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Experience the beauty of Tuscany with this private 8-hour tour from Florence, visiting Siena, San Gimignano, with expert guides and local wine tastings.

The Siena – San Gimignano Private Tour offers an engaging way to explore some of Tuscany’s most iconic towns in a day. Priced at $633.82 per group (up to 8 people), this 8-hour journey provides a personalized experience with a private Mercedes vehicle and knowledgeable drivers. The tour departs from Piazza Adua in Florence at 9:00 am and includes stops at Piazzale Michelangelo, Siena, and San Gimignano, with the possibility of enjoying a Tuscan lunch either in Siena or at a local wine estate.
This tour is ideal for those seeking a comfortable, informative, and flexible day trip with a focus on Tuscan culture, history, and food. Travelers appreciate the expertise of the guides, the stunning scenery, and the chance to sample local wines. One notable feature is how the drivers combine entertainment with education, making each stop both enjoyable and enriching.
However, the tour involves long drives and walking at each location, so it is best suited for those comfortable with some physical activity and spending a full day exploring outdoor sites. The limited group size and private nature contribute to a more intimate experience compared to larger group tours.
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The tour begins at Piazzale Michelangelo, a renowned terrace offering panoramic views of Florence. This spot provides a perfect chance to take photos of the city skyline and get a sense of the landscape that shapes Tuscany. The stop lasts about 10 minutes, making it a quick but scenic introduction to the day. Visitors can enjoy the breathtaking vistas before heading south towards Siena.
This initial pause emphasizes the beauty of Florence, setting a tone of appreciation for the region’s landscapes. The free admission to this spot makes it a convenient and worthwhile start, especially for photo enthusiasts.

After the Piazzale Michelangelo, a roughly 1-hour drive in the luxurious Mercedes vehicle takes travelers into the heart of Tuscany. The private transportation is air-conditioned and equipped with parking fees and fuel costs included, ensuring a smooth ride.
During the drive, drivers share stories about the area’s wine, food, and history, adding context to the scenery. The comfort of the vehicle and the personalized attention make this part of the tour relaxing and informative. This segment also offers a chance to enjoy the changing countryside as you approach Siena.

Upon arriving in Siena, the driver leads the group into the city center, where highlights include the Siena Cathedral and the Piazza del Campo. The most beautiful parts of Siena are expertly introduced by the driver, who shares insights into local traditions and history.
Participants have about 2 hours in Siena, providing ample time to shop, take photos, and soak in the medieval atmosphere. The Duomo stands out as a main attraction, with its architectural details and art collection. Optional lunch options include a traditional trattoria, a restaurant in Piazza del Campo, or dining at a wine estate in the Chianti hills, where Tuscan cuisine and local wines are paired.

The tour offers flexibility with lunch choices. Guests can opt for a family-run trattoria in Siena to enjoy authentic Tuscan dishes or dine in a scenic restaurant overlooking Piazza del Campo. Alternatively, the wine estate lunch in the Chianti area combines homemade Tuscan food with regional wines, providing a gastronomic experience.
The two-hour window for lunch allows enough time to savor local flavors and rest before the afternoon adventures. This part of the tour emphasizes the region’s culinary richness, making it ideal for food lovers.

Post-lunch, the journey continues to San Gimignano, famous for its medieval towers and well-preserved architecture. Visitors can choose to climb the Torre Grossa, the tallest tower in the town, or enter the Cathedral to admire its artworks.
San Gimignano’s unique skyline, with towers rising above narrow streets, makes it a highlight for photography and sightseeing. During the visit, guests can also enjoy a scoop of gelato from Gelateria Dondoli, awarded as World Champion for its artisan ice cream. The hour-long stop balances exploration and relaxation, giving a true taste of Tuscany’s medieval history.

As the afternoon concludes, the tour vehicle heads back towards Florence, offering views of the Tuscan rolling hills and vineyards. The comfortable ride provides an opportunity to reflect on the day’s sights and experiences.
The private nature of the tour means guests can sit back and enjoy the scenery without the rush of larger group tours. The end point is back at the original meeting spot, ensuring convenience for travelers.

The price of $633.82 includes private transportation in an air-conditioned Mercedes vehicle, parking fees, and fuel surcharge. The tour does not include lunch, which is optional and arranged locally based on guests’ preferences.
The mobile ticket system simplifies the booking process, and the full cancellation policy offers free cancellation up to 24 hours in advance. The tour is suitable for most travelers, with most participants able to join comfortably.
The drivers are praised for being very knowledgeable, with reviews highlighting their flexibility, generosity with time, and warm personalities. Many reviews mention guides like Leonardo, Irina, Guido, and Teresa, who are noted for their expertise and engaging storytelling.
The drivers also serve as local narrators, giving insights into Tuscan culture, food, and traditions that enhance the overall experience. Their professionalism and friendliness leave a lasting impression, contributing to the high 5-star ratings.
The private setup ensures the entire day is tailored to your interests. Guests can customize the itinerary, choosing to spend more time in Siena, San Gimignano, or at a wine estate. The luxury vehicle offers a quiet, climate-controlled environment, perfect for relaxing between stops.
The flexibility and personalized attention make this tour especially appealing for those seeking a stress-free, intimate exploration of Tuscany’s highlights. The average booking time of 47 days in advance reflects its popularity among travelers looking for a well-organized day trip.
This Siena – San Gimignano Private Tour suits travelers who prefer comfort, flexibility, and in-depth insights. It’s perfect for those interested in medieval towns, local wines, and Tuscan cuisine.
The small group size and private transportation make it an excellent choice for couples, families, or small groups wanting a personalized experience. It is especially recommended for visitors who value expert guides and are eager to customize their day while exploring Tuscany’s most picturesque towns.
The Siena – San Gimignano Private Tour provides a well-balanced day of sightseeing, dining, and culture. It combines luxurious transport, expert narration, and flexibility, making it a strong choice for those eager to enjoy Tuscany in comfort.
While it involves long drives, the stunning scenery and personalized stops offset this, especially for travelers seeking a more intimate, curated experience. The high praise from past guests underscores its value and quality.
This tour delivers a comprehensive taste of Tuscany’s history, flavors, and architecture, making it suitable for anyone wanting a relaxed yet enriching day trip from Florence.
“A very memorable day with Leonardo- such a gentleman and very flexible with the itinerary and generous with his time and knowledge of the area. We …”
What is the duration of the tour?
The tour lasts approximately 8 hours, starting at 9:00 am from Florence.
How many people can join this private tour?
The tour is designed for up to 8 participants per group, providing an intimate experience.
What is included in the price?
The price covers private transportation, parking fees, and fuel surcharge. It does not include lunch.
Can I customize the itinerary?
Yes, the private nature of the tour allows for some customization, especially regarding lunch locations and time spent at each site.
Is this tour suitable for children or seniors?
Most travelers can participate, but the walking involved at Siena and San Gimignano should be considered for those with mobility issues.
Where does the tour start and end?
It begins at Piazza Adua in Florence and concludes back at the same meeting point.
How far in advance should I book?
The tour is typically booked around 47 days in advance, reflecting its popularity.
What are the main highlights of the tour?
Key highlights include Piazzale Michelangelo, Siena’s Duomo and Piazza del Campo, and San Gimignano’s towers and gelato.
What makes this tour stand out?
The personalized service, knowledgeable guides, and flexible itinerary make it an excellent choice for a detailed Tuscan experience.
Is the tour suitable for food and wine enthusiasts?
Absolutely, with options for lunch at a wine estate and local wine tastings, this tour appeals to those interested in Tuscan cuisine and wines.