Florence: Tuscany Chianti Winery Private Day-Trip with Lunch

Key Points

• Private 6-hour Tuscany trip starting from Florence, perfect for wine lovers and history enthusiasts
• Visits to Greve in Chianti and Montefioralle, featuring charming, well-preserved medieval villages
• Guided tour of a family-run estate, exploring medieval cellars and learning about olive oil production
• Tasting session with 3 top Chianti wines paired with a traditional Tuscan lunch made with organic, estate-grown ingredients
• Scenic drive along the ancient Roman road Cassia Vetus offering breathtaking views of vineyards and olive groves
• Flexible booking options with free cancellation up to 24 hours in advance

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Scenic Drive into the Heart of Chianti along the Roman Road Cassia Vetus

This tour begins in Piazza dei Cavalleggeri in Florence, where an English-speaking driver collects you for a scenic 60-minute drive into the Chianti region. The route traces the ancient Roman road Cassia Vetus, surrounded by rolling hills, vineyards, and olive groves that create a quintessential Tuscan landscape. This drive is notable for its panoramic vistas, which set a perfect tone for the day ahead.

As you travel, you’ll enjoy views that capture the essence of Tuscany’s countryside. The vehicle used is generally comfortable and suitable for small or private groups, making the experience intimate and relaxed. This initial segment prepares you for the charm and history that each stop in the Chianti area offers.

Photo Stop at Piazzale Michelangelo with Stunning City Views

Along the route, there’s a brief 10-minute stop at Piazzale Michelangelo. This famous viewpoint provides a sweeping look over Florence’s skyline, including the Duomo, Palazzo Vecchio, and Ponte Vecchio. It’s a perfect spot to snap photos before heading further into the countryside.

This stop offers a chance to appreciate Florence from above and get a sense of the city’s relationship with the surrounding Tuscany hills. While brief, it helps travelers transition from the bustling city to the tranquil rural scenery of Chianti.

Exploring Greve in Chianti, a Medieval Hilltop Village

Your first major stop is in Greve in Chianti, a lively village known as the birthplace of Giovanni da Verrazzano. You’ll have about 45 minutes to walk through its narrow alleys, browse local shops, and enjoy the vibrant atmosphere.

Greve’s main square features a charming open-air market, and the streets are lined with traditional stone buildings. This village preserves its medieval character, offering a glimpse into Tuscany’s history. Visitors often appreciate the opportunity to explore at their own pace, perhaps stopping for a coffee or local specialties.

Discovering Montefioralle, a Well-Preserved Medieval Hamlet

Next, a short 10-minute drive takes you to Montefioralle, a 12th-century stone village that has maintained its authenticity over the centuries. You’ll have about 45 minutes to stroll its narrow streets and enjoy the panoramic views over the Chianti hills.

Montefioralle is famous for its well-preserved medieval structures and the story behind its emblem, the Black Rooster, symbol of Chianti Classico. The village remains largely unchanged since the Middle Ages, making it an ideal place to soak up authentic Tuscan history and architecture. Expect to see ancient stone houses and enjoy peaceful vistas.

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Visiting a Family-Run Estate with Medieval Cellars

The tour includes a visit to a family-owned wine estate, where medieval cellars and oak barrels still age the region’s celebrated wines. The estate’s setting offers a tangible connection to Tuscany’s winemaking traditions, with guided explanations of the process.

Learn about how extra-virgin olive oil is produced and what distinguishes genuine olive oil from imitation. This part of the experience provides practical insights into Tuscan culinary customs, with local secrets shared by the guides. It’s a hands-on learning experience for both wine and olive oil aficionados.

Tasting 3 Top Chianti Classico Wines with Olive Oil

A major highlight is the wine tasting session, where you sample three excellent Chianti Classico wines carefully paired with a Tuscan lunch. The meal is prepared on-site using organic ingredients cultivated at the estate, ensuring freshness and authenticity.

