Hey Guys! I’ve put together this guide for a road trip to the renowned Chianti wine region of Tuscany. This itinerary covers the first day of our three-day adventure, exploring beautiful medieval towns and villages in the Chianti region. Along the way, you’ll enjoy the breathtaking views of the Tuscan hills and valleys, as well as unforgettable sunsets and sunrises.
And remember, this itinerary requires a car, so make sure you’ve rented one. Let’s explore top places to visit and the best things to see in the Chianti Region. Buckle up and let’s hit the road!
1st day itinerary in four towns of the Chianti Region:
1. Greve in Chianti
We started our trip by visiting Greve. It is a charming medieval town located in the heart of the Chianti Classico wine region, 30 km from Florence on the way to Siena. The town is known as the gateway to the Chianti region.
Surrounded by vineyards and wineries, Greve in Chianti is an ideal destination for wine enthusiasts. Many wineries in the area offer tastings and tours where you can sample Chianti Classico wines and learn about the winemaking process.
Arriving in Greve in Chianti on a Saturday morning, you’ll have the opportunity to visit the local market held in Piazza Matteotti, where you can find a variety of local products such as cheese, olive oil, and wine. I would recommend trying a panino con pancetta with pecorino cheese (sandwich with pork bacon and sheep cheese); it’s just delicious and provides you with enough energy to start your day on the right note.
Greve in Chianti is tiny. Piazza Matteotti is essentially the heart of the town. Here, you can stroll along historic buildings, enjoy a cup of coffee in a local bar, and visit the Basilica of Santa Croce. Although the church itself was built in the 19th century, it contains some important artifacts such as the 15th-century painting of Madonna and Saints by Bicci di Lorenzo.
During the second week of September, Piazza Matteotti hosts the Chianti Classico wine festival. Organized by the Municipality of Greve in Chianti, this event is the only one that brings together producers from all the municipalities of the Chianti Classico region.
Just a 5-minute drive away, you’ll find Montefioralle. This picturesque medieval village is perched on a hill overlooking Greve and is known for its narrow cobblestone streets, stone houses, and panoramic views of the surrounding countryside. It’s a charming place to wander around and take some photos.
While in Montefioralle, you can visit Montefioralle Winery and take a tour of the winery, tasting some of the local wines while enjoying the view over the vineyards and the village of Montefioralle. There are several wines you can taste here, including Chianti Classico, Chianti Classico Riserva, Monteficalle, Vin Santo del Chianti Classico. You can get more information about the winery and book your visit here.
Opening Hours: 10:00 am to 6:30 pm
2. Panzano
Our next stop is Panzano, a small hilltop town located just a 12-minute drive to the south of Greve. It is another great destination to explore the beauty of the Tuscan countryside.
Panzano is also renowned for its connection to wine, with numerous vineyards and wineries in the surrounding hills producing Chianti Classico wines. The town hosts the annual Vino al Vino wine festival in the 3rd week of September, just after the Greve’s wine festival. Vino al Vino celebrates the local wine culture with tastings, live music, and culinary delights.
There are a few peculiar spots in the town worth visiting.
At Panzano’s highest spot lies the remnants of the Castle of Panzano. Emerging from a Roman settlement, Panzano thrived during the Dark Ages and is documented in various historical records. Today, remnants of the castle persist, including sections of the curtain wall and two corner towers. Notably, one tower has been transformed into the bell tower of the Church of Santa Maria Assunta. Impressively, this Romanesque church remains in pristine condition and is open to visitors today. It has a very particular facade, intricate artwork, and a peaceful interior.
Here in Panzano you’ll find the world famous Antica Macelleria Cecchini, a butcher shop and a restaurant, where you can have a very particular lunch. It is a historic butcher shop owned by the renowned butcher Dario Cecchini. Sample some of Dario’s famous Florentine’s steak, and experience the lively atmosphere of this unusual establishment. You can read more about Dario, the owner of the restaurant and a Netflix star, in our Tuscan Food Guide.
Given the popularity of Dario’s restaurants, it’s advisable to book a table in advance.
Opening Hours: 9:00 am to 4:00 pm
The price range per person, including local wine: is 30-50€
3. Radda in Chianti
Radda in Chianti is another picturesque Chianti village just a 15-minute drive away from Panzano. The town’s elevated location offers an amazing view over the surrounding Tuscan hills.
