Things to do in
Castellina in Chianti

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Our most recommended things to do in Castellina in Chianti

From Florence: Chianti Hills Wineries Tour with Tasting

1. 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

2. 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 and local product tastings at 2 wineries 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 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

3. 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

4. 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.

Chianti and Castles Tour From San Gimignano

5. Chianti and Castles Tour From San Gimignano

Experience the region of Chianti and immerse yourself in picturesque Tuscan scenery on this guided, multi-stop trip from San Gimignano. Visit ancient churches, medieval castles, and small villages where the rhythms of traditional life remain unaltered. Stop at 2 wineries for tours and tastings. Explore the home of one of the most famous wines in the world, with its beautiful ruby-red color and characteristic violet-scented bouquet: Chianti. This wine results from a blend of Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon grapes. Get picked up directly from your accommodation in San Gimignano, then set out to discover the breathtaking landscapes that have cradled the Chianti vineyards for centuries, presenting you with a harmony of colors that can only be found in this region. After some sightseeing, 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 you'll take part in a guided tour of the castle gardens. When the tour of the garden ends, enjoy a tasting of two different wines. During this tour, you'll see the characteristic Castle of Brolio from the outside as well as the inner garden of the castle. Later, move on to another winery in the middle of the Chianti Classico area, where you'll savor a second wine tasting paired with extra virgin olive oil. The tour ends with drop-off back in San Gimignano.

Florence: Experience Siena, San Gimignano, and Chianti

6. Florence: Experience Siena, San Gimignano, and Chianti

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.

Florence: Minivan Chianti Wine Tasting Day Tour

7. 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.

Castellina in Chianti: Dining Experience at a Local's Home

8. Castellina in Chianti: Dining Experience at a Local's Home

Immerse yourself in a private dining experience at a local's home, enjoying an exclusive cooking show and tasting authentic recipes treasured in family cookbooks passed down by real Italian "Mammas". Feel the warmth of Italian hospitality as you connect with local people. You will enjoy a 4-course menu including a starter, pasta, a main course with a side dish, dessert, and drinks included (water, selection of red and white wines from regional cellars, and coffee).

From Florence: Chianti Wine Tour with Tastings

9. From Florence: Chianti Wine Tour with Tastings

Experience the treasures of Tuscany on a guided wine tour as you travel through its countryside. Sample different local wines at two wineries paired with snacks. Get a glimpse into the traditional wine-making process with the resident winemakers. Head to the Chianti Classico and stop in a winery for wine tasting paired with snacks. Visit the picturesque medieval village of Greve, the birthplace of the famous navigator Giovanni da Verrazzano. Enjoy free time to admire the main square and browse the local artisan shops. Moving along the ancient "Via Chiantigiana," admire views of the rolling hills of Tuscany. Arrive at a family-run winery located in the Sienese area and be warmly welcomed by its resident winemaker. After the guided tour of the cellars and garden, taste four different wines paired with local snacks. Continue to Castellina, a fortified hilltop village of Etruscan origin. Walk along the medieval covered street "Via delle Volte," and follow your guide to the charming historical center with its picturesque houses, squares, and shops.

Florence: Private Chianti Tour with Traditional Tuscan Lunch

10. Florence: Private Chianti Tour with Traditional Tuscan Lunch

Explore the rolling hills and classic tastes of Tuscany on this day-trip tour from Florence. See gorgeous villages and wineries, and eat a typical Tuscan lunch as you tour the Chianti region. Climb into your comfortable, air-conditioned vehicle for a trip into the country. Take advantage of free WiFi as you pass through the green landscapes of this beautiful region. Admire churches and medieval hamlets as you drive along the Via Chiantigiana to Castellina. Fall in love with this medieval village and its majestic Rocca. Enjoy the family atmosphere of two wineries and sit down to a traditional Tuscan lunch. Enjoy truffles, cheese, and other delicious local produce, all accompanied by six matching wines.

Frequently asked questions about Castellina in Chianti

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What people are saying about Castellina in Chianti

Overall rating

4.4 / 5

based on 496 reviews

Great Wine Tour to the Chianti region. Visited 2 wineries tasting 3 wines at each stop. Lots of good information about the production and the stages to wine tasting, colour, aroma and taste! Shame we had such poor weather as it meant we couldn’t be outdoors very much. We also stopped and explored the little town at our 2nd stop, had time for a coffee and cake before returning to Florence. Our guide and driver were excellent. Would recommend the trip.

Such an amazing tour diving into the beautiful Tuscany scenery, two short stops at pre-medieval towns Grieve and Castellina were big pluses. And of course the Chianti wine tasting in two wineries, we absolutely loved the tasting at Piggio Amorelli. We didn't have enough time for a full day tour, so this is a perfect option!

Daniel was an excellent guide, we enjoyed every stop of the tour and look forward to recommending it to our friends.

Great experience and really nice, even got me a birthday cake which was very thoughtful. Absolutely loved it.

Great option if you don't have an entire day to dedicate to wine tasting and exploring.