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Discover Tuscany’s beauty on this 11.5-hour from Florence, with visits to Montalcino, Pienza, Montepulciano, plus wine and cheese tastings in picturesque towns.


The tour begins with a drive through the gentle Tuscan hills to Montalcino, a town renowned worldwide for its Brunello di Montalcino wine. Here, visitors have the opportunity to taste this famous red wine at a small, local winery. The experience blends wine preservation techniques with the town’s medieval charm.
At Montalcino, the pentagonal fortress offers panoramic views over the landscape. Climbing to the fortress provides a chance to appreciate the picturesque scenery, which includes ancient oaks, olive groves, vineyards, and cypress trees. The town’s atmosphere combines historic stone streets with the aroma of wine and local cuisine.
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Next, the journey takes travelers to Pienza, a small hilltop town. Its extraordinary views and well-preserved Renaissance architecture make it a highlight of the trip. The town is famous for local Pecorino cheese, which visitors can sample during their free time exploring the lively shops and characteristic alleyways.
In Pienza, the scenery is especially striking, with vistas over the Val d’Orcia, a UNESCO World Heritage site. The town’s compact size allows for wandering at a relaxed pace, discovering artisan products and capturing photos of its charming streets and squares.

The final stop is Montepulciano, known for Vino Nobile wine and its role as a filming location for the movie “New Moon”. Here, visitors visit a historic winery, explore cellars beneath ancient walls, and learn about wine preservation techniques.
Montepulciano’s streets are steep and lined with medieval buildings, leading up to beautiful views of the surrounding vineyards. The town also offers the chance to enjoy free time to walk and take photos, especially around the main square and famous film locations.

The tour departs from Piazzale Montelungo Bus Terminal, a 5-10 minute walk from Santa Maria Novella Train Station. Look for staff wearing fuchsia jackets to find the meeting point. The group travels on a comfortable, air-conditioned coach, ensuring a relaxed ride through the Tuscan countryside.
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An expert tour leader guides the group in multiple languages, including English, Portuguese, and Spanish. The reviews consistently praise guides like Martina, Fredrico, Jacob, Julia, Gabriele, and others for their knowledge, friendliness, and storytelling skills.
Group sizes are manageable, allowing for a more intimate experience. The guides’ ability to share historical insights, suggest local eateries, and answer questions adds to the trip’s value.
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The 11.5-hour itinerary balances guided visits with free time in each town, giving travelers the chance to explore at their own pace. Some reviews note that lunch in Pienza can take up to 2 hours, which may be long for travelers preferring shorter breaks.
The itinerary order may vary, and the schedule is designed to maximize sightseeing without feeling rushed. However, walking in Montepulciano can be challenging for those with mobility issues, due to hilly terrain and stairs.

The first wine tasting takes place at a small, characteristic winery in Montalcino. It offers a chance to sample Brunello di Montalcino, a prestigious wine that defines the region. The tasting provides insights into wine-making techniques and the importance of local terroir.

In Montepulciano, the focus shifts to Vino Nobile, a historic and renowned red wine. The visit includes exploring cellars beneath ancient walls, where stories of wine preservation are shared. The cheese tasting of Pecorino in Pienza complements the wines and adds a delicious local flavor to the experience.

While the primary focus is on wine tasting, the tour also highlights local Pecorino cheese, which is famous in Pienza. Sampling this fresh and flavorful cheese offers a taste of regional tradition and craftsmanship.
Participants should wear comfortable shoes suitable for walking on cobblestone streets and inclines. A camera is recommended to capture the scenic landscapes and charming towns.
This tour is not suitable for people with mobility impairments or wheelchair users due to stairs and steep streets in towns like Montepulciano. Large luggage or bulky bags are not allowed onboard, and pets or smoking are prohibited.
The tour offers free cancellation up to 24 hours in advance. Travelers can reserve now and pay later, providing flexibility in planning.
Ciaoflorence Tours & Travel organizes this tour, with highly positive reviews across multiple guides and drivers. Travelers consistently mention the friendly, knowledgeable guides who share interesting facts and local tips.
The group size is designed to allow for personal attention, with guides often praised for their engagement and friendliness. The comfortable coach and well-organized itinerary contribute to a smooth day.
The combination of scenic drives, cultural stops, wine tastings, and free exploration time creates a well-rounded experience. Visitors often comment that the timing and pacing are just right, making the long day on the road worthwhile.
The Val d’Orcia landscape is a highlight of this tour, with views of rolling hills, cypress-lined roads, and historic towns. The scenery is protected as a UNESCO World Heritage Site, making the visit both visually stunning and culturally significant.
Traveling aboard a luxury coach, travelers enjoy panoramic views of the Tuscan landscape, with frequent stops for photos and sightseeing. The gentle hills and vineyards provide a quintessential Tuscan backdrop throughout the day.
This 11.5-hour tour from Florence offers a comprehensive glimpse into Tuscany’s cultural and vinicultural riches. The visits to Montalcino, Pienza, and Montepulciano showcase medieval architecture, stunning scenery, and world-class wines. The inclusion of wine tastings and Pecorino cheese enriches the experience, making it ideal for lovers of good food, wine, and scenic landscapes.
While the tour involves some walking on hilly terrain, the manageable group size and expert guides ensure a comfortable and informative day. It suits those interested in Tuscany’s towns and wines, and who appreciate a well-organized, full-day adventure.
The trip provides a balanced mix of guided sightseeing and free time, with pristine scenery and authentic tastings that make it a memorable way to explore the heart of Tuscany.
How long is the tour from Florence?
The tour lasts 11.5 hours, departing from Piazzale Montelungo.
What towns will I visit?
You visit Montalcino, Pienza, and Montepulciano.
Are wine tastings included?
Yes, you enjoy two wine tastings, one in Montalcino and another in Montepulciano, featuring Brunello di Montalcino and Vino Nobile.
Is the tour suitable for people with mobility issues?
No, it is not suitable for those with mobility impairments or wheelchair users due to stairs and hilly streets.
What should I bring?
Bring comfortable shoes and a camera for photos.
Can I cancel or change my booking?
Yes, free cancellation is available up to 24 hours in advance, and you can reserve now and pay later.