Private Tour to Montalcino, Montepulciano and Pienza

Discover the authentic heart of Tuscany with a private tour to Montalcino, Montepulciano and Pienza. A refined experience among hills dotted with vineyards and historic villages.

What you can discover

Each tour is fully customizable: choose from the proposed experiences and build your unique itinerary, tailored to your desires.

BREATHTAKING LANDSCAPES

Let yourself be enchanted by the Tuscan hills, where olive trees and vineyards dance in the golden light, creating an atmosphere that seems to come out of a dream.

Brunello di Montalcino and Vino Nobile di Montepulciano

Discover Brunello, the wine that tells the “soul of Val d” Orcia with its intense and velvety character.

Pienza

Pienza is a Tuscan gem where beauty and flavors meet: among breathtaking views and stone alleys, its iconic pecorino cheese is born, offering the most authentic essence of this land.

MONTALCINO AND MONTEPULCIANO

Among the Tuscan hills, Montalcino and Montepulciano tell stories of ancient stone and great wines: timeless villages where Brunello and Vino Nobile offer intense emotions, to be experienced sip after sip.

Tour photos

WHY CHOOSE TUSCANY EXCURSIONS

Comfort, authenticity, and freedom: travel in style with local drivers with over 10 years of experience, taste authentic flavors, and enjoy a tailor-made experience built around your desires.

Included services and extra options

What's included in the tour

WHAT'S NOT INCLUDED (UPON REQUEST)

What they say about us

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Frank Qi profile picture
Frank Qi
11 October 2026
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Imagine yourself on the trip of a lifetime to Tuscany. Of course it's full of hopes and anticipation to see and taste everything in your dreams. But the reality of travel - yes, even vacation - is that the stress and pressure of trying to maximize your experiences within your limited time/energy (and money!) can detract from your trip. This is where Leonardo comes in. His white glove service unburdened us from the stress of making sure "we did everything" and provided an expert-level, reassuring and calming presence while he chauffeured us through multiple towns in Tuscany. If you are looking for a loud tour guide shouting into a bullhorn while carrying an umbrella in the air, then please look elsewhere. What Leonardo / Tuscany Excursions provide is a bespoke, professional and unique service tailored to your interests. Think of him as a Michelin star sushi chef. You can order items a la carte. Or you can surrender to his expertise and go "omakase". Either way, you won't go wrong. Highly recommend with absolutely zero reservations!
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peyton keller profile picture
peyton keller
9 October 2026
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+2
Alessandro was an amazing tour guide and driver. Showed us all the highlights and was very knowledgeable about everything. Highly recommend!
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Jerrod S profile picture
Jerrod S
23 September 2026
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We had Alessandro conduct our tour ya couple days ago and it was fantastic. Tuscany Excursions set up a great of wineries including lunch. They curated a tour based on my interests in wine and the region. Also, Alessandro was fantastic in that we had a wonderful conversation about the wine, grapes and the region history. The conversation with Alessandro was so. Helpful and informative providing us with a good contextual understanding of the area, wineries and its history. It wasn’t a tourist oriented canned presentation. We will use Tuscany Excursions again.
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Jerrod S profile picture
Jerrod S
23 September 2026
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Great wine tour We had Alessandro conduct our tour ya couple days ago and it was fantastic. Tuscany Excursions set up a great of wineries including lunch. They curated a tour based on my interests in wine and the region. Also, Alessandro was fantastic in that we had a wonderful conversation about the wine, grapes and the region history. The conversation with Alessandro was so. Helpful and informative providing us with a good contextual understanding of the area, wineries and its history. It wasn’t a tourist oriented canned presentation. We will use Tuscany Excursions again.
Posted on Google Google
joshua rodgers profile picture
joshua rodgers
21 September 2026
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Leonardo helped me craft a wonderful 8 hour day trip from Florence where my family was picked up at our door by a comfortable air conditioned Mercedes. The wineries that he suggested were wonderful with amazing wine, food and breath taking views. We would definitely engage with him again if we come back to Italy.
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Jose Triana profile picture
Jose Triana
21 September 2026
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+11
If you're looking for personalized service in Spanish, without a doubt, contact Alessandro and his team at Tuscany Excursions. Our trip started off a bit frustrating due to the difficulty of getting around, but Alessandro made our stay in Florence wonderful. He provided a luxurious city tour, picked us up at our hotel, took us to a spectacular lunch overlooking the Tuscan countryside, and transported us in a luxurious and impeccably comfortable vehicle. Punctual, attentive, and with extensive knowledge of Florentine history, he made our stay in Florence a truly memorable experience. We wholeheartedly recommend him to anyone visiting this spectacular city of Florence and looking for service in Spanish.

