Visit Chianti in 7 Days: Itinerary and Tips

The Chianti region is one of the purest expressions of Italian beauty, a place where the culture of wine has shaped the landscape and etched itself deeply into history. Discover it with our complete guide to visiting Chianti in seven days.

Holiday in Chianti: one week itinerary

When we started planning our vacations in Italy, we were looking for a place that combined relaxation, culture, food, and wine. Chianti was the perfect answer: we could see ourselves among sun-kissed hills tasting ruby red glasses of wine.

And of course, Chianti was all this and much more. This corner of Tuscany cuddled us with its full-bodied wines and tasty dishes and told us its many stories through villages and wineries. If you dream to visit Chianti but you don’t drive a car, remember that there are plenty of guided tours of the wineries that depart from Florence.

So, what to do in Chianti in a week? Here are our itinerary and lots of tips on the best wineries to visit, where to stay, and where to eat in this area.

• Day 1: Castellina in Chianti
• Day 2: Radda in Chianti and Castello di Albola
• Day 3: Siena
• Day 4: Greve in Chianti, Montefioralle and Castello di Querceto
• Day 5: San Gimignano
• Day 6: Gaiole in Chianti, Vertine, Castello di Brolio and Badia a Coltibuono
• Day 7: Volterra
• Day 8: Monteriggioni
• Chianti Classico and the legend of the Black Rooster
• Where to stay in Chianti
• Where to eat in Chianti
• How to get around Chianti

Day 1: Castellina in Chianti

Our Chianti tour starts in Castellina in Chianti, where we stayed for a week at the Hotel Colle Etrusco Salivolpi. We will tell you about it later.

The historic center of Castellina is small but quaint, full of restaurants and stores. Our favorite spot is Via delle Volte, a covered walkway in the fortified walls. For a romantic dinner, we suggest you stop at the restaurant Sotto le Volte.

Not to be missed in Castellina in Chianti are also the medieval church of San Salvatore and the Rocca, now home to the Archaeological Museum of Chianti Senese. From its terrace, you can admire an enchanting panorama, while during the summer the square comes alive with an outdoor cinema.

Day 2: Radda in Chianti and Castello di Albola

The second day of our tour is dedicated to Radda in Chianti. This walled village is full of stores, alleys, and squares. Among the strings of clothes hanging and colorful doors, it’s impossible to stop taking pictures.

The Palazzo del Podestà is the most striking building, with its ancient coats of arms embedded in the facade. On the same square, there is the Prepositura di San Niccolò, a church dating back to 1200 (under restoration at the time of our visit).

Discover the Chianti hills on board of a Vespa with this tour

After a walk in Radda, we drive up to the Castello di Albola for a visit to its cellars followed by wine tasting and light lunch. We go up for gentle curves among rows of vines until we see the castle.

This historical estate is now property of the Zonin family, who dedicated themselves to the restoration of the structure, to the enlargement of the vineyards and, of course, to the production of Chianti Classico wine.

The guided tour lasts about an hour and takes us through the cellars, where we learn more about the production of this wine. From the private collection, we go to the beautiful inner courtyard for a tasting with light lunch. When we leave we are a little bit tipsy but very happy.

Castello di Albola: tours and prices

• Reservation for tours is recommended
• Different tours and wine tasting from €20
• Visit of the vineyards and tasting of 4 wines with 4 typical tuscan courses, €35 per person
• Website 

Day 3: Siena

For our third day, we leave behind the delights of Chianti Classico and set out to discover Siena. This medieval city is famous for its Palio, a horse race held twice a year (on 2 July and 16 August), where the contenders represent ten of the seventeen districts of the city. 

We are lucky: we happen to be there in the same period when the Cathedral’s floor is uncovered. Every year, in fact, the marble floor of the Siena Cathedral is exposed for a limited period. We get lost in contemplation of its carpet of marbles, with scenes created by the greatest Sienese artists.

We also visit the Piccolomini Library. This wing of the Duomo was built by Archbishop Francesco Piccolomini Todeschini (later Pope Pius III) to house the immense book collection of his uncle Pius II.

The walls are completely frescoed by the Italian painter Pinturicchio, based on a preparatory drawing by Raffaello: a marvel without end.

Siena Cathedral: opening days and prices

• Opening hours
• All inclusive Opa Si Pass from €8 to 15 depending on the period
• The Gate of Heaven All inclusive €20
• Online booking

After visiting the Duomo, we head towards Piazza del Campo, the heart of Siena, on which stands the austere Torre del Mangia. Our hearts beat fast in front of such beauty.

