Chianti Hills
Transportation

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Our most recommended Chianti Hills Transportation

From Florence: Private Full-Day Jewels of Tuscany Tour

1. 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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Florence: Experience Siena, San Gimignano, and Chianti

2. Florence: Experience Siena, San Gimignano, and Chianti

Explore the beauty of Tuscany in this tour from Florence to Siena, Castello di Monteriggioni, Chianti, and San Gimignano. Visit medieval towns and villages, and drive through idyllic vineyards, with the option to stop at an organic farm and winery for lunch. Meet your friendly guide at your accommodation and drive in an air-conditioned minivan to see the distinguished medieval architecture in Siena, like the seashell-shaped Piazza del Campo and Siena Cathedral before enjoying a scenic drive to Castello di Monteriggioni. Enjoy the small, fortified village and take a short stroll after lunch at one of the local restaurants. Travel along the Chianti wine road which is rich with castles and villages with a stop to admire a small medieval village surrounded by endless vineyards. Experience a unique dining setting while taking in an amazing Tuscan panorama with lunch at an organic farm in Castellina, with the lunch option. Journey to historic center of the picturesque medieval town of San Gimignano and see its ancient towers.

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From Florence: Tuscany Day Trip with a Private Chauffeur

4. From Florence: Tuscany Day Trip with a Private Chauffeur

Spend a day exploring the Tuscan countryside on a chauffeur-driven tour. Immerse yourself in Tuscan culture as you visit Siena's main attractions, explore an ancient hilltop town and discover one of Italy's most beloved wine regions. Your day begins with a hotel pickup to take you to the first stop on your sightseeing excursion, Siena. This historical city is a UNESCO World Heritage Site and famous for its Palio, the bareback horse race that takes around its main piazza. Visit the three must-see attractions in Siena, the Piazza del Campo, Palazzo Pubblico, and the iconic Cathedral, one of the few examples of Italian Gothic architecture. Head back to your car and continue your tour of Tuscany with a drive to the walled hilltop town of San Gimignano. Dubbed the Town of Fine Towers, San is renowned for preserving more than a dozen medieval towers. Wander through this ancient city, explore the alleys and see the Piazza del Duomo and the seven towers that surround this town square. End your day of sightseeing with a visit to the Chianti wine region. Marvel at the unforgettable landscapes with its rolling hills, vineyards, and olive groves.

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From Florence: Siena, San Gimignano & Chianti Private Tour

5. From Florence: Siena, San Gimignano & Chianti Private Tour

Amongst the vineyards and olive groves of Chianti, lie medieval towns and UNESCO heritage sites. Explore them all on a private, 8-hour tour of the Chianti countryside, Siena and San Gimignano. A truly private tour, you will begin your day with complimentary pick-up at your Florence hotel by chauffeured private vehicle. Your English-speaking driver is at your disposal for a maximum of 8 hours. Your first stop will be in Siena, a medieval town. Here you will meet with your private tour guide, who is at your disposal for a maximum of 2 hours. Your guide will take you through the historic city center, where you may admire the splendid palaces and other points of interest. Your tour of Siena will conclude in the Piazza del Campo, one of the most beautiful piazzas in the world. Here, you will find the Palazzo del Comune and have some free time to enjoy lunch. The journey to your next stop, San Gimignano, will take you through Chianti territory. Along the road you will find panoramic vistas, as well as lush vineyards and olive groves. Along the way to San Gimignano you may wish to stop and admire the fortified hamlet of Monteriggioni. This hamlet is a small jewel built in the 13th-century and still embraced by ancient walls. San Gimignano you will find is a UNESCO designated world heritage site. Here you will be given free time to take in the historically interesting medieval town planning, as well as the numerous towers. You will soon find out why this place is called the “Manhattan of the Middle Ages”. Touring this extraordinary region of Italy is a wonderful experience and the fact that this tour is entirely private makes it even more special.

