Add dates

Things to do in Castellina in Chianti

Our most recommended things to do in Castellina in Chianti

From Florence: Chianti Half-Day Afternoon Tour

1. From Florence: Chianti Half-Day Afternoon Tour

Discover the Tuscan wine region of Chianti on a scenic guided tour by van from Florence. Visit a local wine estate, tasting its wines and local produce. Immerse yourself in the surrounding picturesque landscape, with a visit to a medieval village in the region. Visit a charming Chianti wine estate, enjoy a guided tour of its wine cellars, and gain an insight into the various stages of wine production.  You know the typical cypress avenue printed on every postcard in any gift store, right? Well yes, you will get to walk on one of these avenues and take memorable photos of authentic Tuscany. Visit a winery that not only offers a tasting that even true connoisseurs will enjoy with great pleasure, paired with samples of sliced cold meats, bruschetta, and salami, but you will also get to enjoy the wonderful surrounding landscape, immersed in an enchanting and welcoming atmosphere.  Visit a real Medieval village in Chianti hills, enjoy some free time to stroll out, and breathe in the local atmosphere. You'll also have the opportunity to buy wine, olive oil, balsamic vinegar, cheese, and herbs to take home.

From Florence: Chianti Hills Wineries Tour with Tasting

2. From Florence: Chianti Hills Wineries Tour with Tasting

Immerse yourself in Italy's renowned winemaking culture on this guided tour by van from Florence. Leave the city behind as you head out into the Tuscan countryside, marveling at the landscape around you. Visit two local wineries and enjoy wine tastings in both of them, learning about the wine-making process from locals. Arrive in the charming town of Radda in Chianti and visit one of the town’s traditional wineries. Enjoy a tasting session of 3 regional wines, then have the opportunity to purchase them. Spend some free time exploring the narrow streets of the town. Continue towards a traditional farm and winery. Learn about the winemaking process from grape to glass. Then enjoy another tasting session of 3 Chianti wines as well as local products. Finally, sit back and relax on the return journey to Florence.

From Siena: Chianti and Castles Tour with Wine Tastings

3. From Siena: Chianti and Castles Tour with Wine Tastings

Immerse yourself in picturesque Tuscan scenery on a sightseeing day trip from Siena to the region of Chianti. Visit the Castellina in Chianti before partaking in a wine tasting experience at a wine estate.   Board a spacious and climate controlled van in a centrally-located meeting point in Siena. Admire the Italian countryside on the ride as you pass thorugh pristine landscapes that have been cradling the Chianti vineyards for centuries. Discover a harmony of colors that can only be found in the hills of this region. Delight your senses as you dive into the sounds, scents, and flavors of this land will capture your senses through this unique experience.  Visit ancient churches, medieval castles, and small villages where the rhythm of life remains unaltered over time. Continues to a charming wine estate.  Indulge in a wine tasting paired with typical Tuscan food. View the beautiful ruby-red color and the characteristic bouquet with scents of violet are the special to Chianti wine. Savor this blend of Sangiovese, Canaiolo, Merlot and Cabernet Sauvignon grapes. Later, move on to another winery in the middle of the Chianti Classico area, where you’ll have a second optional wine tasting alongside an extra virgin olive oil tasting. The tour will end with a return to Siena.

From San Gimignano: Chianti by E-Bike with Wine Tasting

4. From San Gimignano: Chianti by E-Bike with Wine Tasting

There is no better way than by bicycle to discover the beauty and richness of this part of Italy, sharing in the passion for cycling, art, food and wine. The tour takes place in Tuscany, more specifically, in the magnificent landscapes surrounding Siena. There are, in fact, the most beautiful areas and also the most suitable for a cycling trip through Tuscany. From the seat of your electric bike, you will discover how Tuscany life flow slowly yet incessantly, creating a natural equilibrium among art, culture, and nature. Tuscany is paradise for a cycling tourist, who will be greeted by gently rolling hills embellished with winding dirt roads, curving pathways, vineyards, and shaded country roads. All of these splendors are framed by a surprisingly varied landscape where you will be able to discover abbeys, rural churches and castles. The landscape is characterized by the deep red earth, and alternates between fields of sunflowers and vineyards, and is punctuated by ancient castles and medieval hamlets. Many panoramic views allow you to see all the way to San Gimignano, overlooking forests of beautiful Italian oak and corbezzoli. The tour is crowned with a visit to the splendid medieval for tress of Monteriggioni. 