It’s time to spoil ourselves with a luxurious lunch. We choose Tar-tufo, a restaurant a little outside the center that seduces the eye and conquers the palate. We’ll tell you more about it later.

After leaving Siena, we spend the afternoon relaxing by the pool. Later on, we get back in the car to reach Panzano in Chianti and walk through the streets of the village.

It is now dusk, and there are only locals around: children playing, a woman watering her flowers. It feels so out of time as if crystallized in a spell of immobility.

In recent years, a place has contributed to Panzano’s fame: we are talking about Antica Macelleria Cecchini, which was featured in an episode of Chef’s Table. The owner, Dario Cecchini, is known for his eccentricity: for example, he is used to reciting the Divine Comedy while preparing steaks.

Day 4: Greve in Chianti, Montefioralle and Castello di Querceto

We go back to Chianti to spend our fourth day discovering villages and wineries. Our first destination for the day is Greve in Chianti: here we stroll around Piazza Matteotti, surrounded on two sides by arcades and stores.

At the center of the square, the statue dedicated to Giovanni da Verrazzano reminds us that the famous explorer of the Bay of New York and Canada was born in Greve in 1485. You can’t miss the Antica Macelleria Falorni, active since 1729: the perfect place to taste Tuscan cold cuts and meats among chopping boards and sandwiches.

But then the rain starts falling and we are forced to take shelter in the car. We drive a few kilometers uphill to reach Montefioralle, one of the most characteristic villages of Chianti. Another celebrity of the explorations, Amerigo Vespucci, was born here.

We wait for the sky to open up to wander in the alleys of Montefioralle. On the cobbled streets, the sun slowly dries the rain, the stone houses display the most beautiful plants and flowers, the hills are green with vineyards…

We leave the narrow streets of Montefioralle to drive towards our second Chianti Classico tasting at the Castello di Querceto. When we enter the courtyard of the castle, an out-of-tune violin plays from the windows of the manor house and two peacocks wander around among the visitors. It’s a timeless experience. 

Built on the ruins of a medieval castle, since 1897 Castello di Querceto has belonged to the François family, who made it the base for their production of Chianti Classico. We visit the cellars and the private collection of the castle, then sit down for the tasting. Of course, we do not leave without buying a bottle of wine.

Castello di Querceto: tours and prices

• ‘The Classico visit’ guided tour and wine tasting €10
• Online booking

Day 5: San Gimignano

Once again we leave the Chianti Classico region for a day trip to San Gimignano. This towered city is no more than 45 minutes away: an opportunity too good to miss. After the quietness of the countryside, the medieval town appears crowded with tourists, but still enchanting.

The historical center of San Gimignano is a UNESCO Heritage Site and its skyline is unique in the world. In fact, the ‘Manhattan of the Middle Ages’ preserves fourteen medieval towers out of the original seventy-two. The oldest tower is called Torre Rognosa, while the highest one is Torre Grossa (or Torre del Podestà).

We take a lot of pictures in Piazza del Duomo and Piazza del Podestà, then go up to the Rocca di Montestaffoli to admire the view and walk along the ancient walls. We grab a sandwich in one of the many stores, then we queue up at Dondoli‘s, to taste their world champion ice cream.

Before heading home we stop at a wine shop and buy a bottle of Vernaccia di San Gimignano, the fresh white wine produced from an indigenous grape variety.

Day 6: Gaiole in Chianti, Vertine, Castello di Brolio and Badia a Coltibuono

Chianti Classico never ceases to amaze us: on day six of our tour, we visit Gaiole in Chianti. The town is linked to a historic cycling event, L’Eroica, which since 1997 evokes the cycling of the past on vintage bikes and dirty roads.

A couple of kilometers from Gaiole we make a stop at the Pieve di Santa Maria a Spaltenna, which dates back to the year 1000. Unfortunately, the church is closed for restoration work, while a luxurious resort, named Castello di Spaltenna, has been built next door.

We continue in the direction of Vertine, a fraction of Gaiole. Its castle is mentioned in a document of 1013, testifying the antiquity of the settlement. Today the small walled village is completely restored and enchants with its silent alleys.

The castle of Brolio between wines and legends

It is almost lunchtime, but we want to touch one last stop. We head towards Castello di Brolio, whose history is strictly connected to the history of Chianti Classico. The castle has medieval origins and many times played a leading role in the territorial dispute between Siena and Florence.

However, the story that interests us most closely begins with Baron Bettino Ricasoli, who during the nineteenth century transformed the castle according to the Gothic revival style of the time. Ricasoli, called the Iron Baron, was an important politician and the second Italian Prime Minister in 1861.

Baron Ricasoli became interested in viticulture, creating in 1872 the modern recipe of Chianti wine. According to the legend, his ghost still roams around the castle on horseback.