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From Florence: Private Wine Tour with Dinner on an Estate

6. 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

7. 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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San Gimignano: Private Chianti Hills Tuk-Tuk Tour

8. San Gimignano: Private Chianti Hills Tuk-Tuk Tour

You'll depart from the headquarters located in Poggibonsi at 10:45AM, where your wonderful guide will welcome you. From there you will venture then through the panoramic roads of Tuscany and the Chianti hills where you are bound to fall in love with the fields of vines, cypresses, and Tuscan rural houses. Don't forget to bring your camera, as there will be plenty of photo opportunities to capture the eagerly awaited moment and freeze it in time. Your next stop will be to a local winery where the kind owners will take you around their property before serving a wonderful and authentic Tuscan meal complete with a wine and extra virgin olive oil tasting. Following lunch you will hit the rad once again to travel through the iconic Ape Calessino to enjoy the last part of this scenic drive. You will later arrive back to the office at approximately 3:45PM, which will mark the end of your tour.

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From Livorno: Siena and Chianti Day Trip with Wine Tasting

9. From Livorno: Siena and Chianti Day Trip with Wine Tasting

Immerse in a day of exploring rolling hills, medieval art, grapevines, and Tuscan flavors. Visit the main square and Gothic cathedral in Siena. Explore the breathtaking landscapes of Chianti. Visit a winery and have a tasting of different wines. Start your private day tour from the port of Livorno. Discover Siena's artistic and cultural heritage. Learn about the annual Palio horse race held there that attracts huge crowds. This medieval city is also home to architectural masterpieces including the Palazzo Pubblico, located in Piazza del Campo, with its Torre del Mangia. Explore the stunning Siena Cathedral, one of the few remaining examples of Italian Gothic architecture. Then, travel through the stunning hills of Chianti, a region famous for its scenery and vineyards. Arrive at a local winery to taste some Chianti and learn about how their grapes are produced. After a guided tour, indulge in a rich sampling of wines and delicious local produce, followed by the opportunity to purchase these local products. After a full day in Tuscany, be taken back to the port by your driver, in time to board your ship.

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From Florence: Chianti Rufina Private Tour And Food Tasting

10. From Florence: Chianti Rufina Private Tour And Food Tasting

Discover Chianti Rufina, the smallest Chianti sub-region and one of the most important wine-producing areas in Tuscany. Visit two boutique wineries, take part in olive oil and wine tastings, and enjoy a lunch with km 0 products as you learn about this historical wine area. The first winery you will visit has been owned by the Gondi family since 1592. It features 315 hectares of which 19 are vineyards, 32 are olive groves, and the rest are cereals and woods. The second winery is located on top of the hill of Montefiesole at 450 meters above sea level, just 18 km from Florence. It is a typical Tuscan family business whose philosophy is to harmonize with nature all its endeavors. During the tour, enjoy a typical lunch on the terrace of a farm restaurant overlooking a landscape full of charm. Wine has been produced in the Chianti Rufina region since Etruscan times. The first historical evidence of wine production in the area dates back to the early 15th century. The famous Medici family identified a particular aptitude for the production of great wines here. In 1716, Cosimo III de' Medici included Chianti Rufina in the “Bando dei Vini,” the first world law regulating wine.

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Other Sightseeing Options in Chianti Hills

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What people are saying about Chianti Hills

Fantastic experience !! Alessandro provided solid communication before, during & after our tour. He was on time, provided great information during the different visits and was very attentive to all our questions. As someone that has completed many tours like this, I particularly appreciated the patience with the family (when you have kids!!!) as well as the good driving. Highly recommended !!!

The chauffeur enthusiastically introduces each Chianti location and attraction, in addition to the beautiful Montecchio winery and the delicious red wines such as Chianti Classico. The driver also took us on a tour of the village of Chianti. Nice Trip!

A very interesting route and the guide very friendly and interested in telling us

Excellent day out.

Driver/Guide was fantastic As were the places we visited & the people we meet

Marco did a great job and provided a lot of Information that was very useful