The historic center is rather small, enclosed by ancient walls dating back to the 15th century. Here, you can leisurely stroll, admiring the well-preserved town’s architecture, including Palazzo del Podestà and the 13th-century Church di San Niccolò.
The church, dating back to 1260, holds several artifacts including a canvas portraying the Madonna del Rosario with Child and Saints, attributed to Alessandro Allori. Additionally, it houses an organ from the mid-19th century. The first organ was mentioned here as early as 1634 when Giovan Battista Paolini served as the organist.
The last stop in Radda is Casa Chianti Classico for an aperitif in a rather unusual place. Casa Chianti Classico is a wine museum and wine bar located in an 18th-century convent building, offering a wine tasting experience with an amazing view over the Chianti hills from the terrace.
Opening Hours: from Wednesday to Sunday: 11:00 am – 6:00 pm. Lunch hours: from Wednesday to Sunday 12:30 pm – 2:30 pm. Dinner is currently not available.
The price range per person: 20-30€
4. San Gimignano
Our final stop for the day is San Gimignano. It is a beautiful medieval hilltop town located in the province of Siena in Tuscany. The town is encircled by 13th-century walls, offering picturesque views over the Tuscan valleys and hills.
San Gimignano is famous for its numerous medieval towers, built by wealthy families as symbols of power and prestige during the Middle Ages. While many original towers have been lost over time, several still stand today, including the Torre Rognosa, Torre Chigi, Tower Campatelli, and Torre dei Cugnanesi.
Tower and Casa Campatelli have been turned into a museum and are open for visits. The museum offers insights into the history of San Gimignano and its towers. Visitors also have the opportunity to visit the house with original furniture in the Tower.
Opening Hours: from April to October: Tuesday to Sunday from 10:30 am to 7:00 pm; from November to December: Thursday to Sunday from 10:30 am to 5:30 pm.
Ticket Price: For adults: 7€, reduced for ages 6-18: 4€, for students under 25: 5€, free entry for children aged 0-5.
The Piazza Del Duomo, the historic center of San Gimignano, is just a 3-minute walk away from Tower Campatelli. The city center is a UNESCO World Heritage Site.
Here, you can admire the beautiful San Gimignano Cathedral, dedicated to Santa Maria Assunta. The cathedral features stunning frescoes by Renaissance artists such as Domenico Ghirlandaio and Benozzo Gozzoli, as well as a magnificent Romanesque facade and interior.
Opening Hours: 10:00 am – 6:30 pm
Ticket Price (including Civic Museum): full price 17€, reduced price ( for 6-17 old) 14€, free entrance for children under 6 years old
In Piazza Del Duomo, you can visit Palazzo Comunale (Town Hall). Palazzo Comunale, also called Palazzo del Popolo or Palazzo Nuovo del Podestà, of San Gimignano hosts the Pinacoteca (Civic Museum) with important works of art from the Florentine and Sienese schools from the 13th to the 16th century, with artists such as Coppo di Marcovaldo, Lippo Memmi, Benozzo Gozzoli, Filippino Lippi, Sodoma, Pinturicchio, and Azzo di Masetto.
Opening Hours: November 1st to March 31st: Monday to Friday from 11:00 am to 5:30 pm; Saturday and Sunday from 11:00 am to 6:00 pm. April 1st to October 31st: every day from 10:00 am to 7:30 pm.
Ticket Price: Full price 9€, reduced 7€ (children aged 6 to 17, adults over 65). Free entry for children up to 5 years old.
Summary
At this point, we had completed our first day of the Chianti Tour and moved to our Airbnb in the outskirts of Siena. With plans to continue exploring the Chianti Region of Tuscany, visiting medieval towns such as Montalcino, Pienza, and Montepulciano. We decided to save Siena for the last day on our way back home. However, it makes sense to stop by this magnificent town and spend a day there on your way to the southern part of the Chianti region. Don’t forget to check out our article on the best things to do in Siena in a day. Stay tuned for the continuation of 3-day itenary to the Chianti Region in our next articles. Happy journeys!
While planning your trip to Tuscany
Check out our travel guide to Florence and find out the best things to do in the iconic city!
Florence is often considered the most beautiful city in Italy, not to say the entire world. As the birthplace of the Renaissance movement, Firenze is full of monuments, churches, museums, and sights waiting to be explored. And, of course,
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