you want to see everything. Hope you can get there soon!

    1. Hi Roy, I wouldn’t say it was a mistake – I didn’t get to go to Umbria but I hear it is as beautiful as Tuscany. Anyway, you can use it as an excuse to go back to Italy 🙂

  4. I’ve been to Tuscany twice and hope to go back again. I enjoyed Florence, but also really liked Siena, Lucca, Livorno and Pisa. Next time, I’d rent a car, though, to see more.


    1. I have yet to visit Lucca and Livorno but enjoyed the other places you listed. There is a lot to see in Tuscany that you can keep going back. I recommend hiring a car, you will see some of Tuscany that you couldn’t see any other way. Thanks, Heidi.

  5. Tuscany is magic and probably one of the most beautiful regions in Italy, even if I think all Italy is amazing.
    I would also recommend Argentario where the water is always clean but very cold and Porto santo Stefano, from here is easy to get to Isola d’Elba.
    Food, wine, sun and sea. Loved it and I would definitely go back one day.

  6. It is such a pleasure reading your experience in Tuscany and all the following comments. I have been also living in several Countries and traveling for more than 15 years… but Tuscany remains for me No 1 location for its gems: food, wines, landscapes and the nice weather all year round. and people are nice :)))
    I am building a website that will sell just tuscan food and wines and we build a “hut” in the middle of the vineyards and olive groves to make special tasting or romantic dinners. Hope to have you guest there once !
    Have a look at https://i-tuscany.com if you are curious.
    I am doing my best to make the website pleasant and make it feeling in Tuscany 🙂 and of course major efforts in food and wine selection and production..

    ps: my second dearest place in the world is Sydney where i studied at Sydney Uni back in 2003!

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