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Montalcino, Orcia Valley, Pienza, and Montepulciano: Wine- and Cheese-Tasting Guided Tour from Florence

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Enjoy a rich and ripe tour through the worlds of grape and gourmet cheese. Experience art and architecture and blend it with good wines and mouth-warming specialties. You will visit the stunning Val d'Orcia and the very special towns snuggling in it. There's the chance to get to know wine cellars while nibbling on sheep's cheese. A prefect day out for the senses and the soul.
You'll start at
Piazzale Montelungo
Piazzale Montelungo, Firenze FI, ItalyPIAZZALE MONTELUNGO BUS TERMINAL, next to Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET
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  • 1
    Fortezza di Montalcino
    Stop: 3 hours -
    See details
  • 2
    Historic Centre of the City of Pienza
    Stop: 60 minutes -
    See details
  • 3
    Piazza Grande a Montepulciano
    Stop: 60 minutes -
    See details
You'll end at
Piazzale Montelungo
Piazzale Montelungo, Firenze FI, Italy
See address & details
  • Relax on a coach journey and concentrate on the Orcia Valley scenery
  • Explore Montalcino and Montepulciano as you wish, with ample free time
  • Learn about the wider Tuscany region and its hill towns from a local guide
  • Sample renowned Tuscan wine and cheese in the towns from which they originate
What to Expect
Travel from Santa Maria Novella station in Florence to the Tuscan countryside and then hop out in Montalcino, the home of Brunello wine. With your guide, call in at an acclaimed winery to taste its wares and learn about the estate’s history from the site’s wine expert. Continue with a walk through the town to admire the narrow lanes and surrounding countryside and then travel onward to Pienza. Here, explore the quintessential Italian hill town on foot, and sample its famed pecorino cheese. Before your return to Florence, there’s time for one last stop in Montepulciano, another hilltop town, famous for its namesake wine. Visit a Vino Nobile di Montepulciano cellar for a tasting and look around as you learn about the town and its delicious wine. Your day trip ends with a drop-off back in central Florence.
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Important Information
Departure Point
Piazzale Montelungo, Firenze FI, Italy
Departure Time
8:00 AM
11h 30m
Return Details
Piazzale Montelungo, Firenze FI, Italy
  • Journey by fully-fitted GT Coach
  • Expert multilingual guide
  • Free visit to Montalcino, Pienza and Montepulciano
  • Visit to a wine cellar/museum in Montalcino with tour of the wine cellars and tasting of the world-famous Brunello wine
  • Visit to a winery in Montepulciano with tasting of the “Vino Nobile
  • Cheese tasting in Pienza
  • Food and drinks, unless specified
  • Gratuities
  • Hotel pickup and drop-off
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Additional Info
  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Minimum drinking age is 18 years
  • May be operated by a multi-lingual guide
  • Please advise any specific dietary requirements at time of booking
  • Vegetarian option is available, please advise at time of booking if required
  • Please show up 20 minutes before the tour departure
  • Stroller accessible
  • Near public transportation
  • Infants must sit on laps
  • Infant seats available
  • Travelers should have a moderate physical fitness level
Cancellation Policy
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Traveller rating
  • 56
  • 9
  • 3
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  • 2
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Popular mentions
This route will give you the best scenic of Tuscany rooling hills, better than the route of “Best of Tuscany Full-day ...” but too long stop at winery shop (amost 2hrs) and very less at Pienza and Montalchino. Tour does’nt stop anywhere along road, tour guide seems ignore my
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Response from CiaoFlorence, Responsabile relazioni con la clientela at Montalcino, Orcia Valley, Pienza, and Montepulciano: Wine- and Cheese-Tasting Guided Tour from Florence
Responded 4 Dec 2019
Dear customer Thank you for your review. Please let us clarify that we do not stop, during the day, for two hours at any of the wineries where we go. Never happened, it would be definitely too much, we would not make it on time to cover the other stops during the day. The average time of our wine tastings is one hour and. Also, we stop at authentic wineries immersed in the stunning countryside, not at shops. In regards to the other point: being a shared tour (meaning that you are on board with other people) we absolutely cannot change the program according one or few clients' preferences by adding stops or just by changing them. We need to strictly respect the schedule of the tour program everybody has bought. Then, a big bus cannot stop in the middle of the street, it would be very dangerous and totally against the street rules and the security of our travellers. We hope that you will have the opportunity to come back in the future and spend one more day in Val D'Orcia, that area really deserves more than one visit :) All the best Best Regards Ciaoflorence Staff
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Amazing sight seeing and exploring of Val D'orcia !!! The wine tasting was great and the host Julia was absolutely brilliant, fun and resourceful of the Tuscan countryside. I invite all to try this beautiful tour, you won't be disappointed.
