Explore the enchanting landscapes and historic towns of Tuscany on the Private Tour of Chianti, Siena, and San Gimignano by Minivan. Priced for a private group and lasting 8 hours, this tour offers a personalized experience that covers iconic sights, local cuisine, and exquisite wines. The tour departs from Florence, with pick-up included in the price, making it a seamless way to see some of Italy’s most celebrated destinations.

What makes this tour stand out is its customizable approach and the chance to visit two UNESCO World Heritage sites—Siena and San Gimignano—along with the scenic Chianti region. The guide, fluent in English and Italian, leads visitors through captivating landscapes and historic centers, with plenty of opportunities for memorable photos and authentic experiences.

While the crowds at Siena and San Gimignano can be busy, the timing allows for a relaxed visit with enough time to explore each site. The inclusion of a wine tasting at a family farm adds a delightful touch for those interested in local wines and cuisine. This tour is ideal for travelers seeking an intimate, flexible day trip that balances sightseeing, culinary delights, and stunning vistas.

Key Points

Private, customizable 8-hour tour departing from Florence.
Visit Piazzale Michelangelo for panoramic views of Florence.
Explore the historic center of Siena, including Piazza del Campo and the Palazzo Pubblico.
Discover San Gimignano, known for its medieval towers and Piazza della Cisterna.
Enjoy a wine tasting and lunch at Farm Sant’Appiano in the Chianti region.
Transport is in a comfortable Mercedes van, with a professional guide fluent in English and Italian.

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From Florence’s Hills to the Heart of Siena

The tour begins with a pick-up in Florence, only available within the city. The first stop is Piazzale Michelangelo, perched on a hill overlooking Florence. Here, visitors are treated to stunning panoramic views of landmarks like the Arno River, Ponte Vecchio, and the Florence Cathedral’s dome. This spot, designed in 1869 by Giuseppe Poggi, is especially popular at sunset, offering a golden backdrop for photos. Many enjoy a gelato or a drink from nearby cafés while soaking in the cityscape.

Next, the journey heads into the medieval streets of Siena. The two-hour visit centers around Piazza del Campo, a shell-shaped square paved with brick and divided into nine sections representing Siena’s civic pride. The Fonte Gaia, a beautifully sculpted fountain, adorns the square’s center, while the Palazzo Pubblico, a Gothic masterpiece, houses the Museo Civico with works by Duccio di Buoninsegna and Simone Martini. Visitors have time to enjoy the lively atmosphere, browse local shops, or extend their visit into the Gothic palace for more art.

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Discovering the Charm of San Gimignano

After Siena, the tour moves to San Gimignano, a medieval hilltop town famous for its 13th-century towers and well-preserved walls. The Piazza della Cisterna is the town’s lively hub, triangular in shape and lined with medieval houses. The Torre Grossa, a prominent stone tower, offers fantastic views of the town and surrounding countryside. The Cathedral of San Gimignano, with Ghirlandaio frescoes in the Chapel of Santa Fina, is another highlight for those interested in art and history.

Visitors typically spend about two hours in San Gimignano, wandering its narrow streets, snapping photos of the skyline, and soaking in the medieval atmosphere. The town’s charm lies in its preserved architecture and scenic vistas, making it a perfect stop for lovers of history and photography.

Tasting Tuscany: Wine and Local Cuisine at Farm Sant’Appiano

A key feature of this tour is the visit to Farm Sant’Appiano in the Chianti region, around two hours long. This family-owned winery offers insight into wine production processes, with opportunities for tastings. Guests can sample seven different Chianti wines—a highlight for wine enthusiasts—and opt for a lunch with authentic Italian dishes (costs are separate).

The setting provides a relaxing outdoor environment with views of the rolling hills and vineyards. The friendly hosts and scenic surroundings make this a memorable experience, especially for those interested in local wines and Tuscany’s culinary traditions.

Scenic Drive Along the Chianti Wine Route

The return leg of the journey takes about two hours along the Chiantiggiana SR 222 Wine Road. This breathtaking route connects Siena to Florence, winding through vineyards and rolling hills. The driver, experienced and knowledgeable, shares insights about the landscape and local wineries as the van passes through the beautiful Chianti countryside.

This part of the tour provides a peaceful, scenic drive that showcases Tuscany’s iconic vineyard-covered hills and picturesque vistas. It’s a perfect way to reflect on the day’s highlights while enjoying the stunning scenery.

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Practical Details: Logistics and Group Size

The pick-up for this tour is included only within Florence city and takes place at Piazzale Michelangelo. The transport is in a luxurious Mercedes van, ensuring comfort throughout the eight-hour journey. The tour is designed exclusively for private groups, allowing for a personalized experience and flexibility in timing and stops.

The tour operates in English and Italian, with the driver serving as your guide. Cancellation is free if done up to 24 hours in advance, and the reserve and pay later option provides added flexibility for planning.

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Who Will Appreciate This Tour Most

This tour appeals most to visitors who prefer a private, flexible experience with a local guide who can customize the visit. It’s particularly suited for art lovers, wine enthusiasts, and those eager to see iconic medieval towns. The scenic drives, cultural sites, and wine tastings make it ideal for travelers wanting a comprehensive taste of Tuscany without the hassle of self-driving.

While Siena and San Gimignano can be crowded, the timed stops allow for a relaxed visit. The two-hour sessions at each town give enough time to explore without feeling rushed.

Summary of the Tour’s Strengths and Limitations

The Private Tour of Chianti, Siena, and San Gimignano offers a well-rounded experience of Tuscany’s highlights in a comfortable and personalized setting. The knowledgeable guide, scenic drives, and exclusive visits to iconic sites stand out. The inclusion of a wine tasting adds a delightful culinary dimension.

However, the crowds at Siena and San Gimignano can be noticeable, especially during peak times. The cost of lunch and tastings is not included in the base price, which travelers should budget separately. The tour is best suited for those who enjoy structured sightseeing with some flexibility, rather than those seeking an independent exploration.

This tour provides a comprehensive taste of Tuscany in a single day, with enough time to appreciate its beauty, history, and flavors.

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Private Tour of Chianti, Siena and San Gimignano by Minivan

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Frequently Asked Questions

Is pick-up included in the tour price?
Yes, pick-up is included if your drop-off point is in Florence city, specifically from Piazzale Michelangelo.

Can I customize the stops or add extra visits?
The tour is private and customizable, so extensions or additional stops can be arranged, such as visiting museums or extending time at wineries.

What is the guide’s language?
The driver serves as your guide and speaks English and Italian, ensuring clear communication and explanations.

How long are the visits at each site?
Typically, you spend about two hours in Siena and San Gimignano, and two hours at Farm Sant’Appiano for wine tasting and lunch.

Are meals and tastings included in the price?
No, lunch and wine tastings are additional expenses, but the visit to the farm provides a beautiful setting for tasting local wines.

What is the cancellation policy?
You can cancel up to 24 hours in advance for a full refund. The reserve now, pay later option helps keep plans flexible.

This Private Tour of Chianti, Siena, and San Gimignano offers a balanced mix of scenic beauty, historical sites, and local flavors in an intimate setting. It’s a great choice for those who want to experience Tuscan culture with personalized attention and comfortable transportation.