Things to do in
Chianti Hills

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Our most recommended things to do in Chianti Hills

From Florence: Siena, San Gimignano & Monteriggioni Tour

1. From Florence: Siena, San Gimignano & Monteriggioni Tour

Cross the beautiful Chianti hills as you ride south from Florence in an air-conditioned GT Coach. Arrive at San Gimignano, a medieval town declared a World Heritage Site by UNESCO. Take time to wind your way through the narrow streets and admire the landscape. Make the second stop at Siena. Explore the Piazza del Campo, famous for the Palio Horse Race and for its splendid examples of Gothic civic architecture. You can also visit the magnificent Palazzo Pubblico. Finally, visit Monteriggioni and its intact medieval city walls. Then, head to the Chianti area and enjoy postcard-perfect landscapes. Conclude your day at a famous wine estate and taste fine Chianti red wine along with homemade snacks.

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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 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.

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From Florence: Pisa, Siena, San Gimignano, Chianti Day Trip with Siena Cathedral and Lunch

3. From Florence: Pisa, Siena, San Gimignano, Chianti Day Trip with Siena Cathedral and Lunch

Your day begins early in the morning with a tour of Pisa, where you will admire the stunning Cathedral, the Baptistery, and the Monumental Cemetery. Take photographs next to the celebrated Leaning Tower. Continue to a winery in the foothills of San Gimignano, where you will enjoy a typical Tuscan lunch with wine tasting. After lunch, explore one of the most famous medieval hilltop villages in Italy, San Gimignano. Discover the maze of cobbled streets, picturesque piazzas, and local artisan shops. Next, admire a panoramic view of the Chianti countryside, followed by a stop in Siena. Here, a specialist guide will lead you on a walk through the city's historical center. Skip the ticket line to see the interior of the magnificent cathedral, and pass through the shell–shaped Piazza del Campo, where the Palio horse race is held twice a year. You will then return to Florence.

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From Florence: Pisa, Siena, San Gimignano, Chianti Wine Tasting Full-Day Trip with Lunch

4. From Florence: Pisa, Siena, San Gimignano, Chianti Wine Tasting Full-Day Trip with Lunch

Discover UNESCO World Heritage Sites and taste Chianti wines on a full-day trip from Florence. Visit Pisa, San Gimignano, and Siena, and savor a traditional Tuscan lunch.  First, head to Pisa to marvel at the Piazza dei Miracoli, Pisa Baptistery, Pisa Cathedral, and, of course, the famous Leaning Tower of Pisa. Continue to a wine villa in the Chianti countryside. Enjoy a tour of the estate and learn about its history in the medieval chapel before your first tasting of Chianti Classico on the panoramic terrace. Next, relish a typical lunch accompanied by two of the estate's products, a "Riserva" and an IGP wine. After lunch, relax a while in the villa's luscious gardens before going to the medieval town of San Gimignano.  Then, follow the scenic roads to Siena for a tour of the city's monuments and piazzas. Visit Piazza del Campo — the site of the Palio di Siena horse race — and admire the cathedral's exterior in Piazza del Duomo. After some free time, return to Florence.

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From Florence: Chianti Hills Wineries Tour with Tasting

5. 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.

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From Florence: Tuscany Day Trip with Optional Lunch and Wine

6. 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.

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From Florence: Tuscany Wine Tasting Full-Day Trip

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

Join this fun day-trip made for 18 to 35-year-old travelers to the Chianti countryside by van, and discover why the area is famous for its scenery as well as its wine. 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, your first stop, where you will taste 4 different type of wines, including the famous Chianti Classico D.O.C.G. and a Super Tuscan wine, a 30 year-old balsamic vinegar, and the delicious truffle extra virgin olive oil. Here, learn how to recognize the different flavors and develop your taste buds together with a wine passionate producer. Next, drive to your second stop, a local winery located in a stunning area well-known for the production of the D.O.C.G. Vernaccia white wine and facing the famous towers of San Gimignano. Let the winemakers guide you through the vineyards and the cellars and they will share the secrets of the wine and oil production as well as the best wine and food combinations. 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.

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From Siena: Chianti Day Trip on a Vespa

8. From Siena: Chianti Day Trip on a Vespa

Cruise along scenic and peaceful roads on a Vespa. Pass through the Tuscan countryside and see working farms. Follow winding roads through chestnut woods, olive groves, and vineyards. The scenic area is also peppered with hidden relics of the past, like old castles, villages, farms, and parish churches. Keep your eye out for these as you ride by on your scooter. Enjoy this experience with your Italian and English-speaking guide, who will take you to small medieval villages situated in the heart of Tuscany. Have the chance to drive an original Vespa or decide to be driven by one of the local partner's expert drivers. The tour along the Chianti hills lasts all day. You will stop at a renowned farm for a wine tasting and delicious lunch.

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Chianti Colors & Flavors Day Trip from Florence

9. Chianti Colors & Flavors Day Trip from Florence

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. Then we move on to Greve in Chianti which is doubtless one of the most famous and best known Italian Chianti wine villages. Here you will have time to explore the characteristic alleyways and the central square with its numerous Medieval buildings and its picturesque artisan shops. Our 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!

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From Florence: Siena, San Gimignano and Chianti Wine Tasting Full-Day Trip with Lunch

10. From Florence: Siena, San Gimignano and Chianti Wine Tasting Full-Day Trip with Lunch

Enjoy a wonderful day in the Tuscan countryside, visiting the most gorgeous corners of Siena, San Gimignano, and the Chianti area. Departing from Florence, drive to the historic village of Monteriggioni. Admire the landscape of olive groves and vineyards dotted with Romanesque churches, farmhouses, villas, and castles. Continue to Siena, where a local expert guide will lead you through the city's steep medieval streets to marvel at splendid palaces. Reach the Cathedral, Palazzo Comunale, and Piazza del Campo, where the Palio race takes place every year. Make a stop at a farmhouse in Chianti, where you will taste some of the best Tuscan wines, and a tasty lunch made with local produce. Continue to San Gimignano, declared a World Heritage Site by UNESCO. The guide will lead you into the heart of the village and then you will have free time to discover the beautiful squares, buildings, and alleyways.

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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 was an excellent and affordable trip to 3 places throughout Tuscany. When I priced the train to Pisa and back, it was approximately the same cost as this trip. Our tour guide was excellent, the winery that we stopped at was very good and the host was exceedingly entertaining. I do wish we had had more time in Sienna as it was beautiful, but I understand there is a time constraint. Overall, I would highly recommend this tour.

Great trip to see a lot in a relative short time. Tuscan country side, Old towns and good food. Our guide Manolo was great, with a lot of information about Tuscany and Florence and on the way back he went past everyone to answer any questions they might had. Loved it!

Valentina was a very good guide providing all the necessary information for our day tour! We also had a very profesional driver (Raul) The tour is totally recomended! Get the one with the entrance in the Siena included! Thanks you for the beautiful experience!

Great group experience, enough time to walk around and enjoy. Would have liked more time at Pisa, maybe Pisa should be a bit longer, just a suggestion.

Very nice trip! Saw all the sights without worrying about where to go and how to get there. Would book if you get tired of having to plan out your day.