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Things to do in Chianti Hills

Our most recommended things to do in Chianti Hills, Tuscany

From Florence: Day Trip Pisa, Siena & San Gimignano w/Lunch

1. From Florence: Day Trip Pisa, Siena & San Gimignano w/Lunch

Experience the wonders of Tuscany on one memorable day. Leave Florence for a 12-hour excursion and see the beautiful landscapes, architecture, and artworks of the region. Treat yourself to some local cuisine, and opt for a guided tour in your preferred language to learn even more about the historic area. Begin with the visit at Piazza del Campo, where the Palio di Siena horse race is run, and Piazza del Duomo, where you will see the exterior of the magnificent cathedral. After some free time in Siena you'll have lunch in a typical Tuscan winery. Then go ahead to the vineyard, where you can enjoy some local wine and visit San Gimignano, a UNESCO-listed medieval town. Continue to Pisa and to visit its stunning Piazza dei Miracoli. Admire the Baptistery, the cathedral, and, of course, the famous leaning tower.

Florence: Chianti Wineries Tour with Food and Wine Tasting

2. 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 tasting session of 4 different 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 3 wines, as the local charismatic wine producer tells you about the peculiarities of each. After some free time, head back to Florence.

Florence: Pisa, Siena, San Gimignano, and Chianti Experience

3. Florence: Pisa, Siena, San Gimignano, and Chianti Experience

Start in the morning with a tour of Pisa. Have time to admire the cathedral, the baptistery, the monumental cemetery, and the famous Leaning Tower. Then move on to a typical winery in the Chianti Hills on the slopes of San Gimignano. Enjoy a Tuscan lunch accompanied by a local wine tasting. Following lunch discover one of the most beautiful medieval villages of San Gimignano, or the "Medieval Manhattan, where you can explore the maze of cobbled streets, small squares, and many local craft stores. Continue on with a panoramic view of the Chianti countryside before arriving in Siena, where if desired, your professional guide will take you to see the most important squares, from Piazza del Campo to the cathedral, passing through the most beautiful contrade that characterizes this city. At the end of the guided tour, choose to have some free time to enjoy a cup of coffee or a panforte (a typical local cake), and to go shopping. Your return to Florence will have a gorgeous sunset in the backdrop, making for a perfect ending to an unforgettable day spent in Tuscany.

From Florence: Tuscany Day Trip with Lunch at Chianti winery

4. From Florence: Tuscany Day Trip with Lunch at Chianti winery

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: Small Group Wine Tasting Tour to Tuscany

5. From Florence: Small Group Wine Tasting Tour to Tuscany

Depart Florence and journey to the historic Chianti Classico wine region by air-conditioned minibus while your English-speaking driver explains the stunning landscape where the most famous wines from Italy are produced. Visit two wine estates, with wine and food pairings. Sample 3 of the first wine estate's wines, along with some of the fresh olive oil they produce. Learn more about the unique techniques used to produce wine and get a better appreciation of the local viniculture on a tour of the wine cellars. Continue towards the second wine estate to take a tour of the cellars and compare and contrast their techniques with the first winery. Taste different wines and olive oils produced on the farm, paired with local specialties from Tuscany, such as cheese, salami, cold cuts, and bruschetta.

From Florence: Chianti Half-Day Afternoon Tour

6. 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: Tuscany Wine Tasting Full-Day Trip

7. 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 including the renowned black rooster Chianti Classico, Brunello of Montalcino, Super Tuscan wines, along with a 30-year-old balsamic vinegar, and truffle extra virgin olive oil. 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. Enjoy the Vernaccia white wine and a Chianti Colli Senesi D.O.C.G. 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 icecream 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 Florence: Tuscany Wine & Food Tour with Guide