From Siena: Chianti Electric Bike Tour

5. From Siena: Chianti Electric Bike Tour

There is no better way than biking to discover the beauty and richness of this part of Italy, enjoying a wonderful blend of cycling, art, food, and wine. The tour takes place in Tuscany, more specifically, the magnificent landscapes surrounding Siena. They are, in fact, the most beautiful areas and also the most suitable for a cycling trip through Tuscany. Discover more about Tuscan life with its natural balance of art, culture, and nature from the seat of your electric bike. Tuscany is paradise for a cycling tourist with its gently rolling hills embellished with winding dirt roads, curving pathways, vineyards, and shaded country roads. All of these splendors are framed by a surprisingly varied landscape where you will be able to discover abbeys, rural churches and castles. The landscape is characterized by the deep red earth, and alternates between sunflower fields and vineyards, and punctuated by ancient castles and medieval hamlets. Many panoramic views allow you to see all the way to San Gamignano, overlooking forests of beautiful Italian oak and corbezzoli. The tour is crowned with a visit to splendid medieval Monteriggioni.

Florence: Private Siena, San Gimignano and Chianti Tour

6. Florence: Private Siena, San Gimignano and Chianti Tour

Explore the beauty of Tuscany in this tour from Florence to Siena, Castello di Monteriggioni, Chianti, and San Gimignano. Visit medieval towns and villages, and drive through idyllic vineyards, with the option to stop at an organic farm and winery for lunch. Meet your friendly guide at your accommodation and drive in an air-conditioned minivan to see the distinguished medieval architecture in Siena, like the seashell-shaped Piazza del Campo and Siena Cathedral before enjoying a scenic drive to Castello di Monteriggioni. Enjoy the small, fortified village and take a short stroll after lunch at one of the local restaurants. Travel along the Chianti wine road which is rich with castles and villages with a stop to admire a small medieval village surrounded by endless vineyards. Experience a unique dining setting while taking in an amazing Tuscan panorama with lunch at an organic farm in Castellina, with the lunch option. Journey to historic center of the picturesque medieval town of San Gimignano and see its ancient towers.

Chianti and Castles Tour From San Gimignano

7. Chianti and Castles Tour From San Gimignano

Immerse yourself in the picturesque Tuscan scenery on a sightseeing trip to the beautiful region of Chianti. Visit the Castellina in Chianti before enjoying a wine tasting at a winery in the area. The beautiful ruby-red color and the characteristic bouquet with scents of violet are the special features that reveal the identity of one of the most famous wines in the world: Chianti. This wine results from the wise blend of Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon grapes. On this trip, discover the breathtaking, uncontaminated landscapes that have been cradling the Chianti vineyards for centuries, presenting you with a harmony of colors that can only be found in the hills of this region. The sounds, scents, and flavors of this land will capture your senses through a unique experience. Visit ancient churches, medieval castles, and small villages where the rhythm of life remains unaltered over time. Later, move on to a winery in the middle of the Chianti Classico area, where you’ll have a wine tasting alongside an extra virgin olive oil tasting. The tour will end with a return to Siena.

From Florence: PRIVATE Siena and Chianti Classico Trip

8. From Florence: PRIVATE Siena and Chianti Classico Trip

What To Expect •Stop at: Siena, Tuscany. Siena is one of the most popular and visited places in Tuscany. It is known throughout Italy for its distinguished medieval architecture. Upon arrival, explore its rich history and art, through its notable local monuments such as the famous seashell-shaped Piazza del Campo and the outstanding Siena Cathedral. Many local shops fill the historic streets of Siena, a great opportunity for you to taste local food or buy some gifts! Duration: 3hrs •Stop At; Chianti wine Road, Tuscany. The SS222 road, better known as Chiantigiana, is one of the most beautiful roads in Italy. It passes along the entire Chianti region, from Florence to Siena. Driving on it is a great way to discover the area. You will take this scenic road going north, starting from Siena and reaching Castellina in Chianti. The area is rich with castles and villages. One example is the Castle of Fonterutoli, where you will stop to admire the small medieval village surrounded by endless vineyards, centuries-old woods, and green hills. Duration: 1hr •Stop At: Castellina In Chianti, Tuscany. This heavenly corner, hidden among the sinuous hills of Chianti, is worth a stop to visit the narrow stone streets and its characteristic historic center. Castellina also boasts a past rich in history, in fact, walking along the main road you can admire the mixed influences from Medieval and Renaissance styles. Duration: 1hr •Stop At: Organic Farm/Winery, Tenuta Casanova. (*optional) *OPTIONAL lunch at the Farm or Winery. Have lunch in a wonderful organic farm. While the owner will show you around the property, his wife will prepare a delicious and unforgettable lunch for your private group. The owner will show you to his cellar to admire his Super Tuscans and Chianti Classico wines -Craft Wine- and to the nearby Acetaia, a vinegar cellar, with old vinegar. Afterwards, experience a unique dining setting while taking in an amazing Tuscan panorama. You will taste organic specialties, such as the typical Lasagna with traditional sauces, crostini, local meats and cold cuts, legumes, seasonal vegetables, honey, and cheeses seasoned with an incredible aged balsamic vinegar. Wine will accompany this lunch every step of the wine. •Stop At: Panzano in Chianti, Tuscany. A visit in the picturesque Panzano is a must! As you take a few steps to reach Panzano’s medieval 11th century tower, you are truly immersed in another time. Enclosed by its fortified walls, you feel as if you’re returning to the Middle Ages. Take breathtaking pictures. Duration: 1hr • Stop at: Greve in Chianti, Tuscany. Experience the unforgettable town of Greve in Chianti, located in the heart of the Chianti Classico wine region, and home of the famous explorer Giovanni da Verrazzano. An unmissable visit is also due at the ancient and famous butcher shop, where you will have the opportunity to taste exceptional Tuscan snacks made with local cold cuts and cheeses!

