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Things to do in

Castellina in Chianti

Our most recommended things to do in Castellina in Chianti

From Siena: Chianti and Castles Tour with Wine Tastings

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

Immerse yourself in the picturesque Tuscan scenery on a sightseeing trip to the beautiful region of Chianti. Explore the gardens of the Brolio Castle and visit the Castellina in Chianti before enjoying wine tasting in the Chianti 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. The tour continues with a visit to a charming wine estate. Here, you'll have the chance to see the area close to the famous Castle of Brolio and join a guided walk of the castle gardens. When the tour of the garden ends, join a wine tasting paired with typical Tuscan food. 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

2. 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. 

Florence: Private Siena, San Gimignano and Chianti Tour

3. 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

4. Chianti and Castles Tour From San Gimignano

Immerse yourself in the picturesque Tuscan scenery on a sightseeing trip to the beautiful region of Chianti. Explore the gardens of the Brolio Castle and visit the Castellina in Chianti before enjoying wine tasting at a winery in the Chianti 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 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: Minivan Chianti Wine Tasting Day Tour

6. Florence: Minivan Chianti Wine Tasting Day Tour

Discover the heart of the Chianti Classico Region. Marvel at its hilly landscapes dominated by rows of cypresses and suited to the cultivation of vines and olives. Start your experience aboard a comfortable minivan, led by an English-speaking driver. Follow the ancient Via Chiantigiana, the winding road that crosses the provinces of Florence and Siena. Relax all the way with stunning views over the Tuscan countryside. Be seduced by the timeless charm of a picturesque medieval village. Then visit two wineries and walk along the ancient vineyards. Taste superb wines of small productions that cannot be found in large-scale distribution. Also, savor extra virgin olive oil and some tasty local products.

Other Sightseeing Options in Castellina in Chianti

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What people are saying about Castellina in Chianti

Overall rating

4.3 / 5

based on 1,662 reviews

Magnifique journée en vélo électrique dans la région du Chianti. Des souvenirs innobliables: paysages à couper le souffle et repas avec dégustation de vin commentée dans un vignoble. Nous étions deux couples avec le guide alors pouvions allez à notre rythme. Une suggestion pour une prochaine fois: que les batteries des vélos soient rechargées durant le repas car la mienne était épuisée à la fin du parcours.

The tour was very nice, our tour guide was on time and explained some nice facts about the Chianti region and wines on the way. We visited beautiful privately owned Castello di Brolio and winery and then a winery in Lornano. It's a nice tour and we recommend it because it not long and starts in the afternoon at 2pm.

The tour was a lot of fun. It started in Badesse in a very well organized way. Tuscany is no problem with an e-bike. Our guide took us through several towns and the wine tasting was great. A beautiful, family-run winery. The other participants were also very nice and it was an all-round successful day.

Guide Matilda very friendly and pleasant, took us to beautiful places, all amazing! Unforgettable tour.

It was great fun…an excellent driver/guide…a great mix of people…great wine experience