Discover the Charm of Chianti on a Private Luxury Tour from Florence

If wandering through Tuscany’s rolling hills, sipping world-famous Chianti wines, and exploring quaint medieval villages sounds appealing, this private tour from Florence might just be your perfect day out. Costing around $737.53 per group (up to two people), it offers a full-day journey—roughly 8 hours—in a comfortable, luxury minivan with your own driver and guide. You’ll visit iconic spots like Greve in Chianti, Castello di Montefioralle, and enjoy tastings at boutique wineries like Brogioni SAS and Casa Emma.
What we love about this experience is how flexible it is—your driver can suggest hidden gems and local favorites, making it feel like a day spent with a knowledgeable friend. Plus, the opportunity to walk through a medieval village, sample organic wines, and enjoy authentic Tuscan snacks makes it a well-rounded, immersive experience.
Of course, there’s one consideration: additional costs for tastings and meals can add up, so if you’re on a tight budget, planning for extra expenses is wise. This tour is best suited for travelers who want a personalized, in-depth look at Chianti’s wines and villages without the hassle of self-driving or group tours with too many people. It’s ideal if you’re craving authenticity, comfort, and expert guidance.
Key Points
- Customizable itinerary: you can choose to visit specific villages and wineries or follow the driver’s recommendations.
- Expert guide/driver: knowledgeable about Tuscany’s traditions, wines, and local stories.
- Authentic experiences: tasting at boutique wineries, exploring medieval villages, sampling local foods.
- Comfort and privacy: private luxury minivan for up to two people, Wi-Fi and bottled water included.
- Flexible timing: full day with stops designed around your interests.
- Additional costs: wine tastings and meals are extra, so budget accordingly.
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An Authentic Taste of Tuscany: A Deep Dive into the Chianti Private Tour

When we consider a day trip from Florence into the heart of Chianti, the goal is to blend scenic beauty, cultural richness, and delicious wine into a seamless experience. This private tour delivers on that promise, offering an intimate look at Tuscany’s most renowned wine region in comfort.
What’s Included and How It Works
Starting at 9:30 am, your driver picks you up at your hotel, ensuring a stress-free start. The tour is entirely private, meaning only your group participates, which makes for a more relaxed, flexible day. A key feature is the luxury minivan—roomy, air-conditioned, with optional Wi-Fi—perfect for enjoying the views and sharing stories with your driver.
Throughout the day, you’ll visit a series of charming spots, each chosen to highlight different aspects of Tuscan life. You’ll get personalized attention and the chance to ask questions, making it more engaging than a typical group bus tour.
Exploring Greve in Chianti and Castello di Montefioralle
Your first stop is Greve in Chianti, a pretty town known for its famous navigator Giovanni da Verrazzano and its historic butcher shop. It’s the ideal place for a quick stroll, some photos, and tasting local cold cuts and cheeses—a favorite among past travelers who enjoyed the authentic flavor and small-town charm. One reviewer mentions, “a nice stop in the small town of Greve in Chianti, home of the Falorni butcher shop where we tasted fabulous local cold cuts,” highlighting how this spot offers a genuine taste of Tuscany.
Next, the tour takes you to Castello di Montefioralle, a medieval village with just 79 inhabitants, considered “one of the most beautiful villages in Italy” by many. Expect narrow stone streets, panoramic views, and plenty of photo opportunities. As one traveler notes, “it’s truly a pearl of Tuscany,” and visitors often enjoy a leisurely stroll, soaking in the untouched, historic atmosphere.
Wine Tastings at Boutique Wineries
The heart of the experience is the wine tastings. The first is at Brogioni SAS, a small, organically certified producer where everything is done by hand—from grape harvest to bottling. For wine lovers, this is a highlight, as it offers a chance to taste high-quality, small-batch Chianti Classico in an intimate setting. “The wines here are completely organic and handcrafted,” according to reviews, making it a memorable stop for those interested in artisan wines.
Following this, you’ll visit Sant’Appiano, a family-run farm that combines tradition with modern techniques. This estate produces more than just wine—olive oil, cheeses, and grappa are also on offer, providing a true taste of Tuscan craftsmanship. Visitors appreciate the warm, personal atmosphere, with one reviewer noting the familiar character of the estate.
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- Luxury Chauffeur Service THE MALL from Florence to Reggello
- Vip early Skip-the-Line Uffizi Gallery
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A Personal Touch in Tuscan Cuisine
The tour includes an option for a lunch or wine tasting experience at Casa Emma, where you can enjoy local wines alongside Tuscan snacks—think cheeses, salami, and bread. While this is an additional expense (roughly $40–$60 per person), many find the quality and authenticity well worth it. Reviewers consistently praise the delicious food and well-chosen wines, making it a perfect way to relax and refuel after a morning of sightseeing.
Scenic Drive and Panoramic Views
One of the joys of this tour is the drive along Strada Statale 222 Chiantigiana, where the scenery unfolds in sweeping vistas of vineyards, olive groves, and rolling hills. It’s the kind of landscape that makes you want to reach for your camera, and many travelers comment on how “beautiful and peaceful” the scenery is—ideal for a lazy, scenic drive.
Why This Tour Stands Out

