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Experience a private full-day Chianti wine tour from Florence featuring visits to medieval towns, exclusive wine tastings, and personalized service with a knowledgeable guide.

This private Chianti wine tour offers an exceptional way to explore the Tuscan countryside, departing from Florence for a full day of wine tasting, sightseeing, and culture. Priced at $380.29 per person, it provides a tailored experience designed for wine lovers seeking a personalized journey through some of Italy’s most iconic villages and vineyards. The tour lasts approximately 8 hours, making it a great choice for those wanting an immersive yet manageable day trip.
With hotel pickup and drop-off included, travelers can relax and enjoy the scenic drives without hassle. The use of a luxurious Mercedes Vclass minivan ensures comfort, while the driver-guide enriches the experience with insights into the region’s history and traditions. This tour is ideal for small groups looking for a flexible, private adventure that balances wine tasting with exploring charming towns.
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The tour begins at 9:00 am, with a convenient hotel pickup in Florence. From there, the driver leads travelers through scenic small country roads toward Montefioralle, a stunning medieval village perched on a hill. This picturesque spot offers a brief walk through its historic streets, giving a taste of authentic Tuscany. The peaceful atmosphere and quaint architecture provide perfect photo opportunities.
After this gentle introduction, the journey continues downhill to Greve in Chianti, often called the region’s “capital of Chianti wine.” The town’s central square invites visitors to relax among small shops and perhaps explore the Wine Museum, which offers insights into local wine traditions. The town’s lively yet cozy vibe makes it an ideal first stop for soaking up the region’s ambiance.

Next, the tour moves to Panzano, a charming town known for its food and wine scene. Here, a local winery hosts the group for a guided visit of the cellars and vineyards. Visitors get an inside look at how authentic Chianti wines are made and stored, with the opportunity to taste 3 different types of wine, alongside grappa and Vin Santo—a famous Tuscan dessert wine.
The winery experience typically includes a guided cellar tour, where the owner shares stories about the winemaking process. There’s also a chance to enjoy lunch at the winery, which can be included or replaced with a recommended trattoria, depending on preferences. This flexibility ensures that the visit aligns with individual tastes and schedules.

Following the winery visit, the tour proceeds to Castellina, a beautiful town characterized by narrow streets and historic charm. Here, travelers have time for a stroll through the town’s authentic wine shops, offering a chance to purchase local wines or simply enjoy the inviting atmosphere. The small-town ambiance and scenic vistas make Castellina a highlight of the day.
This stop allows guests to compare different wine styles at local shops and soak up the lively, authentic Tuscany atmosphere. The visit to Castellina emphasizes the region’s boutique wine culture, distinct from larger wineries, offering a more intimate tasting experience.

The last stop of the day is another boutique winery, where visitors observe different cellar styles and taste another selection of wines. This final tasting provides an excellent opportunity to compare wine profiles, enhancing understanding of regional variances. The guide explains the nuances of each wine, making this a valuable educational experience.
Afterward, the driver heads back toward Florence, usually arriving in the late afternoon. The journey concludes with drop-off at the original hotel, leaving guests with full bellies, happy hearts, and plenty of memories of the Tuscan countryside.
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One of the standout features of this tour is its private format. Only your group participates, allowing for a customized pace and the flexibility to spend more or less time at each stop. The driver-guide like Massimo (mentioned in reviews) adds personal touches, sharing insights about the area, culture, and winemaking, making the experience both educational and engaging.
The moderate physical activity involved—mainly walking through small towns and cellar visits—means it’s suitable for most people with average fitness. The tour’s flexibility in dining options also caters to different preferences, whether you want a sit-down wine pairing or a quick snack at a winery.

The tour departs from Florence at 9:00 am and includes hotel pickup and drop-off, making logistics seamless. The use of a luxury Mercedes Vclass minivan ensures comfort during the scenic drives. The driver/guide is responsible for navigation, narration, and making sure the group gets the most out of each visit.
The price of $380.29 per person covers transportation, fuel, and guiding services. However, wine tasting fees and lunch costs are not included, giving guests the flexibility to choose their preferred dining experience. Booking is recommended about two months in advance, as the tour is popular and booked well ahead.

Unlike larger group tours, this private option offers a more intimate look at the Chianti region with personalized attention. The emphasis on small wineries and medieval towns creates a more authentic Tuscan experience. The reviews praise the knowledgeable guides, especially for their ability to tailor the day to individual interests, and highlight the delicious wines and local food.
While the tour does not include the tasting fees or meals in the base price, the flexibility allows guests to customize their day, whether they prefer a leisurely pace or more wine tasting. It is well-suited for those who want a personalized and comprehensive Chianti experience in a single full day.
This private Chianti wine tour from Florence offers a balanced mix of historical towns, scenic drives, and authentic wine tastings, all led by a knowledgeable guide. The personalized service and flexibility make it a standout choice for those seeking an immersive day in Tuscany’s wine country.
While it does not include tasting fees or meals, the quality of visits to boutique wineries and the opportunity to explore medieval villages make it a valuable experience. The consistent high ratings reflect the care taken by guides like Massimo to provide a memorable, informative adventure tailored to wine lovers.
Ideal for small groups or couples, this tour combines comfort, culture, and wine in a way that truly captures the spirit of Tuscany. Expect beautiful scenery, delicious wines, and charming towns—all within a well-organized, private itinerary designed to give you a taste of the region’s best.
“Massimo was an excellent tour guide!! He tailored our experience to what we wanted , found nice wineries for us to visit, and took us to some neat…”
What is included in the tour price?
Transportation on a luxury Mercedes Vclass minivan, fuel surcharge, and a driver/guide are included. Wine tasting fees and lunch are not included.
How long does the tour last?
The tour lasts approximately 8 hours, starting at 9:00 am and ending in the late afternoon.
Can I customize the stops or tastings?
As a private tour, the experience can be tailored to your interests, with flexibility at each stop.
What towns are visited during the tour?
Stops include Montefioralle, Greve in Chianti, Panzano, and Castellina.
Is hotel pickup available?
Yes, hotel pickup and drop-off in Florence are included in the tour.
Are lunch and wine tastings included?
No, these are not included in the base price, allowing you to choose your preferred dining and tasting experiences.
What is the booking process?
It is recommended to book around 64 days in advance, as the tour is quite popular and fills quickly.
Is the tour suitable for all physical fitness levels?
Yes, the tour is suitable for those with moderate physical fitness, involving some walking in towns and winery visits.
Who provides the tour?
The experience is operated by Tuscany In Tour, known for their personalized Tuscan excursions.
Can I cancel the tour if my plans change?
Yes, free cancellation is available up to 24 hours in advance, ensuring flexibility for your plans.