Chianti Hills

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Chianti Hills: Our most recommended tours and activities

Florence: Chianti Wineries Tour with Food and Wine Tasting

1. Florence: Chianti Wineries Tour with Food and Wine Tasting

After meeting your guide and boarding the coach, drive to the Chianti region. On the way to the first winery, your guide will share interesting facts and curiosities about landmarks along the route. Arrive at the first “cantina” of the day, where you will be welcomed by the winemakers. After listening to a brief introduction about the winery’s history and the types of wine made there, join a guided tour of the facilities and nearby vineyards. Learn all about the winemaking process, the materials used to make the barrels, and what it takes to be classified as a “Chianti Classico”. Then, begin your first wine tasting of about 5 wines. You will hear an explanation of each of the wines that you sample, as well as some tips on how to savor the wine and understand its qualities. The wines will be accompanied by local snacks produced in the region, such as cheese, bread, olive oil, and salumi. Board the bus and continue to the second winery. On the way, make a stop at a scenic lookout to observe a stunning panorama of the Chianti Hills. At the second winery, learn about their production methods, what is unique about their vines, and how weather can affect the grapes. Explore the facilities during a short guided tour, and walk through the vineyards. Then, sample another round of up to 5 wines, as the local charismatic wine producer tells you about the peculiarities of each. After some free time, head back to Florence.

From Florence: Tuscany Day Trip with Optional Lunch and Wine

2. From Florence: Tuscany Day Trip with Optional Lunch and Wine

Begin your journey of Tuscany at Florence’s central train station, where you will be greeted by your guide who will take care of you throughout the day.  Head straight to Siena, Italy’s most picturesque medieval city, whereupon arrival your guide will take you on a walking tour. Look up to admire the lovely terracotta roofs adorning the buildings and marvel at the magnificent Gothic and Romanesque architecture of the main cathedral.   Next, head to the hilltop town of San Gimignano, a UNESCO world heritage site, famous for the tower houses built in the Middle Ages. Enjoy free time here to see its splendid squares, palaces, churches, and magnificent towers. The last stop on your Tuscan excursion is a visit to Pisa and its iconic leaning tower. Take a stroll through the Piazza dei Miracoli and see other marvelous monuments, before driving back to Florence. Best of all, choose from either a small-group or private guided experience to make your trip special. Choose the lunch option to enjoy a homemade lunch paired with an informal wine tasting at a traditional wine estate in the Chianti wine region. Savor 4 regional wines at lunch and learn about their unique production techniques. Feast on an organic, farmhouse meal while you overlook the rolling vineyards under the Tuscan sun.

From Florence: Chianti Hills Wineries Tour with Tasting

3. 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: Dinner in the Chianti Vineyards

4. From Siena: Dinner in the Chianti Vineyards

A unique experience designed to give you the best of what the Chianti region has to offer: the history, the landscapes, the wine, culinary traditions, and atmosphere. Other than enjoying a delicious typical dinner of local products and dishes, you will be surrounded by the splendid and charming landscape of vineyard rows, which beautifully characterizes the Chianti region. The dishes that you will taste, all made of fresh local products, are the fruit of the hard work and care for the land that local producers have been exercising for centuries.  Upon your arrival you will be given a glass for you to carry with you on the visit of the farm’s wineries and thus enjoy a number of wine tastings on this small-scaled wine route. You will then visit the estate’s historic chapel before finally heading for dinner, the evening’s main event.  The dinner location is set to offer you maximum quality and cosiness, decorated with candles and torches. The gentle sounds of the earth and the vineyards will accompany your dinner under the stars, and a harmonious musical background, which will perfectly match the succession of dishes. You will taste pappa al pomodoro or ribollita (both typical recipes from the people’s folklore) and a barbecue of meat and fresh seasonal vegetables of the farm. Let yourself get carried away by the warmth and fragrances of the barbecue and the perfumes of the grapevines, which will enhance your dinner experience. The rural yet elegant scenery of the estate will perfectly frame and complete your evening. After the dinner you’ll be escorted back to Siena where the tour will finish.

Chianti: Total Immersion Wine Tour with Picnic Lunch

5. Chianti: Total Immersion Wine Tour with Picnic Lunch

The tour will begin you first to the rooftop terrace of the cellar from where you will be able to enjoy the breathtaking view of the Chianti Valley below and listen to the history of the estate and the territory. The estate is situated in a very elevated position for Chianti Classico ares, 600 meters above sea level. You will be able to enjoy a short description of the Chianti Classico territory, and will also see the vineyards of the estate whilst listening to the particularities of organic agriculture and what it entails. You will also hear of interesting details about the vines, the selection of the grapes, and the fertilization of the soil. You will then see the gardens of the villa as well as a vegetable garden from where the farmers grow organic produce for their cooking classes. The road then leads further to the cellar, where you will be able to see maturing wines in wooden vessels and hear about the harvest period and what it means for the production of the wines. Last but not least, the degustation room awaits you, where you will be able to enjoy 2 fresh wines as well as 3 signature wines. You will hear about each wine and chianti classico wine in general, before you receive a picnic pack with a basket if you wish, which you will be able to enjoy after you degustation anywhere on the estate.

