Chianti Hills
Neighborhood Tours

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Our most recommended Chianti Hills Neighborhood Tours

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

1. 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: Chianti Hills Wineries Tour with Tasting

2. 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: Chianti Wine Tasting Day Trip with Food

3. From Florence: Chianti Wine Tasting Day Trip with Food

After departing from Florence, drive to a charming wine estate in the Chianti region. Join a guided tour of the wine cellar to learn about the various stages of wine production. Sit down and taste the various wines that the winery produces, paired with samples of sliced cold meats, bruschetta, and salami. Then, visit a medieval village in the Chianti hills, with some free time to stroll around and take in the laid back local atmosphere.

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Florence: Tuscany & Chianti Classico Trek & Wine with Lunch

4. Florence: Tuscany & Chianti Classico Trek & Wine with Lunch

Spend a day walking in nature where local wines and food are combined to have a marvelous day out in Tuscany through natural beauties, historical small wineries, and little villages nestled in the heart of the Chianti wine region. Understand the process of wine-making and olive oil production. Hop on a minivan and be driven along unique little roads in the Chianti Classico wine region. Reach the starting point located in Panzano in Chianti. The exact drop-off point is a secret. Start the day with a little walk through the Conca d'oro, a magnificent natural Amphitheater where the best Chianti Classico wines are produced. Walk through vineyards leading you to the first winery stop. from the 12th century, run by a local family. At this family-run winery from the 12th century, visit the wine cellar. This is the second oldest building in Panzano in Chianti, used as a medieval post. Enjoy marvelous wines and food tasting in a stunning historical location. Say goodbye to this unique wine cellar and continue walking through olive groves and vineyards toward the second winery. Savor lunch and another wine tasting (sometimes the lunch is postponed to the next stop). The marvelous wine here is produced by 3 generations of local farmers. Tuck into a tasty Tuscan lunch with a selection of their wines, perfect to recharge for another hike towards the last winery. The last Winery is a modern winery created by Italian artists. Settled right at the top of the hills overlooking Montefioralle, an enchanting castle nested in a great position. In the last winery, all modern techniques are combined with old, time-tested knowledge. Enjoy the last wine tasting here. For those who want to hike more, there is the final stretch downhill to reach Montefioralle. Get on the minivan back to Florence.

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From Florence: Private Full-Day Jewels of Tuscany Tour

5. From Florence: Private Full-Day Jewels of Tuscany Tour

Be seduced by the eternal charm of Tuscany’s jewels on this 12-hour tour. What are Tuscany’s jewels? The beautiful cities and villages, as well as art and the historical monuments that call this unique region of Italy home. Falling in step with the more ‘human’ way of life in Tuscany, this relaxed tour begins when you want it to. You determine the pick-up time from your centrally-located Florence hotel. You will also enjoy the transportation, which is provided by a private vehicle operated by an English-speaking driver. After pick-up, you will drive through the Tuscan countryside until your first stop, Siena, is reached. Siena is a medieval city known for its artistic treasures, which have been recognized by UNESCO. In Siena you will visit the shell-shaped Piazza del Campo. Here you will find the Palazzo Comunale flanked by the Torre del Mangia. Every year the famous Palio takes place here. You will also have free time to visit the cathedral, built in the Middle Ages and admire the splendid buildings and narrow streets. From Siena, you will enjoy a drive through Chianti territory on your way to Monteriggioni. The drive boasts a panoramic view of the vineyards and olive groves. Monteriggioni is a small 13th-century town which is still surrounded with its original town walls. Here you will take a walk within the restricted perimeter of the walls, which have eleven towers with spectacular views. This is a Tuscan gem that will transport you back in time. Only a short distance away, in a pleasant country estate you will be served a typical Chianti-region lunch. You will also enjoy a guided tasting of Chianti and Vernaccia wines. After lunch you will leave the estates and go to San Gimignano, another beautiful town and UNESCO world heritage site. Famous for its signature medieval town planning, it is called the “Manhattan of the Middle Ages”. On a stroll through the town center you will discover the Piazza della Cisterna, the Dome, the Palazzo del Podestà and the Church of Saint Agostino. Your final stop will be at the famous town of Pisa, which is also a UNESCO world heritage site. In the Piassa dei Miracoli the masterpieces in marble rise from the green lawn, including the famous Leaning Tower of Pisa, the magnificent Baptistery, the stunning Cathedral and the Monumental Graveyard Tuscany is a one-of-a-kind region of boundless natural and cultural beauty. This small, personalized tour is an authentically Tuscan experience.

