Dear Traveller friends,
today I’m going to take you on the next stop of our tour around Tuscany, one of the most famous Italian lands—Chianti.

The fame of this land is mainly due to the production of the namesake wine, but Chianti is much more than wine and vineyards. In this tour, you’re going to discover beautiful medieval hamlets and stunning landscapes.

Since San Gimignano is quite near, it can be considered an excellent starting point.

If you want to discover the most significant points of interest in Chianti, your tour is going to be quite cramped. The stops are Badia a Passignano, Montefioralle, Greve in Chianti, Panzano in Chianti e Castellina in Chianti. Once finished the tour of the hills, you’ll arrive on the plane of Staggia and Monteriggioni, which is a perfect place to spend the night.

Unfortunately, there’s a stop which is challenging to include—Redda in Chianti. The program for one day is already crammed. If you want to visit this land with more leisure, you can add one day to your tour and visit Redda in Chianti too.

This is your itinerary:

Tour Chianti

Badia a Passignano

The first part of the itinerary, from San Gimignano to Badia a Passignano, is the longest of the tour and it’ll take 40 minutes more or less.

Even if this village isn’t one of the most famous in Chianti, you don’t want to miss it.

A quick stop it’s what it takes to admire the place. The village owes its name to the abbey which was built there around the year 1000. The monastery has a tormented history. Throughout the Nineteenth century, the abbey suffered several transfers of ownership, and only in 1986, the Benedictine monks managed to repurchase the monastery.

Badia a Passignano - Photo Credit: Andrea Gigliotti
Badia a Passignano – Photo Credit: Andrea Gigliotti

Unfortunately, visiting the complex isn’t easy. But you can enjoy the fascinating view of the abbey surrounded by vineyards.


Montefioralle - Photo Credit: Andrea Gigliotti
Montefioralle – Photo Credit: Andrea Gigliotti

The second stop in your tour is Montefioralle, a small district of Greve in Chianti. The distance from Badia a Passignano is short, but you’ll have to drive along some dirt roads, so be careful while driving.

Montefioralle is a very well kept small medieval hamlet. You can easily tour it on foot in half an hour. However, the small size isn’t detrimental to the atmosphere. Take advantage of the time you can spend here and savour the magic of the place. 

Greve in Chianti

After your stroll in Montefioralle, it’s time to go to Greve in Chianti, the most major centre in Chianti. The tour of the city is quite short and consist mostly in a walk around the core of the town, Piazza Matteotti.

Piazza Matteotti (Greve in Chianti) - Photo Credit: Andrea Gigliotti
Piazza Matteotti (Greve in Chianti) – Photo Credit: Andrea Gigliotti

If you are interested in wine and vineyards, Greve in Chianti is one of the best places to become cultured about the wine sector. Here you can visit the Wine Museum and learn a lot about the history and the production of wine in this land. Moreover, you’ll be able to buy some wine at the Produttori Vini del Chianti shop. Here you’ll be spoilt for choice for your souvenirs!

Panzano in Chianti

Panzano in Chianti - Photo Credit: Andrea Gigliotti
Panzano in Chianti – Photo Credit: Andrea Gigliotti

Your next stop is Panzano in Chianti. What is interesting here is the small hamlet built during the Middle Ages, which was part of a big castle. Nowadays the hamlet is, for the most part, uninhabited, but the ramparts are still visible. However, don’t expect to see a complete well kept hamlet. 

The most interesting attraction in town is the Church of Saint Mary, a small Renaissance church which is really worth the visit.

At this point, it’s probably time for lunch. Panzano offers a couple of options for a quick stop for a tasty lunch. However, if you are willing to resist for another 30 minutes, you can reach Castellina in Chianti, where you can find more places where to taste local food.

Castellina in Chianti

The village of Castellina in Chianti is probably the most charming in the whole Chianti. Partly this is due to the recent restoration works all around the town.

The hamlet is small and can be easily toured on foot. The main street is Via Ferruccio. Here you can find most of the restaurants and shops specialized in local products. Don’t miss a visit to the fortress and the city walls, which are accessible through a suggestive walkway partly underground.

Rocca di Castellina in Chianti - Photo Credit: Andrea Gigliotti
Rocca di Castellina in Chianti – Photo Credit: Andrea Gigliotti

Staggia Senese

Castello di Staggia Senese - Photo Credit: Andrea Gigliotti
Castello di Staggia Senese – Photo Credit: Andrea Gigliotti

Before reaching the last stop of your tour, Monteriggioni, you may want to make a slight detour of a couple of kilometres and reach Staggia Senese. 

Here you’ll be able to see an imposing castle, which dates back to the X century. If you want to visit the castle, you need to buy a ticket for a guided tour. During the long visit (a couple of hours at least) you’ll be able to enjoy the history of the castle and see an exhibition of contemporary art. 

Since the visit is quite long, you’d probably plan this detour only if you decide to take a two-days tour of Chianti. If you are interested, you have better book your tour of the castle at this link.


It’s time to get to the last stop of your one-day tour—Monteriggioni. This beautiful Medieval hamlet is entirely surrounded by ancient walls and shows the reminiscences of its glorious past as a dominant position over the Francigena Way. 

In case you don’t know, the Francigena Way was the route the pilgrims had to take to get to Rome or to reach Apulia and board a ship towards the Holy Land. 

Despite being a popular destination for many tourists, Monteriggioni maintained its characteristics of medieval hamlet, which makes it an unmissable stop.

Monteriggioni - Photo Credit: Andrea Gigliotti
Monteriggioni – Photo Credit: Andrea Gigliotti

Besides strolling along the streets of the hamlet, don’t miss a walk over the two accessible traits of the city wall. If you are passionate about the genre, you can visit Monteriggioni in Arme, the museum about the evolution of the siege techniques. Here you can also admire the reproductions of several medieval and Renaissance armours and weapons.

Where to eat and where to sleep

For our stop in Chianti, we decided to spend the night at the agritourism Fattoria il Casone, a few kilometres from Monteriggioni. Even if the cost for a room is slightly higher than the average (72 euros per night for a double with private bathroom) we found it a good solution for one night.

For dinner, I strongly recommend the Hotel Restaurant Casalta, in the nearby Strove. Here you’ll be able to taste the local cuisine, revisited with a modern and fresh twist. The cost (more or less 40 euros per person, wine not included) is a little higher than our usual choices. But the quality and attention to detail make it worth the price.

If you prefer, you can spend the night at the Hotel Restaurant Casalta, but the prices are more or less 50 euros higher than at Fattoria il Casone.

Now it’s time for me to conclude the post about touring Chianti.

Don’t miss our next destination in Tuscany—the Orcia Valley.

See ya!