Today Castello di Brolio remains connected to wine: Ricasoli winery, in fact, owns the highest number of hectares of vineyards in Chianti Classico. Besides wine and its legendary aura, a good reason to visit Brolio Castle is its amazing view. From the walls of the castle, you can glimpse the profile of Siena and vineyards as far as the eye can see.

Castello di Brolio: opening days and tours

• Opening days and hours
• Book your tour

Badia a Coltibuono

The time has come for our last tasting in Chianti Classico. We are at Badia a Coltibuono, an abbey founded in 1049 and today converted into a luxury B&B, restaurant and winery.

Vallombrosian monks were the first to cultivate vines on these lands. Today the abbey belongs to the Stucchi Prinetti family, specialized in the production of organic wines.

After visiting the cellars and the ‘Library of wine’ (this is how the private collection is called), we are accompanied in the lush garden and finally in a frescoed room for the tasting.

Badia a Coltibuono: tours and prices

• Guided tours everyday in the afternoon
• Guided tour and tasting of 2 wines, €10
• Website

Day 7: Volterra

We are almost at the end of our holiday in Chianti. We decide to dedicate a day trip to Volterra, a beautiful medieval city with Etruscan origins.

Driving towards Volterra, we are struck by the primordial beauty of the Val di Cecina hills. Here and there the eye catches sight of monumental geometric sculptures: Land Art projects by the Italian sculptor Mauro Staccioli, located in strategic points of the territory.

Our tour of Volterra begins in the medieval alleys around Piazza dei Priori and the Duomo. The Palazzo dei Priori bears an impressive resemblance to the one in Florence, except for the coats of arms decorating the facade.

We visit the Guarnacci Etruscan Museum, the second most important in Italy after the one in Rome. Its collection of cinerary urns is endless: it’s almost like walking through an immense Etruscan cemetery.

But the star of the museum is a subtle and mysterious statuette, called ‘Ombra della Sera’ (Evening shadow). This votive bronze owes its poetic name to the writer Gabriele d’Annunzio: its sinuous forms have something very modern about them.

Volterra is also the city of alabaster. There are many workshops in the city that carry on the traditional working of this precious material. A small exhibition area attached to the Civic Museum is also dedicated to alabaster.

If you are an art lover, we suggest you stop by the Civic Museum to pay homage to the masterpiece of its collection: the ‘Deposizione’, by Rosso Fiorentino, a master of Mannerism.

Not to be missed is also the Roman Theatre of Volterra, rediscovered in the 1950s and dated between the first century BC and 13 AD. Part of the stage and cavea is still visible: you can admire an evocative view from above from Via Lungo le Mura del Mandorlo.

The Volterra Card is an excellent tourist pass to visit the city. With only €16 you can access all the sites of interest in the city, including the Palazzo dei Priori, the Etruscan Museum, the Civic Museum, the Alabaster Ecomuseum and the Roman Theatre.

Day 8: Monteriggioni

Even the most beautiful things come to an end sooner or later. Reluctantly, we have to pack our bags, check out of our hotel and leave the Chianti hills behind us.

The last stop on the way home is Monteriggioni, a popular location for movies and videogames, such as Assassin’s Creed. The small fortified village is still completely surrounded by walls and fifteen mighty towers.

Inside the walls, you can find Piazza Roma, with the Church of Santa Maria Assunta. The intense summer heat forces us to a short visit, but the enchantment of this village remains unchanged.

Then we head towards the nearby Abbadia a Isola, an abbey founded in 1001 along the route of the legendary Via Francigena. During the Middle Ages, this road led pilgrims and crusaders from Canterbury to the Holy Land, passing through these areas as well.

The last lunch of our holiday is worth a mention. We say goodbye to Tuscan cuisine at the cozy Cantinale restaurant. Pappa al pomodoro and pici with meat sauce are a good way to say goodbye to Chianti… at least for the moment.

Chianti Classico and the legend of the Black Rooster

Chianti is an area of the Tuscany region included in the provinces of Florence, Siena and Arezzo. Its hills covered by vineyards and olive groves have made this landscape famous all over the world.

Within this territory we can distinguish the smaller area of Chianti Classico, where the homonymous wine is produced with Sangiovese grapes for 80-100%. Chianti Classico includes the towns of Castellina in Chianti, Radda in Chianti and Gaiole in Chianti.

The symbol of Chianti Classico wine is the black rooster visible on all bottles.

According to the legend, in medieval times Florence and Siena disputed this territory. In order to settle the dispute once and for all, two knights would have to leave at dawn from their respective cities and meet halfway, using the cockcrow as a starting signal. The point of their meeting would have marked the border.

