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Things to do in Chianti Hills

Our most recommended things to do in Chianti Hills

From Florence: Day Trip Pisa, Siena & San Gimignano w/Lunch

1. From Florence: Day Trip Pisa, Siena & San Gimignano w/Lunch

Experience the wonders of Tuscany on one memorable day. Leave Florence for a 12-hour excursion and see the beautiful landscapes, architecture, and artworks of the region. Treat yourself to some local cuisine, and choose a guided tour in your language to learn even more about the historic area. Begin with the visit to Piazza del Campo, where the Palio di Siena horse race is run, and Piazza del Duomo, where you will see the exterior of the magnificent cathedral. After some free time in Siena, have lunch in a typical Tuscan winery, then enjoy some local wine. Visit San Gimignano, a UNESCO medieval town, world-known for its Vernaccia di San Gimignano. The system of towers of San Gimignano tells the glories of the powerful families. Between saffron fields and typical indigenous vineyards, the city knows how to offer postcard views. Continue to Pisa and visit its stunning Piazza dei Miracoli. Admire the Baptistery, the cathedral of Santa Maria Assunta, and, of course, the famous Leaning Tower of Pisa.

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 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 Lunch at Chianti winery

3. From Florence: Tuscany Day Trip with Lunch at Chianti winery

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 Siena: Chianti and Castles Tour with Wine Tastings

4. 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.

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

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

Start in the morning with a tour of Pisa. Have time to admire the cathedral, the baptistery, the monumental cemetery, and the famous Leaning Tower. Then move on to a typical winery in the Chianti Hills on the slopes of San Gimignano. Enjoy a Tuscan lunch accompanied by a local wine tasting. Following lunch 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. Continue on with a panoramic view of the Chianti countryside before arriving in Siena, where if desired, your professional guide will take you to see 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, choose to have some free time to enjoy a cup of coffee or a panforte (a typical local cake), and to go shopping. Your return to Florence will have a gorgeous sunset in the backdrop, making for a perfect ending to an unforgettable day spent in Tuscany.

From Florence: Small Group Wine Tasting Tour to Tuscany

6. 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: Siena, San Gimignano & Monteriggioni Tour

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

Experience the charm of Tuscany on a day trip to Siena, San Gimignano, and Monteriggioni from Florence. Try a variety of Chianti wines paired with snacks and admire the picturesque Tuscan hills.  Cross the beautiful Chianti hills as you ride south from Florence in an air-conditioned GT bus. The first stop is at Monteriggioni, a medieval hilltop town that is famous for its intact medieval city walls. After some free time, head to the world famous Siena. Explore the Piazza del Campo, that is known for the Palio Horse Race and for its splendid examples of Gothic civic architecture. Have time to visit the magnificent Palazzo Pubblico.  Arrive in 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 lush landscape. Finally, 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 Half-Day Afternoon Tour

8. From Florence: Chianti Half-Day Afternoon Tour

Discover the Tuscan wine region of Chianti on a scenic guided tour by van from Florence. Visit a local wine estate, tasting its wines and local produce. Immerse yourself in the surrounding picturesque landscape, with a visit to a medieval village in the region. Visit a charming Chianti wine estate, enjoy a guided tour of its wine cellars, and gain an insight into the various stages of wine production. Afterward, enjoy some wine tastings. Visit a winery that not only offers a tasting that even true connoisseurs will enjoy with great pleasure, paired with some Tuscan samples, but you will also get to enjoy the wonderful surrounding landscape, immersed in an enchanting and welcoming atmosphere. Visit a real Medieval architecture village in Chianti hills, enjoy some free time to stroll out, and breathe in the local atmosphere. You'll also have the opportunity to buy Italian wine, Chianti Classico, olive oil, balsamic vinegar, cheese, and herbs to take home.

Florence: S. Gimignano, Siena, Chianti Lunch & Wine Tour

9. Florence: S. Gimignano, Siena, Chianti Lunch & Wine Tour

Embark on a scenic guided tour from Florence to the charming Tuscan towns of San Gimignano, Monteriggioni, and Siena. Stroll around the historic villages and enjoy a delicious Chianti Hills wine and balsamic vinegar tasting. Upgrade your experience with tickets to Siena Cathedral. Start at San Gimignano, the world-famous walled town located on a hilltop, which has remained intact through the centuries and is known for its tall towers, frescoes, and many other works of art. Take around 2 hours of free time to explore the city center. Visit the historical walled hamlet of Monteriggioni. Cross Chianti’s rolling hills to a cozy winery where you can relax and enjoy three wines and balsamic vinegar, followed by a Chianti-style three-course lunch. Enjoy a guided tour of Siena’s historic center (if selected in the option), starting with the 13th-century Basilica of San Domenico. Stroll along the narrow medieval streets of the city, flanked by splendid palaces and historic shops. Pass through the Piazza del Campo and visit the cathedral, if you select the option.  Take some free time in Siena before returning to Florence.

From Florence: Chianti Hills Full-Day Tour with Wine Tasting

10. From Florence: Chianti Hills Full-Day Tour with Wine Tasting

Embark on a guided day trip to Chianti from Florence and savor the fine notes of regional wines paired with authentic Tuscan products. Learn about the region from your guide and explore the town of Radda. Depart Florence for the enchanting area of Chianti, known for its highly appreciated wine. During the trip, your guide will explain the history of the region and its strong tradition of wine production. Take photos of the breathtaking panorama with rolling hills and vineyards. Stop in the picturesque town of Radda in Chianti and make your way to the wine cellar. Savor three locally produced wines paired with seasonal snacks to enhance the nuances of taste and smell. Then, enjoy free time to explore the quaint center of Radda. Continue to a farm nestled in the Chianti Hills and take a tour of the vineyards and the wine cellar. Listen to the owners as they explain how the grapes get to the bottle. Then, begin your second tasting of three local wines accompanied by tastings of beloved Tuscan products.

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What people are saying about Chianti Hills

Overall rating

4.5 / 5

based on 15,883 reviews

recommended to all girls who want to do a solo tour in tuscany. This tour was very interesting, comfortable and safe. The weather was perfect for take some shots and the wine tastings in the cellars created a film-like atmosphere. Thank you for this veeery on-a-budget experience

wine tasting with visit to a village in the countryside. Really appreciated the explanation of the lady in the first vineyard you can see that she loves her job. We bought a bottle as a souvenir

Lisa was exceptional in describing the Florentine culture and pairing the food tour to the cheeses and wines of the region. The tour was entertaining and well done. Good job!

I got really excited! It was a beautiful sunny day in Tuscany. Not only the leaning tower, there is so much to discover and I was very surprised by Saint Gimigagno!

Everything was perfect, really enjoyed the tour. Beautiful Sienna I hope to be able to visit it again