Ultimate Chianti Tuscany Itinerary: 3 Days of Bliss


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Hills covered by expanses of vineyards, long avenues lined with cypress trees leading to old stone farmhouses with red roofs: this is the magical landscape of the Chianti  Tuscany.

A trip to the region of Chianti in Italy, among the most renowned for its wine production and culinary tradition, is an unforgettable experience, from wine tastings in historic cellars to strolling through the alleys of the ancient Chianti villages.

Here’s our 3-day Chianti Tuscany travel itinerary!

3-day Chianti Tuscany Travel Itinerary

Chianti is a renowned area in Tuscany, known for its vineyard-covered hills and beautiful stone villages, such as Castellina in Chianti. Visitors can enjoy walking along paths lined with cypress trees and tasting top-quality wines at local wineries.

Visiting Chianti in Italy is an immersion in Italian history, food, and wine culture. In this article, we propose our ‘Chianti Tuscany itinerary 3 days’ to discover one of the most beautiful areas of Italy. Are you ready to explore the sights of Chianti in just 3 days? There are so many to choose from!

Chianti Tuscany itinerary 3 days – DAY 1 – Along the roads of Chianti in Italy, San Gimignano and Siena

On the first day of our “Chianti Tuscany itinerary 3 days” to visit Chianti in Italy, we started our journey with a visit to one of Tuscany’s most famous places: San Gimignano. This charming village is world-renowned and one of the top attractions in Chianti. To avoid the high influx of tourists during peak hours, we recommend visiting San Gimignano early in the morning, late in the afternoon, or in the evening, while enjoying a delicious Tuscan dinner.

San Gimignano has ancient origins, with evidence of Etruscan and Roman settlements. However, the town’s current historic centre dates back to the Middle Ages when it was a vital transit hub for pilgrims and wayfarers along the Via Francigena.

When driving along the Chianti roads, one can catch a glimpse of San Gimignano village and its towers from a distance. The village is situated on a hill overlooking a valley covered with vineyards and olive groves. There are several car parks around the village where visitors can park their cars and start their ascent towards the historical centre of San Gimignano.

In the historic centre of San Gimignano, visitors can stroll among its 13 towers (a small number compared to the original, which is believed to have exceeded 70) and explore its most stunning squares, including Piazza della Cisterna, Piazza del Duomo, and Piazza delle Erbe. We recommend exploring every corner of the town between Porta San Giovanni and Porta San Matteo. Take a stroll through the alleys where local products are sold (don’t miss the chance to taste a good sandwich with finocchiona!) and along the walls of San Gimignano.

Another typical product at km 0 that we recommend you taste is Vernaccia di San Gimignano, a white wine produced right here and that you can easily find in any wine shop, restaurant or cellar in the village.

Visitare il Chianti - itinerario Chianti - Le Torri in pietra nel centro storico di San Gimignano - Chianti Tuscany travel itinerary

The towers in the historical center of San Gimignano

Once we had finished our visit to San Gimignano, we headed to Siena, a must-see place that absolutely belongs on the list of things to see in Chianti in Italy.

The city of Siena is world-famous for its famous Piazza del Campo, a semicircular square where the most famous palio in Italy is held every year. Just like San Gimignano, Siena has roots dating back to Roman times, but the most important development of the city took place during the Middle Ages.

The most convenient area in which to find a parking space and then walk to the historic centre of Siena is around the Fortezza Medicea and the stadium. From here you can quickly make your way through the alleys and main streets of the historic centre, such as Via dei Termini, Via Banchi di Sotto and Via Banchi di Sopra.

All these streets will slowly lead you to the famous Piazza del Campo, where you will find the famous Torre del Mangia and the Palazzo Pubblico where the Comune di Siena is located.

We were fortunate enough to visit Siena when preparations for the Palio were being made and temporary grandstands (still made of wood) were being set up around the perimeter of the square, with a long corridor running underneath to leave space for the entrances to the square. From Piazza del Campo, we advise you to head for the Duomo di Siena, which overlooks the piazza of the same name, and plan a visit inside this marvellous building.

Chianti Tuscany itinerary 3 days – DAY 2 – Chianti villages and cellars: Castellina in Chianti, Castello di Verrazzano, Castello di Vicchiomaggio, Greve in Chianti

On the second day of our ‘3-day Chianti Tuscany Travel itinerary’ focused on exploring Chianti villages, we began our tour in Castellina in Chianti. This charming village is situated in the southern part of the Chianti valley. The town’s historic centre is a pedestrian-only area that runs along the main street, Via Trento e Trieste, and leads up to the church of San Salvatore. From there, some picturesque alleys wind their way through the town.

If you arrive in Castellina in Chianti by car via the panoramic roads of Chianti, you will need to park your car along the regional road SR222. This road runs alongside the historic center of the town and leads to the main car park, which is about a 5-minute walk from the center.

We recommend walking along Via Trento e Trieste, which is lined with shops selling local gastronomic products, until you reach the church of San Salvatore. From there, continue to Piazza del Comune, which is overlooked by the Rocca di Castellina in Chianti. This building, made entirely of stone and now serving as the municipality’s seat, is an ancient fortress dating back to the 11th century and currently houses the Archaeological Museum of Chianti Senese. The Fortress was one of the first buildings constructed to defend the town centre, along with the city walls. Today, parts of the walls still surround the historic centre. Continue your walk from Piazza del Comune up to Viale IV Novembre for an enchanting view of the Chianti hills. This is also where the weekly market is held, featuring stalls full of typical gastronomic products from the area.