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From Rome: Full-Day Trip to Tuscany with Wine Tasting

6. From Rome: Full-Day Trip to Tuscany with Wine Tasting

This tour has been designed to showcase the very best of Tuscany in just one-day and is perfect for travelers who only have a short amount of time. The day begins with departure from Rome at 6:45am on a fast speed train to Florence. Upon arrival in Florence, head to the meeting point sent to your email to meet your guide and set out on your sightseeing adventure. The first stop of the day is the historic city of Siena, which is bursting with rich architectural styles, best showcased at the cathedral and the old palace. After a brief guided walking tour of Siena, enjoy free time to explore on your own. Wander around the quaint streets of this magical town, have a traditional Italian lunch at one of the many cafés, or shop for handmade crafts and souvenirs. Continue the tour to the walled town of Monteriggioni next, which was the filming location of the blockbuster movie, Gladiator. Arrive at the UNESCO World Heritage Listed San Gimignano next, which is the most famous walled medieval town in Tuscany, and nicknamed the ‘Manhattan of Tuscany’ due to its many towers. Armed with tips and recommendations from your guide, head out on your own adventure in the town and visit the sights and attractions that interest you most. Don’t forget to stop by the store of the world-champion gelato maker, and treat yourself to a seriously sweet treat. Finally, ride through the rolling countryside of Chianti and soak up the charming scenic views on the way to an authentic Tuscan winery. Against the backdrop of luscious vineyards and olive groves, enjoy a spectacular wine and olive oil tasting session. At the end of a truly unforgettable day it’s time for the return journey to Rome, arriving at approximately 8pm.

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

7. 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.

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

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

Your day starts in the morning with a free tour of Pisa, where you will have time to admire the magnificent cathedral, the baptistery, the monumental cemetery and the famous Leaning Tower. Afterwards, you'll move on to a typical winery in the Chianti Hills on the slopes of San Gimignano. There you will enjoy a typical Tuscan lunch accompanied with a good local wine tasting. Following lunch you will 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. Your exciting day continues with a panoramic view of the true Chianti countryside before arriving in Siena, where if desired, your professional guide will let you discover 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, you can choose to have some free time to enjoy a cup of coffee or a pan forte (a typical local cake), and to go shopping in the typical local stores. Your return to Florence will have a magnificent sunset as a backdrop, which will make for a perfect ending to an unforgettable day spent in Tuscany.

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From Florence: Private Wine Tour with Dinner on an Estate

9. From Florence: Private Wine Tour with Dinner on an Estate

Meet your driver at your hotel and through this enchanting journey, you’ll discover one of the most suggestive areas of Tuscany, the Chianti Classico area. The first stop of the tour is at a family-run estate, located in the heart of the Florentine area of Chianti Classico. Here the wines are crafted with a bio-sustainable focus, always showing respect to the soil and the beautiful Tuscan countryside. Enjoy 4 fantastic wines and experience a true distilled of Tuscany. After that you will stop in the picturesque medieval village of Greve in Chianti, considered the gateway to the Chianti territory and famous for the main square, a treasure of art, history and flavors. It will be wonderful to snoop in the typical shops and experience the lively atmosphere of the village. Left Greve in Chianti, you will reach a second intimate and friendly winery where thanks to a private and exclusive tour of the estate, vineyards and wine cellars you will be introduced to the “wine world”. From the cultivation of the grapes to the tasting of the final product. And finally, enjoy the delicious Tuscan dinner with fine wines tasting. The last emotion of a full immersion into Chianti flavors, culture and beauties before returning to Florence. Please note that the itinerary of the visits may change.

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From Florence: Private Half-Day Chianti Tour & Wine Tasting

10. From Florence: Private Half-Day Chianti Tour & Wine Tasting

In the heart of Tuscany lies Chianti, a region of rolling hills and countryside that are unmatched in their beauty. Take part in a private tour of Chianti, which is made complete with a wine tasting that takes place in the cellars of a renowned winery. Adding to the luxurious nature of this tour and tasting, you determine when you want your tour to begin. When you are ready to depart your own private vehicle will come to your centrally-located Florence hotel. The car and your English-speaking driver are at your disposal for up to 4 hours. You will begin your experience with a drive through the Tuscan countryside to Chianti. En route you will see wooded areas, vineyards and olive groves, before a stop in a typical Medieval Chianti village. Make sure you bring a camera as the views are panoramic and unforgettable. Romanesque churches, charming farmhouses and villas and castles of rare beauty dot the landscape. Your wine tasting will take place in a historic wine estate and will focus on the famous and prestigious Chianti wines. You will learn about how Chianti was first made in the 13th-century as a white wine. Your tasting will also include some typically Tuscan snacks. A private car, tasting Chianti wine in a castle and touring the Tuscan countryside; does life get any better than this?

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Other Sightseeing Options in Chianti Hills

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What people are saying about Chianti Hills

Amazing trip that made our dreams come true.! We love so much the kindness and understanding of Sia who found us as we were lost and the trip would not have been. Sia was so knowledgeable and spoke both In English for us and Italian for others. We liked this trip as it was less people and that’s where we ended up making great friends. Recommend it highly!!

We really liked the tour. The guides Oscar has been wonderful, with very interesting and timely explanations. He has also given us good advice to move around the city and discover other points.

Highly recommend this for any tourist who wants to explore more of Tuscany but not sure on how to get around. You get a taste of everything in one day and definitely get your money's worth.

The second winery was really good. We visited in October so the grapes were already harvested and we didn’t get to see them but everything else was amazing!

everything left on time… ..well organized …… enough time to visit the places… ..comfortable trip… ..