The cutest towns in the Chianti region in Tuscany

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Latest update: 20 June 2023

The Chianti region of Tuscany is beautiful, stunning even. It is not only the endless supply of wine that attracts but also the mountain roads with their unpredictable curves, the abundance of poppies, and the views filled with endless green hills. Car trips through the Chianti region are a joy. This is the Tuscan countryside at its best. Drive from town to village, and you can’t help but fall in love with Chianti.

The best towns in Chianti, Italy

The Chianti region is a wine region between Siena, Florence, and Arezzo. The area is dotted with vineyards and small villages. Every town has its own charm. There is always a central square and a church. Many towns are so small that you’ll pass through them in the blink of an eye. Winding roads lead you from one village to another. The navigation system sends me over impassable paths that require you to turn around regularly – thanks, Google. We’re not the only ones: a few other tourists also rely on Google. But it does not matter! I’m in Chianti, and I love it. Let’s explore some of the best towns in Chianti!

Tip! Rent your car at Sunny Cars. You rent all-inclusive, so you can just skip all those extra insurance policies that they try to sell you at the counter. EasyTerra is also a good option.

Cute Chianti town: Castelfiorentino

Castelfiorentino in Tuscany is a small village where there is actually very little to do. When the Giro D’Italia passes through, the town turns pink. But otherwise, it is pleasantly quiet. There is a train station, a small center with some restaurants (go eat pizza at O’Vesuvio!), and nature. The Via Francigena, the famous pilgrimage route, runs past Castelfiorentina.

Two wonderful people live in the village of Castelfiorentino: Ania and Maurizio. And you can sleep with them. No, no. Not like THAT. You can sleep at their place. Their agriturismo Brotafalchi is amazing. There are two cottages, a covered wagon, and a tent to sleep in. Maurizio plans to add one or two more small-scale accommodations. My plan was to sleep in the tent, but it’s freezing cold when I arrive. I’m not really looking forward to the night, I must say. But the couple is way ahead of me and gives me the cottage to stay in. I’m super thankful! Also for the company: Ania has many stories to tell, while Maurizio jokingly plays the oppressed Italian husband.

If you want, you can dine at Brotafalchi. I recommend that you do this at least once. Ania and Maurizio do their very best, and the portions are huge. These two know how to pamper their guests: a cup of coffee here, a piece of cake there. Keep the holiday vibes coming in Castelfiorentino!

You’ll find Agriturismo Brotafalchi in the Tuscan countryside. It gives you easy access to the Francigena. You’ll get to the next village in 50 minutes if you follow it to the right. You’re mainly doing this for the walk and the scenery, as the town doesn’t offer much entertainment. Just a church with a garden to catch your breath. You can write down your wish or dream for the future and drop it in the letterbox. On the way, you pass the winegrower who also supplies Agriturismo Brotafalchi. Maybe you can pop in to see if they’re open for a visit.

You can book the cottages of Agriturismo Brotafalchi via Booking.com and the tent and the covered wagon via Airbnb.

Certaldo in Chianti, Tuscany

Certaldo in Italy actually consists of two parts: the new part and the old (Certaldo Alto). The two are literally and figuratively separated from each other. Certaldo is relatively modern, and Certaldo Alto has a medieval vibe.

Certaldo is at the bottom of the hill, and Certaldo Alto is at the top. You can get there by car or cable car: park for free at Piazza Boccaccio and take the cable car from there. The new town is not that special, although you can stop by the Jam Café (Google Maps location) next to the station for a coffee and a croissant.

It’s actually all about Certaldo Alto. The old part consists mainly of Via Boccaccio. This is the main street with a handful of shops and restaurants. At the end of the road is the Palazzo Pretorio. You can also get married there, which is why I’m in Certaldo. As a visitor to a wedding – just to be clear. 😉 It is a beautiful setting, between the red brick and the ancient houses decorated with flowers. Even in the rain, the town is charming!

Panzano in Chianti

On the way to Panzano in Chianti and in the village itself, you will see small drawings on road signs, walls, and other spots. This is the work of a local artist, and now you know: you’re headed in the right direction!

Panzano in Chianti is probably my favorite town in the Chianti region. I stayed for five days to discover the area. After five days, you have literally seen every street tile fifteen times: it is a tiny village. But oh so beautifully situated between the hills. As a casual passer-by, you’ll be done with Panzano in half an hour. But, there is more to experience in Panzano in Chianti than you think, for those who take their time.

You can go on excellent hikes in the area, but the real highlight is butcher Dario Cecchini. This local celebrity has no fewer than three restaurants in town. Simple restaurants where it’s all about meat. Dario calls himself a butcher who cooks instead of a cook. Be sure to stop by the Antica Macelleria Cecchini butcher shop. If you have more time, try the restaurants too. I’ll tell you more about them in this blog. It also contains more tips, such as a walking route, cafes, etc.

Greve in Chianti

In Panzano in Chianti, it’s butcher Dario who holds sway; in Greve in Chianti, it’s the Falorni family. Antica Macelleria Falorni on the large funnel-shaped square Piazza Matteotti is the place to be.

Greve in Chianti is on the route of quite a few organized bus trips. Fortunately, the central square has many outdoor cafés below and above the arcade arches. The village has few attractions, but as with all towns in the Chianti region, a short walk through the streets is always a good idea to get a feel of the place. After, settle down at Antica Macelleria Falorni for a glass of wine, homemade salami, delicious hams, and a steak tartare. Feast!

Website Antica Macelleria Falorni

Winery Antinori is also located in Greve in Chianti, outside the center. This ultramodern winery is definitely worth a visit. However, it is not as authentic an experience as with a local winegrower – everything is spotless and perfected to the last detail. So you mainly go for the architecture and the wine, not the atmosphere. Read more about wine tasting at Antinori.

San Gimignano in Tuscany

San Gimignano is known for the 14 towers that rise above the village. It’s the Manhattan of Tuscany. And apparently, the whole world knows that. Even on a stormy day, San Gimignano is crowded. The medieval village is ruined by its own success. There are many souvenir shops, and you pay the top price for a cup of coffee.

I try to avoid the main street a bit, ending up in pleasant streets. But no, the charm is gone thanks to the tourist overload (and yes, I know I’m one too). As far as I’m concerned, this is not a must-visit for your road trip through the Chianti region, or maybe a speedy one.

First published: February 2020. The article has been updated since.