(Translated by Google, see original)
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joshua r profile picture
joshua r
21 September 2026
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Excelllent Florence Day Trip We had an amazing 8 hour private day trip from Florence where we visited the leaning tower of pisa as well as 2 wineries. Leonardo took care of all of the scheduling with the vineyards. The day was absolutely perfect where we got great pictures, amazing wine and delicious food. I would definitely book with this operator in the future.
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Janice M profile picture
Janice M
21 September 2026
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Day trip to Pisa and Lucca Excellent trip from Florence to Pisa and Lucca. Leonardo was very knowledgeable and a very good driver
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Jose T profile picture
Jose T
21 September 2026
Tripadvisor star 1Tripadvisor star 2Tripadvisor star 3Tripadvisor star 4Tripadvisor star 5Verified
Luxury Personalized Tour in Tuscany. If you're looking for personalized service in Spanish, without a doubt contact Alessandro and his team at Tuscany Excursions. Our trip started off a bit frustrating due to the difficulty of getting around, but Alessandro made our stay in Florence wonderful. A luxury city tour, he picked us up at our hotel, took us to a spectacular lunch overlooking the Tuscan countryside, and provided transportation in a luxurious and impeccably comfortable vehicle. Punctual, attentive, and with extensive knowledge of Florentine history, he made our stay in Florence a truly memorable experience. We wholeheartedly recommend him to anyone visiting this spectacular city of Florence and looking for service in Spanish.

(Translated by Google, see original)
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Nicole Bruno profile picture
Nicole Bruno
19 September 2026
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+4
⭐⭐⭐⭐⭐ Absolutely Fantastic Experience with Tuscany Excursions! Tuscany Excursions was nothing short of prompt, professional, personable, and knowledgeable from start to finish. Communication was excellent—from the initial email to the confirmations and questions leading up to our trip. They were always quick to respond and extremely professional. Having previously run a car service myself, I really appreciate how responsive and organized they were. The only small recommendation I would make is that they confirm with the customer the day before rather than having the customer reach out to confirm. Our driver, Leonardo, was absolutely fantastic—and I don’t use that word lightly! He was passionate, intelligent, incredibly knowledgeable, polite, and genuinely enjoyable to spend the day with. We had wonderful conversations and learned so much about the area during our drive from Florence to Siena, San Gimignano, a beautiful winery for lunch, and back to Florence. Spending a full eight hours with someone can certainly feel like a long day if the person isn’t personable, but Leonardo made the entire experience so enjoyable. We truly loved our time with him and felt like we were traveling with someone who genuinely cared about making our day special. The Mercedes van was beautiful, spotless, and extremely comfortable. Leonardo arrived early to pick us up and stayed in communication throughout the day, especially when dropping us off to explore different areas. Everything was seamless and stress-free. We highly recommend Tuscany Excursions and especially Leonardo to anyone looking for a private day trip from Florence to explore the surrounding areas of Tuscany. The service, vehicle, communication, and personal attention were all exceptional. 5 stars all around! ⭐⭐⭐⭐⭐ We would absolutely use them again!

Frequently Asked Questions

The tour lasts about 10 hours, with flexible timing to adapt to your preferences and pace.

Yes, you can choose to visit one or more wineries in Montalcino and Montepulciano with Brunello and Nobile tastings, also paired with a typical lunch.

Absolutely yes. The tour offers spectacular landscapes, historic villages, and a rich cultural experience, even without wine tastings.

Certainly. The tour is customizable based on your interests, just request it at the time of booking.

Yes, we can arrange a stop at a traditional cheese factory to see pecorino production and taste it.

BOOK YOUR MONTALCINO, MONTEPULCIANO AND PIENZA TOUR

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