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Enjoy a private, customizable day trip from Florence exploring Montalcino, Pienza, and Montepulciano with wine and cheese tastings, all led by a knowledgeable driver.
The Montalcino Pienza Montepulciano WineCheese tour offers an immersive day in some of Tuscany’s most iconic towns. Priced at $1,257.16 per group (up to 8 people), this 8 to 10-hour private experience is perfect for those who want to explore with flexibility and no stress about navigation or driving. Departing directly from Florence, the tour includes private transfers, air-conditioned vehicles, and English-speaking drivers, making it especially appealing to visitors seeking a comfortable and personalized way to discover Tuscany’s renowned wine and food traditions.
A major strength of this tour lies in its customizable nature. Travelers can choose specific wineries and producers or rely on recommendations provided by the operator. The tour is well-regarded for its knowledgeable drivers, like the praised guide Giovanni, who is noted for his punctuality and expertise. While wine and cheese tastings are paid directly at each stop, the flexibility to pay as you go suits those who prefer a tailored experience. Keep in mind that this tour is only suitable for groups up to 8 and requires booking 31 days in advance on average.


The tour begins with a stop in Montalcino, a hilltop town famous for Brunello di Montalcino, one of Italy’s most celebrated wines. The town’s scenic views and historic streets set a perfect backdrop for a relaxed exploration. Travelers have the chance to visit local wineries, where wine tastings showcase the region’s signature Brunello. The driver remains on hand to offer guidance, and you can choose to add specific wineries or enjoy the operator’s recommended spots.
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Next, the itinerary takes you to Pienza, a small renaissance town rebuilt in the 15th century. Its compact streets and stunning views make for a delightful stroll. Pienza is particularly known for its pecorino cheese, which you can sample during your visit. The town’s key sites include historic landmarks visible during your walk, and the free time allows for shopping or relaxing along the picturesque streets.

The last stop is in Montepulciano, a medieval and Renaissance hill town famous for Vino Nobile di Montepulciano. The town exudes medieval charm with its narrow alleys and plethora of shops. Here, you can enjoy self-guided exploration and visit local wineries for tastings, with the opportunity to purchase local food and drink products. The free time in Montepulciano also includes shopping or simply soaking in the scenic vistas.

One of the key benefits of this tour is the ability to customize your route. You may choose to visit specific wineries or simply enjoy recommended spots provided by the operator. The wine tastings and cheese stops are paid directly on-site, allowing you to control your spending. This flexibility is ideal for those who want a tailored experience without pre-committing to particular producers.

The pickup and dropoff are included, with private transfers directly from your Florence accommodation. The air-conditioned, licensed vehicle ensures a comfortable journey throughout the day. The English-speaking driver offers commentary and local insights, turning a simple transfer into an informative part of your day. This setup eliminates the hassle of navigating Tuscan roads or coordinating multiple stops, making the tour suitable even for those unfamiliar with the region.

While the driver provides guidance and recommendations, the actual tours of towns are self-guided, giving you freedom to explore at your own pace. This balanced approach ensures a relaxed experience, with ample free time for shopping, taking photos, or enjoying a leisurely meal. The tastings are paid on-site, so you can decide whether to indulge or keep it light depending on your preferences.

At $1,257.16 per group, the tour offers a private and customizable experience suitable for groups up to 8. Booking typically occurs 31 days in advance, and free cancellation is available up to 24 hours before the experience, making it a flexible option for planning your Tuscany adventures. The tour does not include the tastings or lunch, which are paid directly, giving you the opportunity to budget according to your preferences.

Unlike many group tours, this experience emphasizes personalization and comfort. The private transfers and customizable stops allow for an intimate exploration of Tuscany’s wine and food gems. The professional driver and flexibility in choosing wineries or towns to visit make this tour particularly appealing to those seeking a tailored day without the constraints of large group schedules.
Though only one review is available, it praises Giovanni as a “perfect tour guide” who is on time and highly knowledgeable. The review also mentions that the tour was curated perfectly to match the interests in wine and food, making the experience both educational and enjoyable. Such feedback underscores the importance of expert guidance and personalized service in delivering a memorable day.
This private tour delivers a well-organized, flexible way to experience Tuscany’s famous towns, wines, and cheeses. Its customizable nature, professional driver, and free cancellation policy make it a practical choice for small groups seeking comfort and personalization. The focus on local food and wine ensures a genuine taste of the region’s culinary heritage, while the self-guided exploration allows for a relaxed, unhurried visit.
While wine and cheese tastings are paid separately, the ability to select specific wineries and pay on-site appeals to those wanting control over their tasting experiences. This tour best suits small groups, food and wine enthusiasts, or anyone looking for a stress-free, scenic, and intimate day in Tuscany.
“A perfect day with a perfect tour guide. Giovanni was on time and extremely knowledgeable. He perfectly curated the tour to our love of wine and fo…”
Is this tour suitable for a large group?
No, it is designed for groups up to 8 people, ensuring an intimate and personalized experience.
Can I choose which wineries to visit?
Yes, you can book specific wineries and producers directly or ask for recommendations, then pay on-site.
What is included in the tour fee?
The fee includes pick-up and drop-off from your Florence accommodation, private transfers in an air-conditioned vehicle, and an English-speaking driver.
Are wine and cheese tastings included?
No, tastings are paid directly on-site at each stop, providing flexibility to choose how much to indulge.
How long does the tour last?
The tour lasts approximately 8 to 10 hours, allowing ample time in each town for exploration and tastings.
Is this tour accessible for travelers with mobility issues?
The itinerary involves self-guided walking in towns, so those with mobility challenges should consider this before booking.
Can I cancel this tour if my plans change?
Yes, free cancellation is available up to 24 hours before the scheduled start.
Who operates this tour?
The experience is provided by ItalyBestExcursions, a reputable local operator specializing in private Tuscan tours.
This Montalcino Pienza Montepulciano WineCheese tour combines comfort, flexibility, and authentic Tuscan flavor, making it an excellent choice for small groups eager to enjoy the region at their own pace.