8. From Florence: Tuscany Wine & Food Tour with Guide

Journey through the wine-producing region of Tuscany on a guided day trip from Florence. Visit three organic wineries and enjoy lunch with a tasting of local wines, balsamic vinegar, and olive oil. Take a walk in the medieval town of Greve in Chianti. Start your day trip driving through the Tuscan countryside. Reach the first winery to learn about the winemaking process. Visit the farm, the cellar and learn all of the secrets to making wine. Next, move on to another selected hilltop wine estate, where a wine expert is waiting for you to share facts and anecdotes about the process. Sit down for a light lunch accompanied by the winery's own wines and products.  After lunch, head to Greve in Chianti, for a quick stop in the most representative village of the Chianti Classico countryside. Take some free time to admire the main square before continuing to the final stop, a historical family-owned villa and winery. Admire the views of Florence and one of the most beautiful Italian gardens in the area. Taste the winery’s local products, made with the deepest respect for the cultivation traditions of the region. Compare the products and the philosophies of these three different local winemakers.

Chianti Wine & Food Safari

9. Chianti Wine & Food Safari

With your expert guide, enjoy a comprehensive introduction to the region and its wines while touring two of the region's best wine estates. Sample the winery’s signature wines and receive tips about the art of wine tasting and pairing wine with food. First, stop at a beautiful winery belonging to one of the most prestigious Italian aristocratic families. Here, taste three wines paired with cheese and two olive oils.  Enjoy a fascinating guided tour of the historic wine cellars and to the olive mill through underground tunnels that pass under the villa.  Buckle up and get ready for some off-roading through ancient woodland and rolling hills, outlined with cypress trees and dotted with rustic farms and churches, to make your way to a typical Tuscan restaurant with stunning views.  To visit the final wine estate, go deeper into the Chianti hills and enjoy more incredible countryside on your way to a Chianti Classico vineyard.  As a contrast to the established winery of the morning, enjoy these smaller, award-winning wines that will taste of a combination of ancient tradition and innovation.  The unique beauty of this area will add to the unforgettable memories you will have created so far.

Florence: Chianti Villages, San Gimignano & Wine Roads

10. Florence: Chianti Villages, San Gimignano & Wine Roads

Journey into the heart of the Chianti region along the famous Chiantigiana Road and through a classic Tuscan landscape characterized by gently rolling hills, vineyards, silver olive groves and dotted with quaint villages. Near Greve in Chianti, enjoy a tour of a local winery with wine tasting. Here you have the opportunity to taste and buy organic extra virgin olive oil. En route, stops to get to know the area including the stunning UNESCO World Heritage Site of San Gimignano, famous for its 13 medieval towers which dominate the skyline. At the end of the visit to San Gimignano, enjoy a traditional Italian light lunch with a wine tasting, either in a wine estate or a typical restaurant producing organic wine. Throughout the day, you will travel in a comfortable car or minivan with an English-speaking driver. 

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Other Sightseeing Options in Chianti Hills

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What people are saying about Chianti Hills, Tuscany

Overall rating

4.5 / 5

based on 15,588 reviews

Wonderful trip! One of the highlights on our trip to Italy! So much information and history. We loved it! Things to note it is a LOT of walking. We walked the 10 minute walk from our hotel to the train station so that added on but we clocked over 20K steps that day. I would say we are fairly average size Americans, my husband is 5'9, I'm 5'6 the bus was a bit of a tight squeeze with no bathroom. If we had been taller or plus sized it would have been very uncomfortable.

A wonderful experience with a wonderful guide and bus driver! Barbara was very warm, friendly, and helpful and took extra measures to ensure everyone was having a nice time. She is a delightful guide and very knowledgeable! Fiorenzo is a very safe driver and got us everywhere on time with no problems. Definitely recommend!

The vans were very comfortable. Our driver was a sweetheart. Plenty of time in each area. We left a couple of areas a little early by our choice because the weather was windy and cold. Our driver came each time we called.

Went with some friends and it was the perfect combination for a wine tour that we were looking for! Two very different but both excellent wineries and both gave us plenty of wine with delicious snacks! We loved it!!

Great day, Mario was fantastic. Good amount if time to explore the towns. Would recommend to others.