The Sienese chose a white rooster, while the Florentines chose a black one, which they kept fasting for several days. Exhausted by hunger, the black rooster began to crow well before dawn, giving a large advantage to the Florentine knight.

When they met, the Sienese had covered a distance of only 12 km, and all of Chianti passed under the leadership of Florence.

Where to stay in Chianti: Hotel Salivolpi in Castellina in Chianti

For our vacation in Chianti, we chose to stay in Castellina in Chianti, an ideal spot for exploring the area and the surrounding art cities, such as Siena, San Gimignano and Volterra.

We spent a week at Hotel Colle Etrusco Salivolpi, a beautiful property in rustic Tuscan style with a garden and a pool. We loved it for its outdoor breakfast and romantic atmosphere.

Between a book and a spritz, we relaxed like never before. For a week in the high season, we spent about €900.

Where to eat in Chianti

During our trip, we experienced the richness of Tuscan cuisine. Here is a list of recommended places to eat in Chianti.

Enoteca Nuvolari, Castellina in Chianti

Tasty traditional dishes and wines of their own production. Try: potato ravioli with wild boar sauce and pici cacio e pepe.

Osteria Pastececi, Castellina in Chianti

Excellent restaurant that rethinks traditional specialties in new combinations, such as zucchini flowers stuffed with cod or Cinta Senese fillet with tzatziki sauce.

Sotto le volte, Castellina in Chianti

The Tuscan tradition in all its power, in the picturesque setting of the covered walkway of Castellina. The cutting board with Italian bruschetta and local cured meats is simply spectacular, as are the homemade tagliolini with truffles.

• Website

La Chiantina, Castellina in Chianti

More excellent traditional dishes and wines by the glass. Try the gnocchi with pecorino cheese and truffle and also pici cacio e pepe with guanciale and fresh fava beans.

• Website

Ristoro di Lamole, Greve in Chianti

The most beautiful sunset of Chianti appears after 8 km of dirt road between woods and vineyards. At Ristoro di Lamole we tasted the Florentine steak for the first time. The zucchini pie with pecorino sauce and fresh truffle was also a sublime appetizer.

• Website

Antica Macelleria Falorni, Greve in Chianti

In Chianti, butcher shops are no longer the same as they once were: some have been transformed into fashionable establishments, like Antica Macelleria Falorni. Fortunately, the quality of the raw materials has not been compromised: tasting a Chianina beef tartare is a heavenly experience. There are also good veg alternatives, such as panzanella.

• Website

Badia a Coltibuono, Gaiole in Chianti

The perfect restaurant to taste traditional dishes prepared with local organic ingredients. The outdoor tables under the pergola are enchanting.

• Website

Tar-tufo, Siena

To celebrate a special occasion we were looking for a unique location. If the interior of Tar-tufo is almost intimidating in its sophistication, the kitchen is an explosion of surprises, from the chef’s welcome to desserts. Reasonable prices for the quality.

• Website

Panineria Al Vicolino, Volterra

Tuscan street food at its best: at Al Vicolino the list of ingredients to stuff a sandwich is practically endless. Excellent quality, worth queuing for.

Cantinale, Monteriggioni

Further down from the fortified village, Cantinale is the restaurant of Fattoria Castello di Monteriggioni. Tuscan specialties are prepared in a traditional and tasty way; the place is really cozy and the prices are below average.

• Website

Wineries to visit in Chianti Classico

Besides the wineries we visited (Castello di Albola, Castello di Querceto and Badia a Coltibuono), Chianti Classico offers endless possibilities to wine lovers. It is practically impossible to drive two kilometers without running into a “wine tasting” sign.

Here are other excellent wineries in Chianti to visit. 

• Tenuta di Fonterutoli (Castellina in Chianti);
• Castello di Verrazzano (Greve in Chianti);
• Castello di Brolio (Gaiole in Chianti);
• Rocca di Castagnoli (Gaiole in Chianti);
• Castello di Ama (Gaiole in Chianti);
• Antinori nel Chianti Classico (Bargino).

How to arrive and how to move around in Chianti

For our week in Chianti, we chose to travel by car, the most comfortable way to get around the various villages.

Driving in Chianti does not require any particular attention, except for the patience to endure steep bends, climbs and descents. And, it goes without saying, never drive right after a wine tasting.

It is also possible to visit Chianti without a car, for example by renting a scooter or an electric bike. There are also guided tours to the wineries from the main cities in the surroundings: read this article to learn more.

Here we are at the end of our guide to visiting Chianti in 7 days. If you are planning a trip here and still have questions, leave a comment.