Chianti Hills

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Chianti Hills: Our most recommended tours and activities

From Florence: Tuscany Day Trip with Optional Lunch and Wine

1. 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 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.

From Florence: Tuscany Wine Tasting Full-Day Trip

3. 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.

From Florence: Siena, San Gimignano & Monteriggioni Tour

4. 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.

From Florence: Chianti Wine Tour with Tasting

5. 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!

Wine Tasting and Dinner in the Vineyards of Chianti

6. 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.

Florence: Siena, San Gimignano, & Monteriggioni Day Tour

7. Florence: Siena, San Gimignano, & Monteriggioni Day Tour

Explore the heart of beautiful Tuscany on a full-day tour of the towns of San Gimignano and Siena, then discover the bucolic wine region of Chianti. Depart from Florence by an air-conditioned bus to your first stop, the UNESCO World Heritage Site of San Gimignano. Discover one of the most splendid examples of an Italian medieval town. Distinguished by its famous towering skyline, San Gimignano stands along the Via Francigena on the hills of the Upper Val D’Elsa. Get acquainted with the Tuscan environment with the town’s Vernaccia di San Gimignano wine, saffron, and Santa Fina pottery. Enjoy some free time to stroll through the town on your own and see its beautiful squares, architecture, churches, and side streets. Afterward, head out to a unique location in the Chianti countryside to enjoy a wine tasting. Once you hop off the bus, be guided around a splendid winery. Get introduced to the estate's fascinating history and background. Head inside the cellars to learn the secrets of Chianti winemaking together with the local host. Then enjoy a delicious wine tasting of Chianti Classico. Continue to Siena for a guided tour of its enchanting architectural styles, including the Cathedral (exterior only) and Palazzo Comunale (Municipal Building, exterior only) in Piazza del Campo. The famous shell-shaped square provides the stage for the thrilling Palio horse race, run twice every summer.

From Siena: Dinner in the Chianti Vineyards

8. 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.

Siena, San Gimignano and Chianti with Wine Tasting and Lunch

9. Siena, San Gimignano and Chianti with Wine Tasting and Lunch

Along the way that will lead you to Siena, stop at San Gimignano, a small and world famous walled town located on a hilltop, which remained intact through the centuries, renowned for its tall towers, wonderful frescoes and many other valuable works of art: here you will be led until the heart of the historical center, where you have free time at disposal for its fascinating discovery. Following San Gimignano,  stop at the charming historical hamlet of Monteriggioni, an amazing medieval village enclosed by its famous walls, which have remained standing to this day. Enjoy some free time to visit this village. Then, crossing the gently Chianti rolling hills, arrive at a small and typical winery where you will taste 4 fantastic wines and sample balsamic vinegar and locally produced delicacies. Upon arrival in Siena, after free time for lunch, meet your local guide. Take a comprehensive guided tour of the historic center, starting from its most beautiful square, Piazza del Campo. Walk along the narrow medieval streets of the city, flanked by splendid palaces and historic shops, until you reach the Museum and Oratory of a Contrada (when open), where you can experience the atmosphere of the authentic and most intimate soul of the town. The “Contrade” (districts into which the city is divided) are the real core of local social life, where inhabitants of each district compete with each other, as they devote themselves to the preparation of the famous Palio horse-race. The Museum of a ”Contrada”, as well as its Oratory, is therefore the heart of the district. It is an intimate and secret place containing historical documents and wonderful relics of the famous Palio, as well as magnificent works of art which are normally not disclosed to the public. If you wish, your tour can include a guided visit inside the famous Siena Cathedral, built in the 12th century, to discover the beauty of its treasures and works of art.

From Siena: Chianti and Castles Tour with Wine Tastings

10. 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.

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

Great day with free lunch at the middle of Tuscany farm with excelent appetizer and quality of food. Great italian product and a good tourist guide. This is our 4rrh time for get your guide and its always worth. But not good for elderly person because of time. The trip was confortable and with nice abd goid driver. 12 hrs exsact. We arrive earlier but its fine. The meeting place was perfect for us, because we need to catch up the train after wards. Am sure that we will do it again on get tour guide. Thanks!

First of all Camilla, was the best. She did a wonderful job explaining each location we visited. The view from the winery/farm was breathtaking. The wines we tasted were excellent and the food was delicious. It was all very well organized . Fellow tourist all followed timing guidelines so that made for a better tour. In my opinion Pisa could have been left off this trip for another winery visit.

Great activity that allows you to get to know 4 places in the same day. San Gimigniano is magical and the wine tasting is a lot of fun. I highly recommend it.

Daniel was an excellent guide, we enjoyed every stop of the tour and look forward to recommending it to our friends.

Constantino is very good and interested in everybody