Available languages
10 hours 30 minutes
Mobile ticket
DEPARTURE GUARANTEED!
Enjoy a perfect day trip visiting 3 of the most impressive places in Tuscany. Montalcino, house of "Brunello" wine; Pienza, well known for the "Pecorino" cheese and Montepulciano where the undisputed symbol is the "Nobile di Montepulciano" wine!
Please note that from November to April we cannot guarantee the restaurant with view, as stated in the inclusions.
The Valdorcia has been recognized as UNESCO world heritage site since 2004, as it was an inspiration for many Renaissance painters.
There you will be surrounded by impressive views, art, culture, amazing wine and delicious food!
Our semi private tour will be on board of a premium minivan with an english speaking driver, air conditioning and free water.
WHY CHOOSE US?
Secure bookings, Guaranted Departures!
48 hours Cancellation policy, best rates guaranteed!
Group of maximum 8 people.
Infants and small children can ride in a pram or stroller
Public transportation options are available nearby
Specialized infant seats are available
Suitable for all physical fitness levels
Florence
08:00AM: Meet our English speaking driver and let's the tour begin!
Montalcino
09:45AM: The first stop will be in a great winery in Montalcino... The winery is owned by a local family and, talking with them, you will not have the feeling to visit their work place but their home instead!...You will know everything about Brunello di Montalcino: the vineyard techniques , the wine making process, its ageing and ,off course, how to appreciate it by drinking different vintages!
2 Wine Tastings
Local product food tasting during the wine tasting in Montepulciano
Guided tour on vineyard and barrel cellar
Premium van with A/C
Superior Lunch with stunning view (November to April we cannot guarantee the restaurant with view)
English-speaking driver (driver is not the guide)
Guided tour on the underground city of Montepulciano
Gratuities
Private Pick-Up
For a full refund, cancel at least 24 hours before the scheduled departure time.
380 reviews
Total reviews and rating from Viator & Tripadvisor
140lexw,May 29, 2026
- Review from Tripadvisor
Mike our driver with Keys of Italy was amazing (driving expertly from Firenze (8:00 am pick up) to Montepulciano to Montalcino and back to Firenze) and provided us with a first hand education of the area as we passed along with a detailed description of grapes and process of wine making. First stop (1.5 hours from Firenze) was at the wine shop and underground cellar in Montepulciano; Alessandra was incredibly knowledgeable and answered all our questions; we tasted 7 wines and a dessert wine; they served local cured meats, cheese and bread (truffle oil chips were a big hit!). Then we drove to Penza for a lovely lunch at an trattoria (salad, gnocchi and tiramisu and wine of course!). Next stop (30 mins so good for a short and much needed nap!) was Montalcino - the winery and vineyards of family owned business; Arianna, one of the owners, was our guide and showed us outside the vineyards and grapes; we tasted 7 wines (rose, and Brunello reds) while she explained all the nuances of running a winery/vineyard. Then Mike took us into the ancient city of Montalcino so we could walk around see the fortress, do some shopping. Back in Firenze by 6:30 pm Strongly recommend Keys of Italy for a wonderful day long experience. Bring euros for tips for guides/drivers, comfy walking shoes, and a credit card for all the wine you will buy to ship home. (Note some places offer free shipping on a case of 12).
Cynthia P,May 27, 2026
- Review from Viator
Beautiful scenery and lovely wine. Second time taking this tour. The quality of the lunch has decreased since last year but the scenery is still wonderful from restaurant terrace. Wine pours seemed to be smaller and wine prices are up. Driver was diligent but parking was a challenge and we needed to walk further than last year to reach the restaurant in Pienza and the winery in Montepulciano. This was a bit of a challenge for me in 90+ F degree heat.
Frances G,May 20, 2026
- Review from Viator
Our group really enjoyed this tour. The winery visits and lunch were all great. Our driver, Fabio, was very good. He made a few extra stops so we could take some photos of the beautiful country side.
Teresa S,May 17, 2026
- Review from Viator
Wineries were good, driver was not kind, lunch was horrible a tourist trap. Description not correct at all
Helene G,May 11, 2026
- Review from Viator
The advertisement and confirmation receipt read "Superior breakfast with stunning views". This is totally misleading. We went on May 11th, so we expected this superior lunch with amazing views. On the contrary, we ended up in a small restaurant without any view, between 4 walls, decent lunch without more. It really disappointed us. Besides, the visit and tasting in Montepulciano were really great.
kari v,May 8, 2026
- Review from Viator
The tour was the highlight of our trip so far it was wonderful. We met new friends, and Luca was incredible. We learned not Just about wines, but the countryside and the history of the area.



Wanruo P,May 7, 2026
- Review from Viator
This is the highlight of my Tuscany trip. The two wineries have great selection of wines. I ended up bringing 5 bottles home :) Would recommend it to anyone who loves Brunello. Our driver Luca is very knowledgeable, patient and kind!


Ruy P,Apr 25, 2026
- Review from Viator
Just amazing! Private van, in our day we were only us and another couple. Our idea was to make a day to taste the wines of the region, and less tours through the cities. That's exactly what we had. First a visit to the winery Patrizia Cencione with an excellent view, complete tasting of great labels. The snack in Siena had an amazing view, the snack was good but it is already a menu with no options to exchange. After lunch we went to the Ercolani store, which has a tour full of history and a private tasting with various cheese options and embedded from the store, surprised us very much. Tours note 10 and deliver what you promise!
Giancarlo Z,Apr 24, 2026
- Review from Viator
Excellent wine tasting experience — truly one of the highlights of our trip. Everything was perfectly organized, from the beautiful setting to the thoughtful selection of wines. The guide (Luca) was knowledgeable, engaging, and made the entire experience feel both relaxed and special. We learned a lot while still having fun, and the wines themselves were outstanding. Highly recommend to anyone visiting the region, absolutely worth it.
FarAway660660,Apr 24, 2026
- Review from Tripadvisor
Luca was an incredible guide from beginning to end. He made the entire experience feel seamless, welcoming, and truly special. From the very first moment, his warmth and attention to detail stood out, and he created such a relaxed and enjoyable atmosphere throughout. We spent the day exploring some of the most beautiful places in Tuscany, including Montepulciano, Pienza, and Montalcino. The cellar visit at Ercolani in Montepulciano was very good, full of history and charm. We then had lunch in Pienza with one of the most breathtaking views we’ve ever seen, which made the experience even more magical. We ended the day at Capanna winery in Montalcino, which was truly the highlight, very special, high-end, and absolutely stunning. Luca was knowledgeable, engaging, and genuinely passionate about everything he shared. You can tell he truly cares about creating a meaningful experience, and it made all the difference. Everything felt thoughtfully guided and perfectly paced, allowing us to fully enjoy each moment without feeling rushed. We couldn’t have asked for a better guide. Thank you, Luca, for making this such a memorable day! 🍷
Operated by Keys Of Italy / Florence