Tuscany by Vespa Full-Day Tour to Chianti Wine Region

6. Tuscany by Vespa Full-Day Tour to Chianti Wine Region

Take a ride on the iconic Vespa, through the lush countryside of Tuscany. We will pick you up with one of our comfortable, air-conditioned mini-vans and we'll take you to the countryside, away from the busy city. In just 15 minutes you'll be at the doors of Chianti countryside. Then you will receive an orientation on how to use the Vespa safely, before we head out for our engaging and enjoyable ride. Driving at a relaxed pace along quiet and scenic country roads, you will be offered beautiful views of the rolling hillsides. We will visit different medieval villages in the heart of Tuscany and enjoy the most incredible landscapes. Next, we will stop at a 17th-century villa for a typical Tuscan meal and a guided tour of the vineyards and cellars, with wine tasting and olive oil tasting.

Wine Tasting and Dinner in the Vineyards of Chianti

7. Wine Tasting and Dinner in the Vineyards of Chianti

Embark on an experience designed to show you the best the Chianti region has to offer, including its history, landscapes, wine, and culinary traditions. Sit back and relax in an air-conditioned minivan from Florcane to an excellent wine estate, taking in the natural landscape. Discover the estate and savor its wines and fresh produce over a lavish dinner al fresco. When you arrive at the estate, grab a glass to carry on your visit to the farm’s wineries so you can enjoy a number of wine tastings along this small-scaled wine route. After the tastings, head to the leafy vineyards for dinner, the evening’s main event. Dine by the light of candles and torches, with music in the background. During the dinner, taste a number of local dishes, fresh products, and some wine and food directly from the farm. The rural yet elegant setting of the estate is the perfect frame for this memorable evening.

From San Gimignano: Chianti Half-Day Vespa Tour with Lunch

8. From San Gimignano: Chianti Half-Day Vespa Tour with Lunch

Start your experience at 11:00 AM and explore the scenic hills of the Chianti region where some of the most famous Tuscan wines are produced. Ride through the beautiful fields of vines, cypresses, and Tuscan rural houses. Enjoy plenty of stops for beautiful photo opportunities throughout your experience.  Stop at a local winery where the kind owners will escort you around their property before serving an authentic Tuscan meal, followed by wine and olive oil tasting. Hop on your scooter once again and follow your guide through the final part of the scenic ride, arriving back at the meeting point at approximately 3:30 PM.

From Florence: Tuscany Wine Tasting Full-Day Trip

9. From Florence: Tuscany Wine Tasting Full-Day Trip

Join this fun day trip to the Chianti countryside by van. Visit two local wineries and taste their flavorful wines, as well as local produce samples. Walk through the streets of San Gimignano at your own pace, discovering this charming town first-hand. Head straight to a wine tasting school to taste 4 different types of wines, a 30-year-old balsamic vinegar, and truffle extra virgin olive oil. Learn how to recognize the different flavors and develop your taste buds together with a wine producer. Move onto a local winery facing the famous towers of San Gimignano. Let the winemakers guide you through the vineyards and the cellars and share the secrets of wine and oil production. At this winery, take the opportunity to buy their local products and wine at a convenient cost to bring back home or to ship to friends and family. In the afternoon, enjoy visiting and spending time wandering through the narrow streets of San Gimignano at your own pace. Shop 'til you drop and enjoy gelato from the world-champion ice-cream making gelateria. Your departure from San Gimignano is at 3:45 PM with an estimated travel time of 1 hour and 10 minutes. You'll arrive back in Florence at about 5 PM.

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

10. 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. 

Other Sightseeing Options in Chianti Hills

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What people are saying about Chianti Hills

Overall rating

4.4 / 5

based on 6,526 reviews

This tour was the perfect way to see the Tuscan country side in one day! It’s a long day with a lot of walking but you see so many different things in a short time. Our tour guide was very helpful when needed but also let us do our own things. The winery was amazing and would have loved to spend more time there. If you are looking to get really deep into each city and spend a lot of time looking around this tour probably isn’t for you. We had about an hour to and hour and a half in each city and lunch at the winery was about an hour as well. Would recommend this to friends or family visiting!

Enrica was a great tour guide, lots of knowledge and so friendly. Wish we would have had a little less time in Siena and a little more time at the winery perhaps touring around the grounds, but this was the itinerary and no issues with the tour we went on! You still get to see tons in just one day. Overall enjoyable and would recommend.

Excellent 1-day tour to get to know the main places in Tuscany. Our guide Cristina was an excellent hostess and everything was very well organized.

Erika was an amazing guide through these beautiful cities. We enjoyed our time and discovered Tuscany. 100% recommendable.

Fast ride, but very good. The tasting is very complete, accompaniments. Great value for money.