The cutest small towns in the Chianti wine region of Italy

Chianti is one of the most picturesque areas in Tuscany. It’s one of the world biggest wine producing regions in the world and let me be honest – it is pretty damn mind blowing. I came here with my boyfriend and we drove around Chianti’s rolling hills picking grapes from the side of the road every fifteen minutes.

It takes around 2 hours to reach Chianti from Florence, and there are a number of small villages and town in the region. Here is a comprehensive list of the main places you should visit if you come here. Here’s a map of the Chianti region below:

There isn’t much in the way of public transport in Chianti; it can take over an hour to walk from one main village to another. So the best way to travel around here is by road. You can hire cars in Europe for as low as 50 Euros a day which turns out pretty cheap if you are sharing with other people. Find people to road trip with you from networks such as Instagram, Facebook traveler groups, and Couch surfing.

The main towns in the Chianti wine region are

  • Greve

  • Radda

  • Gaiole

  • Castellin and

  • Panzano

Here is a brief guide to each of these towns and the places to explore in the areas near to them:

Greve in Chianti

Greve is the main town of the Chianti Classico wine area. It hosts a number of wine festivals, which are generally held in the huge triangular piazza situated in the middle of the town. The piazza is buzzing with life; there are various wine shops, local ceramic shops, and great restaurants around it.

Just like most of the villages in the Chianti area, this place has amazing food. Some great places to eat include Villa Bordoni, Oltre il Giardino, Ristorante la Castellana, and Enoteca Ristorante Gallo Nero. Be sure to pick up a bottle of house wine and a plate of local olives – house wine is the cheapest and it will still blow anything else you’ve had straight out of the park.

Around the Greve area, you can visit the small fortified village of Montegioralle which lies on the top of a hill. You can get a great panoramic view of the area from here. There are many great wineries around the area which you can simply drive into and ask for a tour. If you go during summer, you can literally pick grapes from the side of the road.

There are a few castles situated in Greve which you can explore, such as Castello di Sezzate,  The 17th century farming estate of Vignamaggio is worth a visit to see the Tuscan way of life and learn about Italian food. Be sure to check out the Monastery in Greve as well.

The beautiful sunset through the vineyards on the way to Greven from Panzano

Radda in Chianti

This small town was my favorite of the entire Chianti region. It’s extremely picturesque and has one tiny market street running through it. Radda has a number of great wineries around it, and many of them have restaurants that offer rolling views of Chianti’s signature vineyards.

Some great restaurants to eat at in Radda include Ristorante La Bottega, La Botte di Bacco, and Casa Chianti Classico. The restaurants situated on the main street give a very homely and traditional feel and this is perfectly representative of the way they make their food. I came back here twice just to buy wine and eat.

Radda is situated on a hill between two valleys and so it offers some great sunrise and sunset views, for which you can just pull over by the side of the road and shoot. You can visit the Pallazzo del Podestra, a 15th century palace, the Church of San Niccolo, and the Fransiscan Monastery.

Nearby places to visit include the beautiful town of Volpaia, which also has some great wineries, as well as the Castello di Volpaiae. You can visit the small villages of Selvole for some more vineyard views.

Some of the best white wine I’ve had in my life was from a vineyard-cum-restaurant at the entrance of Radda in Chianti

Gaiole in Chianti

Gaiole is one of the smallest towns in the Chianti region. It hosts a rich history, having been in existence for over a 1000 years already, and has a multitude of wine shops. Check out the main square for examples of ancient Tuscan architecture.

A stream runs right through the centre of this town and there are a number of beautiful churches and castles located around this area. The largest winery of the Chianti Classico area, called Brolio Castle, is situated here. Go here to get an excellent view of the Sienne skyline.

Closeby to Gaiole, you can visit the small village of Vetrine which is a great example of the typical fortressed villages that used to exist in the Chianti area. Castello di Meleto is a huge castle near Gaiole overlooking the orchards, and Castello di Spaltenna is a monastery which was previously a castle.

Castellina in Chianti

This is definitely one of the coolest towns in the Chianti Classico areas. It has a huge underground tunnel called the Via Delle Volte which houses a number of amazing restaurants and wine shops. It also offers a great panoramic view over three different valleys.

In the main square, you can check out Rocca Castle and climb up to the tower to get a great birds-eye view of the valleys. Two castles nearby are Palazzo Banciardi and Palazzo Squarcialupi. Castellina is great to see examples of 15th century medieval architecture. Other things to do are to check out the Archaeological Museum of Chianti and the Church of San Salvatore.

Castellina in Chianti (a picturesque view of Castellina taken from the side of the road)

Panzano in Chianti

Panzano has a great location as it is situated half way between Florence and Siena, and only one hour from Florence. The town of Greve is ten minutes to the north and the other towns of Radda, Castellina, and Gaoile can be accessed in the South.

Panzano is surrounded by Chianti Classico vineyards and olive groves, making for a great place to stay and absorb the view. In the main town there are two churches within walking distance, called Pieve di San Leolino and the Oratory of Saint Euphrosynus.

Every Sunday there is an outdoor market here for various edible produce which shuts at 1pm. There are a few restaurants around the main square, the most famous one being Mac Dario, the restaurant of Tuscany’s most famous butcher.

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