From Florence: Private Chianti Region Tour with Wine Tasting

9. From Florence: Private Chianti Region Tour with Wine Tasting

Spend half day in the iconic landscape of the “Chianti Hills”, among cypress avenues, vineyards, sunflowers and medieval villages. Visit the historic square of Greve in Chianti and admire the wonderful village of Castellina in Chianti (probably the most typical and real of the wine villages). Later, we will taste 4/5 of the best wines of the Tuscan countryside in a typical farmhouse. This historic family has been producing the Chianti Classico for 4 generations, from 1926. You will visit the vineyards and the cellars, always in production. At the end of the explanation, you will taste 5 of the best wines of Tuscany, including the Vernaccia and the famous Chianti Gallo Nero (Black Rooster) A wonderful afternoon experience to discover the rural Chianti region, away from the city, immersed in the rolling hills of the Tuscan countryside. We will discover a village where the population still lives in the ancient stone houses of the eleventh century. We will visit Greve in Chianti and its famous square with typical products, markets, and taste the incredible wines from an ancient farm over the Chianti vineyards. Leave the confusion of the city and pass the afternoon relaxing in Chianti. This is our secret Tuscany for you!

From Florence: PRIVATE Wine Experience in Chianti Classico

10. From Florence: PRIVATE Wine Experience in Chianti Classico

Explore the flavors of the Chianti wine region on this private tour from Florence. Travel in a luxury minivan through Chianti’s unmistakable landscape of historic vineyards, rolling green hills and medieval villages... Itinerary • Stop At: Greve in Chianti, Tuscany. Experience the unforgettable town of Greve in Chianti, located in the heart of the Chianti Classico wine region, and home of the famous explorer Giovanni da Verrazzano. An unmissable visit is also due at the ancient and famous Falorni butcher shop, where you will have the opportunity to taste exceptional Tuscan snacks made with local cold cuts and cheeses! Duration: 1 hour • Stop At: Castello di Montefioralle, Tuscany. Montefioralle is truly a treasure of Tuscany - not to be missed. Originally a castle in the Middle Ages, with its 79 inhabitants, it is considered one of the most beautiful villages in Italy. Absolutely worth a visit, take time for a stroll and take some photos in its iconic, narrow stone streets. Duration: 1 hour • Stop At: Winery Brogioni Maurizio, Montefioralle, Tuscany. Here you will embark on your first wine tasting! You will be hosted by a small producer of premium, high-quality wines. The production is fully manual, from the vineyard to the wine cellar. The Chianti Classico wine is produced in an organic-certified estate. In short, this is a unique experience to taste exceptional, high-quality wine! Duration: 2 hours • Stop At: Panzano in Chianti, Tuscany. A visit in the picturesque Panzano is a must! As you take a few steps to reach Panzano’s medieval 11th century tower, you are truly immersed in another time. Enclosed by its fortified walls, you feel as if you’re returning to the Middle Ages. Take breathtaking pictures of the extraordinary southern valley, where hundreds of plots of land are planted with Sangiovese vines. Duration: 30 minutes • Stop At: Tenuta Casanova, Castellina In Chianti, Tuscany. On your last stop, it’s time for a phenomenal farm-to-table lunch and wine tasting! You will be hosted at a farm with fully organic and locally-produced products, with a wine explanation accompanying your meal. During lunch you will taste Extra Vergin olive oil, the superb Chianti Classico and the new trends of the Super Tuscan wine, white wines, dishes prepared with balsamic vinegar, and dessert wines! Animals, vineyards and olive trees will be fundamental factors in making this traditional Tuscan setting unforgettable! It will be a truly special experience for you and your private group to remember throughout the years. Duration: 2 hours

12 activities found
Sort by:

Other Sightseeing Options in Castellina in Chianti

Want to discover all there is to do in Castellina in Chianti? Click here for a full list.

What people are saying about Castellina in Chianti

Overall rating

4.2 / 5

based on 1,571 reviews

Amazing experience discovering Tuscany. Barbara is a great guide and Fiorenzo good driver. We visited a beautiful winery and enjoyed our meal and the wine testing was great. Beautiful landscapes. Would go again of course.

Really nice tour of the florence (chianti) countryside especially for its price. I didn't expect it, highly recommend.

Loved it. I recommend this tour they have amazing guides all very helpful and welcoming

Beautiful experience a smart tour that I've done without worrying about anything.

A very nice trip with excelent people! It is better to eat first before you trip!