Discover the enchanting world of Chianti as you embark on a full-day tour through Tuscany’s picturesque landscapes. Departing from Florence, you’ll explore charming medieval towns, indulge in wine tastings at renowned wineries, and gain insights into the region’s rich winemaking heritage. With a deluxe van at your disposal, this immersive experience promises to transport you to the heart of Tuscany’s captivating Chianti region. What hidden gems and delectable flavors await you on this unforgettable journey?
Key Points

- A full-day tour priced at $688.10 for up to 2 participants, exploring historic hill towns and visiting two acclaimed wineries in the Chianti region.
- The 8-hour tour includes free cancellation up to 2 days in advance and a pickup from Florence’s P. Signoria, 28.
- The itinerary features exploring the medieval streets of Montefioralle, a walk through the main square of Greve in Chianti, and a visit to a local winery for an optional 3-hour lunch.
- Highlights include scenic drives through Chianti’s picturesque landscapes, visits to two wineries for tastings of Chianti Classico, Supertuscan, Vinsanto, and extra virgin olive oil, and insights into the region’s winemaking history and traditions.
- The tour provides an immersive experience in the Chianti region’s winemaking heritage, with a focus on the rich traditions and techniques passed down through generations of vintners.
Tour Overview and Pricing
This Chianti Wine and Hill Towns Full-Day Tour provides a deluxe van experience that takes visitors on a scenic journey through Tuscany’s renowned wine region.
Priced at $688.10 for up to 2 participants, the 8-hour tour includes free cancellation up to 2 days in advance. Pickup is from Florence’s P. Signoria, 28.
The itinerary features exploring historic hill towns, visiting two acclaimed wineries for tastings, and an optional local lunch.
Travelers will enjoy the Chianti countryside’s rolling hills, vineyards, and olive groves. The tour highlights the region’s winemaking history and cultural insights, led by an expert guide fluent in multiple languages.
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Itinerary Details
The tour begins with a one-hour transfer from Florence to the picturesque village of Montefioralle.
A one-hour transfer from Florence takes visitors to the picturesque village of Montefioralle to begin the day’s tour.
Visitors will spend 20 minutes exploring the medieval streets and taking in the charming atmosphere.
Next, they’ll head to Greve in Chianti, where they’ll walk through the town’s main square for 20 minutes.
After, the group will drive to a local winery for an optional 3-hour lunch.
The tour then continues to a second winery, where guests will enjoy a 1.5-hour wine tasting, sampling Chianti Classico, Supertuscan, Vinsanto, and extra virgin olive oil.
The day concludes with a one-hour return transfer to Florence.
Tour Highlights

Travelers embark on a luxurious journey through Chianti’s picturesque landscapes, seeing the region’s winemaking heritage. The tour’s highlights include a scenic drive past rolling hills, vineyards, and olive groves. Visitors explore antique villages renowned for their beauty and wines, such as Montefioralle, Panzano, Castellina, and Greve. The tour also features visits to two acclaimed wineries, where guests savor Chianti Classico, Supertuscan, Vinsanto, and extra virgin olive oil.
| Winery 1 | Winery 2 |
| — | — |
| Chianti Classico | Supertuscan |
| Vinsanto | EVO Oil |
The tour provides invaluable insights into the history and traditions of Chianti winemaking, making it an immersive and unforgettable experience.
Cultural and Historical Insights
Though the Chianti region has long been celebrated for its exceptional wines, its winemaking history can be traced back to the 16th century.
In 1716, Chianti became the world’s first officially defined wine-producing area, solidifying its reputation as a premier destination for wine enthusiasts.
Visitors can learn about the rich traditions and techniques that have been passed down through generations of vintners.
From the renowned Chianti Classico to the bold Supertuscans, each varietal tells a story of the land and the people who’ve dedicated their lives to cultivating these celebrated wines.
More Great Tours NearbyLuxury Travel Experience
Embarking on this Chianti Wine and Hill Towns Tour, travelers enjoy a luxurious and captivating journey.
Whisked away in a deluxe van, they’ll experience the scenic splendor of Chianti’s rolling hills, vineyards, and olive groves. Comfort and convenience are the hallmarks of this tour, with an expert driver-escort providing seamless transportation and guiding them through the historic villages.
From the charming streets of Montefioralle to the renowned wineries, every aspect of the experience is meticulously curated to ensure a truly indulgent and memorable exploration of this renowned Italian wine region.
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Scenic Chianti Countryside
As the deluxe van winds its way through the rolling hills, travelers are treated to a mesmerizing display of Chianti’s breathtaking countryside.
The drive showcases a tapestry of verdant vineyards, olive groves, and medieval hilltop villages.
Some highlights include:
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Montefioralle, an ancient fortified town with its charming cobblestone streets and stunning vistas.
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Greve in Chianti, a picturesque market town known for its vibrant piazza and artisanal shops.
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Panzano, home to the iconic Cantinetta di Rignana winery, where visitors can savor the region’s renowned Chianti Classico.
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Castellina, a historic town with its impressive fortified walls and captivating architecture.
Winery Visits and Tastings
The tour’s winery visits and tastings allow guests to enjoy the celebrated viniculture of the Chianti region.
After exploring the charming hill towns, the group transfers to two renowned wineries. At the first, they savor Chianti Classico, Supertuscan, and Vinsanto wines.
The second winery showcases its expertise in crafting exceptional extra virgin olive oil. With ample time for leisurely tastings, guests discover the nuances of these renowned Tuscan products.
The experience provides an authentic opportunity to appreciate the region’s wine heritage and artisanal traditions firsthand.
Explore Charming Hill Towns
After exploring the scenic Chianti countryside, the tour takes visitors to the charming hill towns that dot the region.
These quaint villages offer a glimpse into the heart of Tuscan culture, with their winding cobblestone streets, historic architecture, and local artisans.
The quaint Tuscan hill towns reveal the region’s cultural heart through their winding cobblestone streets, historic architecture, and local artisans.
Highlights of the tour include:
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Wandering through the medieval hamlet of Montefioralle, known for its well-preserved stone houses and stunning views.
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Strolling through the lively market town of Greve in Chianti, the birthplace of the famous Chianti Classico wine.
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Discovering the charming villages of Panzano and Castellina, renowned for their artisanal crafts and traditional cuisine.
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Taking in the rich history and cultural heritage of these idyllic hill towns that have captivated visitors for centuries.
The Sum Up
Experience the enchanting Chianti Wine and Hill Towns Full-Day Tour and learn about Tuscany’s picturesque landscapes. Discover the region’s rich winemaking heritage, savor exceptional Chianti Classico and Supertuscan wines, and explore charming medieval towns. This deluxe van tour offers a luxurious and culturally immersive journey through the stunning Chianti countryside, delivering an unforgettable taste of Tuscany.
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