What makes this experience truly shine is the balance of freedom and expertise. Your driver isn’t just a chauffeur but a storyteller, offering insights into Tuscan culture, wine production, and local traditions. Several reviews highlight guides like Simone and Luciano, who are both praised for their knowledge, friendliness, and helpfulness.
On top of that, the customizable itinerary means you can prioritize your interests—whether it’s visiting a particular village, tasting specific wines, or exploring a hidden corner of Chianti. This flexibility, combined with the luxury transportation, makes for a comfortable, personalized experience that’s far superior to crowded group tours.
Value for the Money
Considering the full-day itinerary, private transportation, and expert guidance, the price of just over $700 for two people offers good value—especially if you value comfort, flexibility, and authenticity. Keep in mind that wine tastings and meals are extra, but these often include high-quality products and can be tailored to suit your taste and budget.
Who Would Love This Tour
This experience suits couples, friends, or small groups who want an intimate, thoughtful day in Chianti. It’s perfect for those who appreciate local wines, scenic drives, and medieval villages but don’t want to be part of a large, impersonal bus tour. If you’re food and wine enthusiasts eager to learn about artisan producers, or simply want a comfortable, flexible way to see Tuscany’s countryside, this tour checks all the boxes.
FAQ

Is this tour suitable for solo travelers?
This particular experience is designed for up to two people, so it’s best for couples or two friends. Solo travelers would likely need to book the full private tour for themselves, which is available but at a higher rate.
What’s included in the price?
The cost covers hotel pickup and drop-off, the private luxury minivan, an English-speaking driver, bottled water, and Wi-Fi on request. Wineries, tastings, and meals are additional expenses.
Can I customize the itinerary?
Yes, you can choose to visit specific villages or wineries, or rely on your driver’s suggestions for the best experiences, making it a personalized day.
How long are the stops at each location?
Stops vary from about 1 to 2 hours—enough time to enjoy a walk, take photos, and sample products. The largest tasting stops are at Brogioni SAS and Casa Emma, each lasting about 2 hours.
What is the meeting point?
The tour begins at 9:30 am, with hotel pickup arranged. Specific pickup details will be confirmed upon booking.
Are wine tastings included?
Not automatically. Tastings at small producers are not included in the base price but typically cost $15–$25 per person. Some tastings might be free if you purchase wine.
Is this tour suitable for children?
The minimum drinking age is 18, so it’s best suited for adults or older teens interested in wine and culture.
What should I wear or bring?
Comfortable shoes for walking in villages, sunglasses, and sun protection are recommended. You’ll want your camera to capture the stunning scenery!
Final Thoughts

This private Chianti tour offers a personalized, comfortable way to explore Tuscany’s iconic wine country. The expertise of your guides, combined with the flexibility to choose your stops and the opportunity to visit authentic villages and boutique wineries, makes this a standout experience. It’s ideal for travelers who value quality over quantity, seeking a deep and genuine look at what makes Chianti special.
While the added costs for tastings and meals mean planning ahead is wise, many past travelers found the delicious wines, beautiful scenery, and warm hospitality well worth the extra expense. The experience’s flexibility makes it perfect for those who want to craft their ideal day in Tuscany, away from the crowds and with a true local touch.
If you’re looking for a luxurious, intimate way to learn about Chianti’s landscape, wines, and villages, this tour will deliver a memorable day full of flavor, history, and scenic beauty.
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