Via delle Volte is one of the most evocative alleys in Castellina in Chianti. It is an almost entirely covered street that passes under the stone vaults on which the houses of the historic center rest. It runs parallel to Via Ferruccio, where various shops and the Tourist Information Office are located.

Following our visit to Castellina in Chianti, we continued along the Chianti roads to our first winery appointment at Castello di Verrazzano, near the village of Greve in Chianti, for an exceptional wine tasting experience. Exploring the wines offered by the wineries in this region is a must-have experience for anyone looking to fully experience Chianti.

Castello di Verrazzano has ancient origins. It was built during the Middle Ages on the remains of Etruscan and Roman settlements. Today, it has an estate covering more than 200 hectares.

The landscape surrounding Castello di Verrazzano is incredible, with vast expanses of vineyards as far as the eye can see at the foot of the ancient residence. From its panoramic terrace, one can admire the Chianti hills. This historic winery is among the most beautiful in the Chianti region. We highly recommend booking a visit and a guided wine-tasting to sample the Chianti Classico wines on offer. The Riserva and Gran Selección are two outstanding wines.

You can also enjoy a quick lunch of mixed Tuscan crostini on the restaurant’s panoramic terrace, which is a truly fantastic experience!

From Castello di Verrazzano, we went to another nearby mansion, Castello Vicchiomaggio. This mansion is located on a hilltop, surrounded by vineyards that stretch as far as the eye can see. It is possible to stay overnight or enjoy an excellent lunch in the restaurant, which serves typical local cuisine. The wine cellar at Castello di Vicchiomaggio offers a good selection of wines, from whites to reds, including Chianti Classico, of course.

We enjoyed a superb white wine tasting in the castle garden, which boasts terraces with stunning views of the surrounding vineyards and hills.

After the tasting, we resumed our journey along the picturesque Chianti roads towards the town of Greve in Chianti. Located in the hills along the regional road SR222, the same road that passes through Castellina in Chianti, the historic centre of Greve in Chianti is situated along the main street, Via Roma. Car parks are available near the historic centre along the regional road, allowing for easy access to the centre with a short walk. We suggest walking along Via Roma, which is lined with small, typical Tuscan houses, shops, and wine bars, until you reach the main square of Greve in Chianti, Piazza Giacomo Matteotti. 

The square is entirely surrounded by porticoes, under which there are many shops selling typical local products, such as wine shops and butchers, and also restaurants with lovely outdoor areas.

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Via delle volte in Castellina in Chianti

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Chianti wine tasting at Castello di Verrazzano

Visitare il Chianti - itinerario Chianti - degustazione di vini alle cantine del Castello di Vicchiomaggio - Chianti Tuscany travel itinerary

Wine tasting at Castello Vicchiomaggio

Chianti Tuscany itinerary 3 days – DAY 3 – Radda in Chianti, Castello di Albola, Panzano in Chianti

On the third and final day of our itinerary to visit Chianti, we continued our journey of discovery of the Chianti villages with a visit to the enchanting Radda in Chianti. The historic centre of Radda in Chianti is smaller than the other villages we visited but equally charming and evocative. Its size also makes it less crowded with tourists, which is certainly appreciated.

The historic core of Radda in Chianti is nearly circular and is intersected by the main street, Via Roma, which is lined with shops selling typical products and handicrafts. Radda in Chianti is truly enchanting, and its historic centre is a typical portrait of an ancient Tuscan village. The town walls remain intact, and it is possible to take a pleasant walk with a view of the magnificent panorama that surrounds Radda in Chianti.

After our visit to Radda in Chianti, we proceeded to Castello di Albola, another exceptional Chianti winery. Castello di Albola is a well-preserved historic residence, and its estate spans over 900 hectares, partially covered by rows of vines.

It is more than just a castle; one can refer to it as a genuine medieval village, comprising of several cottages and a beautiful manor house with a marvellous garden that overlooks the valley.

Castello di Albola offers a range of experiences, including wine tasting accompanied by a visit to the cellars located in the basement, the vineyards, and an excellent lunch featuring typical Tuscan products. Castello di Albola’s top wine is undoubtedly Chianti Classico, including the Riserva and Gran Selezione versions (we particularly enjoyed the Santa Caterina). They also offer other interesting wines such as Acciaiolo and Vin Santo, as well as Albola’s extra virgin olive oil.

During our visit, we stopped for lunch in the beautiful courtyard and savoured a fantastic Tuscan sausage cooked on the barbecue.

After lunch, we headed to our final destination, the medieval village of Panzano in Chianti. The town walls have been well-preserved, and Panzano is one of the largest Chianti villages. The ‘historic centre’ is located in a small area where the Castle of Panzano and the Church are situated. We enjoyed walking through the alleyways that lead to an area where the remains of the village walls are located. From there, one can enjoy a beautiful view of the surrounding olive groves.

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View of the Tuscany countryside from Panzano in Chianti

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Among the vineyards of Castello di Albola

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Internal courtyard of Castello di Albola

In this article we have presented you our “3-day Chianti Tuscany travel itinerary” to visit this wonderful area of Italy and we hope it will inspire you to plan a trip through this magnificent land. There are countless towns and villages in the Chianti region that are worth a visit, as well as wine cellars, Italian wineries of excellence that deserve to be discovered and enhanced. Stay connected with us via the newsletter and social channels and as always… trip to try!

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