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 Siena: Dinner in the Chianti Vineyards

3. 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.

Wine Tasting and Dinner in the Vineyards of Chianti

4. 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 Florence: Tuscany Wine Tasting Full-Day Trip

5. 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 Siena: Chianti and Castles Tour with Wine Tastings

6. 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 Florence: Chianti Wine Tour with Tasting

7. From Florence: Chianti Wine Tour with Tasting

Don’t miss the chance to explore the rolling hills of the marvelous Chianti Wine region. Get away from the noise and crowds of the city and enjoy a relaxing afternoon in the world-famous Tuscan countryside. Tuscany enjoys worldwide renown for its nature, small villages, vineyards and gentle hills. Your tour starts with a visit to a rustic Wine Estate, in the heart of vineyards, where you will be greeted by the owners and offered an appetizing snack based on “crostini toscani”, home-produced olive oil, and a tasting of a delicate “Vino Chianti”. You will visit the cellar and learn all the secrets of wine processing. Your day is not over yet. In the heart of olive trees, gentle hills, and vineyards you will be offered another rich wine tasting together with some regional products, and the owners of the wine estate will teach you some easy steps to become a perfect sommelier!

Tuscany by Vespa Full-Day Tour to Chianti Wine Region

8. 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.

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

9. 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.

Chianti: Total Immersion Wine Tour with Picnic Lunch

10. 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.

Other Sightseeing Options in Chianti Hills

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

What people are saying about Chianti Hills

Overall rating

4.4 / 5

based on 6,526 reviews

Sara and Ricardo were amazing. Sara was so knowledgeable and friendly and Ricardo, our tour bus driver got us around Tuscany safely. This is a long day but perfectly organized, with many historic and beautiful sights around Tuscany, including small middle age villages and vineyards. Definitely opp for the lunch as that was one of the best parts. Great family style meal with beautiful views of the rolling hills of Tuscany. I learned so much from Sara and her local guides. Would highly recommend this one day tour.

This was an excellent tour! Angelina and Emeliano were wonderful. Yes, it was long but well with it. The bus was comfortable, they were very accommodating for the dietary restrictions for our group of 12. Definitely fed us well with seconds offered if desired. The farm tour is more a stop for photos. If you’ve seen one cow and olive tree you’ve seen them all - it is the view from the farm that is truly stunning. Highly recommend if you love small, unique Medieval towns., great Tuscan food and wine.

Sara is an incredible tour guide! Would highly recommend this tour, not only is it value for money but you also get to see what Tuscany has to offer! Would definitely complete again!

Highly recommend! The bus ride to the vineyard had incredible views and we learned about the history of Tuscan wine. Dinner was excellent and of course the wine was outstanding.

The tour was amazing. Our whole family enjoyed each part of the tour. Stefano was fun and extremely informative. We all highly recommend this tour. Enjoy!