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Experience a full-day private tour from Florence exploring Chianti landscapes, San Gimignano, Siena, and a winery with tastings, lunch, and expert guides.

The Private Chianti Full Immersion Tuscany & Wine from Florence is a thoughtfully curated day trip that invites visitors to explore the iconic Chianti region. Priced at $610.77 per person, this tour offers a 9-hour journey through some of Tuscany’s most celebrated landscapes and towns. It stands out for its small-group experience, with a maximum of 8 guests, ensuring personalized attention and a relaxed pace. The tour is led by knowledgeable guides, who share insights into the region’s wine, history, and local culture, making it ideal for those seeking an intimate and comprehensive Tuscany experience.
Pickup is available from Florence’s hotel Boccaccio, with drop-off back at the starting point. Travelers should note that most bookings are made 122 days in advance, highlighting its popularity. This tour suits visitors interested in wine tasting, medieval towns, and scenic drives, especially those who prefer a private and customized experience over larger group excursions.

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The tour begins at Hotel Boccaccio in Florence at 8:00 am. From here, a local English-speaking driver transports the small group in a Black Mercedes Minivan, which seats up to eight guests. The journey takes you through vineyard-laden hills, olive groves, and authentically Tuscan scenery, setting the tone for a day immersed in Tuscany’s countryside.
This private arrangement ensures comfort and allows for a relaxed exploration of the region, far from the crowds often encountered in larger tours. The pickup and drop-off service makes it convenient for guests staying within the historic center of Florence, with options for other locations upon request.

The first stop is at Piazzale Michelangelo, a famed viewpoint designed by Giuseppe Poggi in 1869. From this vantage point, visitors enjoy sweeping views of Florence’s skyline, with notable landmarks like the Duomo and Palazzo Vecchio visible. The 10-minute stop here offers a perfect chance for photos and to soak in the cityscape before heading into the Tuscan countryside.
This stop sets the tone for the day, emphasizing the combination of art, landscape, and history that makes Tuscany so captivating.

The tour includes about 30 minutes of free time in San Gimignano, a town famous for its tower-houses built by patrician families during the Middle Ages. Originally around 72 towers, now only 14 remain, but their presence still defines the city’s skyline. The town once served as a crucial relay point on the Via Francigena, facilitating pilgrim travel to Rome.
Visitors can explore the feudal atmosphere, browse local shops, and see the Vernaccia wine bottles, which the town is also renowned for. The limited time encourages a stroll through narrow streets, appreciating the medieval architecture and artisan crafts.

Arriving in Siena around 12 pm, the tour stops at Piazza del Campo, one of Italy’s most beautiful medieval squares. Known for hosting the Palio di Siena horse race, this city boasts a wealthy history and well-preserved medieval architecture.
Guests have about 1 hour and 30 minutes to explore, browse local markets, and enjoy lunch options. Siena’s shops offer leather goods, fabrics, glazed terracotta, gold jewelry, and local specialties like Panforte and Ricciarelli. The lively market around the Fortezza Mediceana on Wednesdays makes this stop particularly vibrant.
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A key component of this tour is the visit to a local winery in the Chianti area, where guests learn about Classico wines and olive oil production. The wine tour includes tasting a selection of Chianti wines, paired with olive oil samples, providing insight into Tuscan viticulture and olive growing.
The full lunch served at the winery complements the tasting experience, with authentic Tuscan dishes that showcase regional flavors. This part of the trip emphasizes the culinary tradition and terroir that make Chianti wines so renowned.

Throughout the day, the driver guides the group along the Chianti highway, offering commentary on the landscape, vineyards, and local culture. The vineyard-laced hills and endless olive groves make this drive a highlight in itself, offering picturesque views at every turn.
This scenic route underscores the beauty of Tuscany’s countryside, providing numerous photo opportunities and moments of tranquility.

Reviews highlight the knowledgeable guides, with Gabriele, Andrea, and Alberto praised for their insights, humor, and patience. The guides share fun facts about Italian cuisine, historical context, and local stories, making the experience both informative and engaging.
The small-group setting allows for direct interaction and personalized attention, which enhances the overall enjoyment of the day.
The tour is designed for most travelers, with confirmation received upon booking. It is suitable for those with moderate mobility, as stops involve walking through towns and uneven streets. The availability of hotel pickup and drop-off simplifies logistics, especially for guests staying in Florence’s city center.
If weather conditions are poor, the experience can be canceled with a full refund or rescheduled, ensuring peace of mind. The 9-hour schedule allows ample time for sightseeing, tasting, and relaxing.
This private Chianti tour is perfect for visitors seeking an intimate, well-rounded day of wine, culture, and scenery. It suits those who appreciate guided insights and authentic experiences, with enough flexibility to explore medieval towns and enjoy regional food and wine.
While the price point might seem high, the small-group size, full itinerary, and personalized service justify the investment for those craving a comprehensive and comfortable Tuscan adventure.
The Private Chianti Full Immersion Tuscany & Wine from Florence offers a balanced blend of scenic landscapes, historical towns, and wine tasting in a luxurious small-group setting. The expert guides, beautiful stops, and delicious regional lunch make it a standout choice for travelers wanting an immersive day in Tuscany.
While it requires advance booking and a moderate price, the personalized experience, flexible logistics, and quality of the stops make this tour a compelling option. It is particularly well-suited for those who value authenticity, comfort, and expert narration in their Tuscan journey.
“What an amazing day with friends! We thoroughly enjoyed our day with Andrea! He was a fantastic guide and driver and made our day fully enjoyable…”
Is hotel pickup available for this tour?
Yes, the tour offers pickup and drop-off from hotels and private residences in Florence’s historic zone.
How many people are in each group?
The tour is limited to a maximum of 8 guests, ensuring a small-group experience.
What are the main stops during the day?
The tour visits Piazzale Michelangelo, San Gimignano, Siena, and a local winery for tasting and lunch.
How long is the total tour?
The 9-hour experience starts at 8:00 am and ends back at the starting point in Florence.
Is this tour suitable for all ages?
Most travelers can participate, but those with mobility issues should consider walking requirements at the stops.
Can I cancel if my plans change?
Yes, the tour offers free cancellation if canceled at least 24 hours in advance, with a full refund.
What is included in the price?
The cost covers transportation, guided commentary, wine and olive oil tastings, lunch, and admission tickets to the stops.
Who leads the tour?
Guides such as Gabriele, Andrea, and Alberto are praised for their knowledge and personable approach.
Is this tour customizable?
As a private tour, it can be tailored to suit your preferences upon request.
What makes this tour stand out compared to others?
The small-group size, personalized service, and comprehensive itinerary combining scenery, culture, and cuisine make it a top choice for authentic Tuscany exploration.