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Discover Tuscany's highlights with this private 8-hour tour to Siena and San Gimignano, including scenic drives, expert guides, and optional wine tastings.

This exclusive private tour to Siena and San Gimignano offers an intimate exploration of two of Tuscany’s most captivating towns, all within a carefully curated 8-hour itinerary. For a price of $925.73 per group (up to 6 guests), you gain access to scenic drives along Tuscany’s famous Chianti Roads, personalized commentary from a licensed driver and guide, and flexible options for wine tastings or a leisurely lunch. Booked on average 61 days in advance, this tour suits travelers seeking a tailored experience away from crowded group excursions.
While the tour provides an overview of major historical sites, it also offers the flexibility to include local winery visits or a relaxed lunch—an option to be arranged with the driver if desired. The air-conditioned vehicle ensures comfort during the approximately 8-hour journey, making it an ideal choice for those who want a seamless and personalized day in Tuscany.

The tour commences at 9:00am from Piazza della Calza in Florence, a convenient starting point near public transportation. The journey takes you along scenic Chianti roads, famous for their rolling hills and vineyards. The licensed driver and guide enrich your experience by sharing major and necessary information about the landscape and history of Tuscany as you drive.
Travelers appreciate the comfort of the air-conditioned vehicle, especially during the warm summer months. The personalized approach means the guide is available to answer questions or modify the stops based on your preferences, offering a flexible and engaging way to explore Tuscany’s countryside.
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Your first major stop is Siena, renowned for its medieval architecture and vibrant piazzas. The 2-hour stop allows ample time to appreciate key sights and absorb the town’s atmosphere. During this period, there are no admission fees, giving you plenty of flexibility to explore independently or simply enjoy the historic ambiance.
The guide provides major and necessary information about Siena’s landmarks, such as the Piazza del Campo and the Siena Cathedral. The structured timing ensures you experience the town without feeling rushed, and you can ask the driver about potential local winery stops or a relaxed lunch with wine tastings, which are paid separately.

The itinerary highlights San Gimignano, famous for its medieval towers and picturesque streets. Though the exact duration of this stop isn’t specified, it’s considered a key highlight of the day. Visitors enjoy wandering through the town’s charming alleys, admiring the tower skyline, and soaking in views of the surrounding countryside.
While the detailed activities during this visit aren’t specified, the overall experience promises stunning views and photo opportunities. The tour emphasizes the chance to include optional wine tastings at a local vineyard or indulge in a lunch with regional wines, enhancing the visit’s enjoyment.
A notable feature of this tour is the possibility to request stops at local wineries or for a leisurely lunch with wine tastings. These options are not included in the base price and are paid for locally. Guests have the chance to enjoy small wine tastings in authentic family-run wineries, making the experience both personal and flavorful.
This flexibility caters to those who appreciate wine culture, offering the chance to taste exceptional Tuscan wines amid scenic vineyard views. It’s advisable to communicate your preferences with the guide early in the day to optimize your experience.

The tour is operated by Tuscany Private Tours di Franco Ceccato, a provider praised for personalized service and extensive local knowledge. Many reviews highlight Franco’s ability to paint vivid pictures of Tuscany’s towns and tailor experiences to individual interests. The guide’s personality and storytelling style contribute significantly to making the day memorable.
Travelers often mention the professionalism, expertise, and entertaining commentary provided by Franco and his team. The clean, comfortable vehicle and careful attention to timing ensure a smooth, relaxed journey that balances sightseeing and leisure.

The meeting point for this tour is Piazza della Calza in Florence, easily accessible via public transportation or taxis. The tour starts promptly at 9:00am and concludes back at the same location. The private nature of this experience means only your group participates, enhancing privacy and flexibility.
Since lunch and wine tastings are paid separately, travelers should plan to bring extra funds for these activities. The free cancellation policy offers peace of mind, allowing cancellations up to 24 hours in advance for a full refund.

The personalized service, scenic drives, and flexible stops make this tour a strong choice for those who want a tailored day in Tuscany. The excellent reviews underscore the quality of the experience, with many praising the knowledgeable guides, stunning views, and delicious wine options.
Compared to larger group tours, this private experience provides a more relaxed pace and interactive guide. The upfront price covers the private vehicle, driver, and guide, offering clear value for a curated Tuscan day tailored to your interests.

This tour caters best to small groups looking for a personalized, comfortable, and informative way to explore Siena and San Gimignano. It’s ideal for families, couples, or friends who appreciate scenic drives, historical insights, and wine tastings. Travelers who prefer flexibility and customization over crowded group experiences will find this tour particularly appealing.
While the 8-hour duration and walking stops in historic towns require moderate mobility, the tour’s comfortable vehicle and flexible options accommodate most participants.
This private tour offers a well-rounded experience of Tuscany’s iconic towns in a relaxed, personalized setting. The expert guide, scenic routes, and the chance to include local wineries or a leisurely lunch make it a standout option for those seeking more than just a standard sightseeing trip.
The perfect 5-star reviews reflect consistent satisfaction, emphasizing stunning views, excellent wine options, and personalized attention. While additional costs apply for wine tastings and meals, the base experience delivers value and quality.
This tour is especially suitable for small groups who want to explore at their own pace and enjoy authentic Tuscan hospitality. It is a memorable, customizable way to experience Tuscany’s most famous towns with comfort and expert guidance.
“This was not our first trip with Tuscany Private Tours, but it is the first time I have written a review. We have visited many fascinating histori…”
Is this tour suitable for children?
Yes, most travelers can participate, and it’s suitable for families with children, provided moderate walking is manageable.
Can I include a wine tasting?
Yes, the driver can arrange stops at local wineries, but these are paid for locally and are not included in the base price.
What is the starting point of the tour?
The tour begins at Piazza della Calza in Florence at 9:00am.
How long is the drive between sites?
The itinerary involves scenic drives along Chianti roads, with about 2 hours allocated for the stop in Siena alone.
Is food included in the tour?
No, lunch and drinks are not included but can be arranged at your expense during the day.
What is the cancellation policy?
You can cancel free of charge up to 24 hours before the start; cancellations made less than 24 hours prior are non-refundable.