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Discover the beauty of Tuscany with a private day trip from Florence to Montepulciano, Pienza, and Montalcino, including expert guides and comfortable transport.

This $464.43-per-person tour offers a full-day experience to three of Tuscany’s most renowned towns: Montepulciano, Pienza, and Montalcino. Starting from Florence, the journey lasts approximately 9 hours, including hotel pickup and drop-off, making it an accessible way to see the countryside without the hassle of driving.
The tour features comfortable Mercedes Vclass minivans and a private group setting, guided by knowledgeable drivers who provide insights along the way. While lunch and wine tastings are not included, the flexibility to explore each town independently makes this trip ideal for those who want an intimate and relaxed experience of Tuscany’s highlights.
One key consideration is the timing: the tour departs at 8:30 am, and the stops include Montepulciano for 1 hour 30 minutes, Pienza for 1 hour, and Montalcino for 1 hour 30 minutes. Given the pace, visitors should be prepared to enjoy each town at a leisurely pace, but some may wish for more time at each stop.

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This private day trip begins with hotel pickup in Florence, removing the need to navigate busy streets or arrange separate transportation. The Mercedes Vclass minivan provides a smooth, comfortable ride, with fuel surcharge included in the price. The driver/guide stays with the group, offering commentary and assistance throughout the day.
The return to Florence is scheduled for late afternoon, giving ample time to relax after a day of sightseeing. The group size is limited to your private party, ensuring a personalized experience. This setup suits visitors who prefer a hassle-free day with the comfort of door-to-door service.
Montepulciano is the first stop, reachable in under 2 hours from Florence. Built along a narrow limestone ridge, this town is famous for Renaissance palaces and beautiful churches. It is particularly renowned for Vino Nobile, a highly regarded Tuscan red wine.
During 1 hour 30 minutes of free time, visitors can stroll through the winding streets, admire the architecture, and visit local wine shops. Many choose to enjoy tasting the local wines or visiting the imposing Renaissance palaces that line the town. The town’s elevation offers stunning views of the surrounding countryside, making it a memorable first stop.

In the late morning, the tour moves on to Pienza, situated among the rolling hills of the Val d’Orcia. Known as the ideal Renaissance city, Pienza was designed to exemplify harmony and beauty in urban planning.
This short drive offers scenic vistas of Tuscany’s iconic landscapes. In 1 hour of free time, visitors typically walk through the quaint streets, visit the Pienza Cathedral, and soak in the atmosphere of this UNESCO World Heritage site. Many take the opportunity to enjoy a casual lunch or buy local products such as Pecorino cheese, which the town is famous for.

The last stop is Montalcino, perched atop a hill with a 14th-century fortress still standing today. Known internationally for Brunello di Montalcino, this town offers a perfect blend of history and wine culture.
1 hour 30 minutes here allows time for sightseeing and, for those interested, sampling some of the world’s finest wines. The town’s fortress provides panoramic views, and the narrow streets invite exploration. Many visitors choose to visit a local winery or enjoy a glass of Brunello during their free time.

While wine tasting is not included in the standard package, the tour’s flexible schedule allows visitors to add this experience. The option to visit top-rated wineries enhances the day for wine enthusiasts, offering tastings of Brunello or other regional wines.
This customizable feature can be arranged at booking, making the tour appealing to those wanting to deepen their connection with Tuscany’s viticulture. For others, the free time at each town is ample for sightseeing, shopping, or simply relaxing with a local coffee or gelato.

The Mercedes Vclass minivan ensures comfortable transportation throughout the day. The driver/guide provides local insights, answers questions, and makes the journey more engaging. The private tour aspect guarantees your group’s exclusivity, allowing for a personalized experience free from large crowds.
This setup is ideal for those seeking convenience, comfort, and expert guidance without the complexity of planning multiple separate excursions. The fuel surcharge is included, so there are no hidden costs for transportation.

This 9-hour private tour caters to culture lovers, wine enthusiasts, and visitors who want an efficient, comfortable way to see Tuscany’s iconic towns. It’s perfect for those who appreciate flexibility in their sightseeing schedule and prefer guided transport over self-driving.
People with moderate physical fitness will find the walking manageable, though some terrain in the towns may require step navigation. The option to include wine tastings makes it especially appealing for connoisseurs eager to sample regional specialties.
While the tour provides a rundown, the timing is tight, and some may find the 1-hour stops in each town just enough to get a taste of their charm. For visitors wanting more immersion or time in each location, this trip might feel rushed.
Plus, lunch and wine tastings are not included, so guests should budget for meals and beverages separately. The pickup time at 8:30 am means early mornings, which is typical for full-day excursions but worth noting for those with later travel plans.
This private day trip from Florence offers a well-balanced mix of scenic drives, cultural sightseeing, and optional wine experiences. The expert driver-guides and luxurious transport ensure comfort, while the flexible schedule allows individual exploration within each town.
Ideal for small groups or private parties, the tour stands out for its ease of access and personalized service. Visitors who want to see the highlights of Montepulciano, Pienza, and Montalcino without stress will find this tour a worthwhile choice, especially with the option to customize with winery visits.
While some may wish for more time at each stop, the overall package provides a thorough introduction to Tuscany’s famous hill towns in a single day, making it a convenient choice for many travelers.
“Alex was a wonderful guide on our first trip to Tuscany. He was very knowledgeable about the area and made it very easy for us to navigate our way…”
Can I customize the wine tasting experience?
Yes, it’s possible to add on visits to top-ranked wineries during the tour, allowing for tastings of Brunello or other regional wines.
What is included in the tour?
The tour includes private transportation on a Mercedes Vclass minivan, fuel surcharge, and a driver/guide. Hotel pickup and drop-off are also included.
How long do I have in each town?
You get approximately 1 hour in Pienza and 1 hour 30 minutes in Montepulciano and Montalcino. This allows for sightseeing, shopping, and a quick taste of the local ambiance.
Is this tour suitable for all physical fitness levels?
Yes, the walkability is moderate, but some terrain may require light physical activity. Travelers should be comfortable walking on uneven surfaces.
Can I include lunch and wine tastings?
Lunch and wine tastings are not included but can be arranged as add-ons at the time of booking for a more immersive experience.