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Chianti Hills

Tours

Our most recommended Chianti Hills Tours

Florence: Chianti Wineries Tour with Food and Wine Tasting

1. 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.

From Florence: Tuscany Day Trip with Optional Lunch and Wine

2. 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: Small Group Wine Tasting Tour to Tuscany

3. 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: Tuscany Wine & Food Tour with Guide

4. 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.

From Siena: Dinner in the Chianti Vineyards

5. From Siena: Dinner in the Chianti Vineyards

Discover the history, landscapes, wines, and culinary traditions of Chianti on this day trip from Siena. Travel in a comfortable and climate-controlled vehicle to a quaint farm in the hills. Engage your senses as you try a range of wines and savor a gourmet dinner.  Enjoy the convenience of being picked up from a centrally-located meeting point in Siena. Admire the Tuscan countryside as you travel to a farm tucked away in between rows of vineyards where grapes ripen in the Italian sun.  Pick up a wine glass to carry with you on your visit to the farm's winery. Sample a variety of delicious wines as you walk along a charming wine route. Visit the estate’s historic chapel before finally heading to your candle-lit dinner under the stars.  Listen to harmonious background music and lookout at the vineyards as you indulge in a farm-fresh gastronomic experience made from traditional recipes. Taste pappa al pomodoro or ribollita ( both are variations of Tuscan bread soup) and barbecued meat served with seasonal vegetables.  Let yourself get carried away by the warmth and fragrances of the barbecue and the perfumes of the grapevines, which enhance the dining experience. After dinner be escorted back to Siena where the tour will finish.

From Siena: Chianti and Castles Tour with Wine Tastings

6. From Siena: Chianti and Castles Tour with Wine Tastings

Immerse yourself in picturesque Tuscan scenery on a sightseeing day trip from Siena to the region of Chianti. Visit the Castellina in Chianti before partaking in a wine tasting experience at a wine estate.   Board a spacious and climate controlled van in a centrally-located meeting point in Siena. Admire the Italian countryside on the ride as you pass thorugh pristine landscapes that have been cradling the Chianti vineyards for centuries. Discover a harmony of colors that can only be found in the hills of this region. Delight your senses as you dive into the sounds, scents, and flavors of this land will capture your senses through this unique experience.  Visit ancient churches, medieval castles, and small villages where the rhythm of life remains unaltered over time. Continues to a charming wine estate.  Indulge in a wine tasting paired with typical Tuscan food. View the beautiful ruby-red color and the characteristic bouquet with scents of violet are the special to Chianti wine. Savor this blend of Sangiovese, Canaiolo, Merlot and Cabernet Sauvignon grapes. Later, move on to another winery in the middle of the Chianti Classico area, where you’ll have a second optional wine tasting alongside an extra virgin olive oil tasting. The tour will end with a return to Siena.

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 San Gimignano: Chianti Half-Day Vespa Tour with Lunch

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

Start your experience in the morning 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 in the early afternoon.

From Florence: Chianti Wine Tasting at Sunset Day Trip

9. From Florence: Chianti Wine Tasting at Sunset Day Trip

Experience for yourself what makes Tuscany so beautiful as you explore the stunning landscapes of the Chianti Hills, a mountainous area of Tuscany in the provinces of Florence, Siena and Arezzo. Travel from Florence aboard a comfortable and climate-controlled vehicle.  Choose Enjoy an afternoon tour in a comfortable car or minivan, traveling through the region's. Be captivated by views of vineyards, cypress trees and hilltop villages, with a glorious view around every bend.  Explore a wine estate and visit the cantine (cellars). Indulge in a tasting experience of delicious local wines and enjoy a typical Italian appetizer (cheese with jam and bruschetta).  Enhance your experience by selecting the option that includes dinner at an open-air restaurant in the countryside to taste some Tuscan specialties and drink good Chianti wine. Return to your meeting point in Florence at the end of your tour. 

Tuscany by Vespa Full-Day Tour to Chianti Wine Region

10. Tuscany by Vespa Full-Day Tour to Chianti Wine Region

Take a ride on the iconic Vespa, through the lush countryside of Tuscany. We will pick you up with one of our comfortable, air-conditioned mini-vans and we'll take you to the countryside, away from the busy city. In just 15 minutes you'll be at the doors of Chianti countryside. Then you will receive an orientation on how to use the Vespa safely, before we head out for our engaging and enjoyable ride. Driving at a relaxed pace along quiet and scenic country roads, you will be offered beautiful views of the rolling hillsides. We will visit different medieval villages in the heart of Tuscany and enjoy the most incredible landscapes. Next, we will stop at a 17th-century villa for a typical Tuscan meal and a guided tour of the vineyards and cellars, with wine tasting and olive oil tasting.

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Frequently asked questions about Chianti Hills Tours

What are other things to do than Chianti Hills Tours that are worth visiting in Tuscany?

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Other Sightseeing Options in Chianti Hills

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What people are saying about Chianti Hills

Overall rating

4.9 / 5

based on 2,770 reviews

This was the perfect day trip to see Tuscany in a day (if that’s all the time you have). Our guide Manolo was amazing and so informative. He gave good recommendations and some history lessons throughout the day. He was always checking in with us and made sure we were having a good time! Thank you to him! If you can, opt for the farm lunch, it was lovely and a good opportunity to taste some wines from the region. Although it is a long day, you get plenty time to rest on the bus in between places. I would highly recommend this to anyone.

Sara our guide and Enrico our driver gave us a really good day out, very friendly, well organised and caring. The tour around Sienna was excellent with expert commentary from the local guide, with fascinating details of the Palio. The lunch near San Giminiano was excellent and the town very atmospheric. Pisa and the Leaning Tower finished the day well. Just the right amount and blend of commentary from Sara and very friendly manner, and faultless English. Chris & Clare from Prestwood, Bucks, England.

Amezing experience. Well organized. Food could have been better for vegetarians. Elizabeth you are an amazing tour guide.

Fantastic experience - Stefano was an amazing guide who made every effort to have our trip be fun, easy and informative.

Really enjoyable and experience and well organised. Would recommend