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Response from CiaoFlorence, Responsabile relazioni con la clientela at Montalcino, Orcia Valley, Pienza, and Montepulciano: Wine- and Cheese-Tasting Guided Tour from Florence
Responded 6 Nov 2019
Dear Nicola You are absolutely right, this tour is an extra value for our company because the places where we go take the customers straight into a painting! Imagine that the whole area has been declared a Unesco World Heritage Site, absolutely stunning! Thank you very much for the lovely comment, it is very much appreciated! We hope you will be back to travel with us soon :) Wishig you all the best Regards Ciaoflorence Staff
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Our first trip to Florence and we wanted to spend one full day in Tuscany tasting and sampling wines from the region, but also experience some local cheeses as well. If that's you, this trip is PERFECT! It was everything the trip described and more. Very comfortable bus
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Response from CiaoFlorence, Responsabile relazioni con la clientela at Montalcino, Orcia Valley, Pienza, and Montepulciano: Wine- and Cheese-Tasting Guided Tour from Florence
Responded 2 Nov 2019
Dear customer Thank you very much for your beautiful feedback, it makes us so happy to know that we have satisfied you 100%! We really do our best and it is delightful for us to receive such comments! We wish you all the best and we do hope you will get the chance to come back and explore more with us :) Kind Regards Ciaoflorence Staff
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We did two tours and our Tour Leaders were equally addressing and informative. We saw and did many a thing and everything was so well organised. Except for the first tour of 78 people on a double decker bus. So when we reached Sienna and there were 4 other tour groups from
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This day was jam packed and fantastic. We saw three beautiful towns, with two fabulous wine tours. The highlight of the tour was the Brunello tasting in Montalcino, we tried two wines with a phenomenal view (pic attached). This winery has been run by the same family for 27
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Response from Freedom41697695005, Guest Relations Manager at Montalcino, Orcia Valley, Pienza, and Montepulciano: Wine- and Cheese-Tasting Guided Tour from Florence
Responded 22 Oct 2019
Dear client We are so happy to receive your beautiful, exhaustive review. We are sure it will be very helpful for the other travelers to plan their trip. This tour is definitely a masterpiece tour, taking place in one of the most gorgeous areas in the world :) We wish you to come back soon and get the opportunity to explore more of our beautiful Italy :) Regards Ciaoflorence Staff
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About the operator
By: Ciao Florence Tours and Travels
Helen F
Interesting details form the tour guide
Our tour guide was very informative and his little asides and opinions made the tour more interesting. Lovely
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Helen F
Fabulous tour, well worth the money!
All three cities were well worth the visit and absolutely beautiful. The lunch and wine tasting at the vineyard
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Good tour for the price
Good tour. Worth the money. Would have liked more time at each stop but you get what you pay for! Tour bus was
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New York City, New York
Great Tour Company!
This tour was excellent: very convenient with bus ride to Pisa and back. Tour guides were very good and
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City break
Had a wonderful time views exceptional tour guide very knowledgable . Well worth a visit although all those steps
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Jane Brown
A great busy day.
A really busy day exploring three beautiful cities. I wish I had more time exploring Sienna and more time would be
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David S
Great visit to wine country
My wife and I spent a week in Florence and had the opportunity to take some day trips. We were fortunate to
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Matthew G
United States
Tour if short on time in Italy.
The tour was a must if you’re strapped on time while visiting Italy. FYI, full bus (50+ people). The tour guide
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Glasgow, United Kingdom
Very poor customer service! Avoid!
We booked this wine tasting tour and the voucher had very unclear instructions on meeting point! We arrived at the
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Great! that's all
The tour of Tuscany has been the best choice since we arrived in Florence, a day full of information, Juliano was
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Key Details
  • Duration: 11h 30m
  • Mobile Ticket Accepted
  • Instant confirmation
  • Languages Offered: English, Spanish
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