Alongside the wines, you’ll taste extra-virgin olive oil, learning how to recognize a high-quality product. The tasting is typically led by knowledgeable staff who explain the characteristics of each wine and the importance of quality in Tuscan productions.

Authentic Tuscan Lunch on the Private Estate

The lunch takes place indoors at the estate, providing a cozy setting with views over the vineyard. The meal consists of regional dishes made from ingredients grown directly on the property, emphasizing organic and sustainable farming practices.

This is a true taste of Tuscany’s culinary traditions, with hearty yet simple flavors. The pairing of local wines and olive oil enhances the meal, creating a memorable culinary experience that complements the scenic surroundings.

Scenic Return Drive and Final Stop at Piazzale Michelangelo

After lunch, a 25-minute drive takes you back toward Florence, with a 30-minute scenic drive along the countryside. The tour concludes back at Piazza dei Cavalleggeri, where it started, rounding out a full day immersed in Tuscany’s landscapes and culture.

While the day is busy, the pacing allows time at each stop to explore comfortably and enjoy the views. The overall experience balances sightseeing, tasting, and education, making it ideal for those who appreciate a well-rounded, engaging day.

Meeting Point and Group Details

This tour departs from Piazza dei Cavalleggeri, where guides hold a sign with your name. The group size can be private or small, providing a more personalized experience. It’s recommended to inform the provider of any special dietary restrictions in advance to ensure a smooth and enjoyable meal.

The activity lasts roughly 6 hours, and booking options include free cancellation up to 24 hours before the scheduled start. You can also reserve your spot without immediate payment, allowing flexibility for travel plans.

Why This Tour Excels and Who It’s For

The high praise from previous participants highlights knowledgeable guides, especially those who are passionate about Tuscany’s history and traditions. The scenic drives, charming villages, and authentic food make the experience deeply satisfying for lovers of wine, history, and countryside views.

The visit to a family-run estate with medieval cellars, combined with the quality wine and olive oil tastings, sets this tour apart from more generic options. The lunch featuring organic, estate-grown ingredients adds a special touch of authenticity.

However, the limited time at each stop means it’s best suited for travelers who enjoy a concise yet immersive day trip. The tour’s scenic routes and casual pace make it accessible, but those with mobility concerns should consider the walking involved in the villages.

Final Thoughts on the Tuscany Chianti Private Day-Trip

This 6-hour private tour from Florence offers a well-balanced combination of scenic views, historical exploration, and culinary delights. The focus on Chianti’s best villages, wine, and olive oil makes it ideal for those seeking an authentic taste of Tuscany.

The personalized experience with an expert guide, paired with delicious regional cuisine, creates a memorable day that highlights Tuscany’s charm and craftsmanship. While it’s a busy schedule, the pace and intimate group settings ensure comfort and engagement.

For wine lovers, history enthusiasts, and those wanting a deeper connection to the Tuscan countryside, this tour provides a meaningful and enjoyable way to explore the region’s most beloved spots, all within a manageable half-day trip.

Frequently Asked Questions

What is included in the tour?
The tour includes visits to Greve in Chianti and Montefioralle, a guided walk through a family-owned estate, a wine and olive oil tasting, and a Tuscan lunch with three Chianti wines.

How long does the tour last?
The total duration is approximately 6 hours, starting from Florence and returning to Piazza dei Cavalleggeri.

Is there a minimum group size?
You can choose a private or small group experience, ensuring a personalized atmosphere.

Are dietary restrictions accommodated?
Yes, travelers should inform the provider of any special dietary requests in advance.

What are the main highlights?
Key highlights include the panoramic drive along Cassia Vetus, exploring medieval villages of Greve and Montefioralle, visiting a medieval cellar, and enjoying authentic Tuscan food paired with top wines and olive oil.

Can I cancel the booking?
Yes, free cancellation is available up to 24 hours before the scheduled activity.

You can check availability for your dates here: More Great Tours Nearby