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Explore Siena, San Gimignano, and Chianti on a 10-hour private tour from Florence, including wine tastings, scenic views, and guided visits to historic towns.
A 10-hour private tour from Florence offers an immersive way to experience the Tuscan hills, combining visits to Siena, San Gimignano, and a Chianti winery. With dedicated transportation and a knowledgeable guide, this trip balances sightseeing, tasting, and cultural discovery. The tour is rated 4.8 by the provider, emphasizing quality and attention to detail. It’s ideal for those who want to explore Italy’s most iconic towns without the hassle of self-driving, thanks to a private group setting that ensures a personalized experience.
Travelers who appreciate scenic drives, historic squares, and world-class wines will find this tour particularly satisfying. The itinerary involves limited driving time to maximize time spent on-site, making it suitable for those who prefer a relaxed but comprehensive day out. Just keep in mind that the central meeting point is at Piazza Adua near Florence train station, making logistics straightforward.


The tour begins at Piazza Adua, close to the Florence train station, with coordinates 43.77792739868164, 11.249358177185059. Travelers meet in this central location, making it easy to access without long transfers. The group size is private, so you have the benefit of a dedicated driver and guide for the entire day. This sets a comfortable tone for a day packed with sightseeing and tasting.
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The guided tour of Siena lasts approximately 105 minutes, during which the guide leads visitors through Piazza Il Campo and Piazza Duomo. We like how the tour emphasizes scenic views and historical landmarks, giving a thorough overview of Siena’s medieval charm. Walks through narrow streets and visits to key sites reveal the city’s artistic and architectural heritage.
This part of the tour offers a deep dive into Siena’s history, with a chance to learn about its past as a powerful medieval city. The guide explains the significance of the square’s shell shape and the Palio di Siena, adding context to the sights. The short walking stretches are manageable, making it accessible for most travelers.

Next, the group visits San Gimignano, famous for its medieval towers that dominate the skyline. You get about 1.5 hours of free time to walk around, explore shops, and take photos. The guided portion introduces the town’s history as a medieval trading hub and UNESCO World Heritage site.
San Gimignano’s narrow streets and tower-filled skyline make it an ideal spot for strolling and shopping. The guide provides insights into the town’s architectural evolution and local traditions. The free time allows for personal exploration, whether to visit artisan shops or sample local gelato, including the renowned Forte dei Marmi flavor.

The highlight for wine lovers is the wine tasting at a Chianti winery, lasting about 75 minutes. The guided visit showcases world big brands like Chinati Classico, with tastings of multiple wines. We appreciate how the experience combines scenic views with educational commentary, helping visitors understand Chianti’s wine production.
The winery visit provides a relaxed atmosphere to savor tastings and learn about Sangiovese grapes, the main variety in Chianti wines. The setting often offers views of the rolling Tuscan hills, enhancing the tasting experience. This stop showcases authentic Tuscan viticulture and wine craftsmanship.
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After the winery, the journey concludes back at Piazza Adua, where the group started. The round-trip transportation ensures a smooth end to the day, easing the transition back to Florence. The flexibility of the private tour allows for a personalized pace and attention throughout the day.
This tour operates as a private group, with options for guided tours in English, Italian, and Spanish. The flexible booking system allows full cancellation up to 24 hours in advance, offering peace of mind. The meeting point is near the Florence train station, simplifying access for travelers staying in the city.
The tour’s small-group nature enhances the experience, offering more personalized explanations and comfort. Travelers are advised to communicate if they have luggage, as this may need to be accommodated within the transportation arrangements.

This tour is comparable to other full-day trips from Florence that include wine tastings and visits to Siena and San Gimignano. Many options feature lunch, but this particular tour emphasizes scenic views and guided visits with an efficient itinerary.
The provider rating of 4.8 reflects consistent quality, making it a reliable choice. For those interested in combining historic sightseeing with wine tasting, this tour offers a well-balanced day.

This 10-hour private tour provides a comprehensive yet relaxed way to explore central Tuscany’s highlights. The focus on Siena, San Gimignano, and Chianti makes it ideal for history, architecture, and wine enthusiasts. The limited driving time ensures that most of the day is spent enjoying each location rather than on the road.
The private group setting and multilingual guides create a tailored experience that suits those seeking personalized attention. While the itinerary is quite full, the pace remains manageable thanks to the carefully planned schedule.
This tour is especially well-suited for visitors who want a full-day immersion into Tuscan culture, culinary delights, and historic towns without the stress of organizing transportation or tours independently.

What is the starting point for this tour?
The tour departs from Piazza Adua near the Florence train station, at 43.77792739868164, 11.249358177185059.
How long does the whole tour last?
The total duration is 10 hours, including transportation, sightseeing, and tastings.
Are the tours guided in multiple languages?
Yes, guides are available in English, Italian, and Spanish.
What are the main stops during the tour?
Stops include Siena’s historic squares, San Gimignano’s medieval towers, and a Chianti winery for wine tasting.
Is the tour suitable for those with limited mobility?
The tour involves walking through historic towns and some uneven surfaces, so travelers should be comfortable with moderate walking.
Can I cancel the tour if my plans change?
Yes, full cancellation is possible up to 24 hours in advance for a full refund.
Do I need to communicate if I have luggage?
Yes, it’s advisable to inform the provider if you are traveling with luggage to accommodate transportation needs.
Is lunch included in this tour?
No, lunch is not included, but wine tastings and scenic views are key features.
What makes this tour different from other Florence day trips?
The private group setting and focus on Siena, San Gimignano, and Chianti with personalized guides provide a more relaxed and tailored experience.
How does the wine tasting work?
You visit a Chianti winery to sample big brands like Chinati Classico and learn about Tuscan wine production in a scenic setting.