Private Tour
Tuscany Countryside- Pienza and Montepulciano Private Day Trip
Overview
Available languages
10 hours
Mobile ticket
This daily excursion from Rome allows travelers to discover and enjoy one of the most beautiful countryside in the world, the famous Valle d' Orcia of Tuscany, Unesco Heritage. Moreover, you will be taken to visit two of the most beautiful towns of the Tuscany region, Pienza and Montepulciano. This tour perfectly combines Art, Food, and Relax, principles of a good life.
By specific request, we can organize a wine-tasting experience that will make the day trip even more interesting!
Additional Info
Wheelchair accessible
Infants and small children can ride in a pram or stroller
Infants are required to sit on an adult’s lap
Specialized infant seats are available
Not recommended for travelers with spinal injuries
Suitable for all physical fitness levels
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What‘s Included
Bottled water
WiFi on board
Wine tasting
Air-conditioned vehicle
toll
Cheese tasting
Lunch
Meeting and Pickup
Pickup points
Select a pickup point
What To Expect
Pienza
Pienza is a small village in southern Tuscany, in the famous Val d'Orcia! It is located about 20 km east of Montalcino and a few miles west of Montepulciano in the beautiful region of Val d'Orcia south of Siena, among soft and poetic hills and fabulous views. Pienza enjoys a truly strategic position perched on the top of a hill, overlooking the entire valley with a breathtaking view. This charming village is widely known as the "ideal" city of the Renaissance, created by the great humanist Enea Silvio Piccolomini, who later became Pope Pius II. There are several interesting places to visit, such as the Cathedral, the Pope's palace, and the suspended garden. But Pienza is also the city of cheese! Apart from its historical and artistic importance, is also the town of the cheese, the famous pecorino di Pienza for which customers will kindly be guided to experience a little tasting!
Montepulciano
The city rises on the crest of a tufa hill between two valleys, in a very suggestive panoramic place; it is a fascinating medieval town with also many Renaissance palaces. Above all the Duomo, with its beautiful frescoes by local artists! Piazza Grande is the main square. closed by beautiful palaces including the town hall with a beautiful civic tower that can be claimed to enjoy a breathtaking panorama. The famous Vino Nobile di Montepulciano has been celebrated by poets and can be considered one of the main attractions. Here there is the chance to have a wine-tasting experience and some lunch and enjoy life doing some shopping through the narrow streets of the old town.
Options
Tuscany Countryside- Pienza and Montepulciano Private Day Trip
Pickup included
Reviews
26 reviews
Total reviews and rating from Viator & Tripadvisor
Experience was...
Thomas C,
Nov 5, 2025
- Review from Viator
5.00Experience was refreshing. The countryside was so lush and pleasant with rolling Hills and so peaceful. Recommend it to anyone.
A Perfect Day in Tuscany with Alessandro
Aviana M,
Oct 27, 2025
- Review from Viator
5.00We had the most amazing day with Alessandro. He was incredibly knowledgeable, friendly, and easy to spend the day with. He really tailored the experience to fit our pace, even adjusting the schedule a bit when we decided to enjoy a longer lunch. He took us to a beautiful restaurant in Tuscany where we had a fantastic meal and some great local wine. Alessandro made sure we got to see and experience the best of Tuscany, even with our short stay in Rome. It truly felt like the perfect day, and we’re so grateful for his expertise and kindness. Highly recommend him to anyone looking for an authentic and unforgettable experience.
Tuscany Countryside Pienza and Montepulciamo
Pru F,
Sep 19, 2025
- Review from Viator
5.00Pienza and Montepulciano were both beautiful. Alessandro was a great driver and a friendly and knowledgeable guide for the day. He made choices that were perfect for the two of us and we enjoyed his company on the drive there and back. Book this tour and ask for Alessandro!
Wonderful day in Tuscany
Shannon F,
Sep 10, 2025
- Review from Viator
5.00Alessandro turned a rainy day in Tuscany into an incredible experience. I was bummed when I saw the weather forecast but honestly it all ended up working out. He is super knowledgeable about the whole region. We learned so much. He had a plan for us and was prepared so that we barely noticed the bad weather. He gave us great recommendations the whole day and made this experience so easy! I’ll be recommending this day trip to friends and family!
Our tour guide was very...
Brittainy V,
Jun 17, 2025
- Review from Viator
5.00Our tour guide was very informative, kind and helpful. The cheese tasting in Pienza was delicious. We also learned about the cheese aging process. Pienza is a small country town where you imagine sitting and sipping coffee all day. The lunch was good afterwards and my husband and I throughly enjoyed learning about the wine as well. The tour guide also made sure to know us important places such as where Russel Crowe filmed part of gladiator and stopped so we could take pictures of the scenery before actually got to the town
Wonderful Tour of the Tuscan Countryside.
Evaristo B,
May 28, 2025
- Review from Viator
5.00This is a really wonderful tour that includes the Tuscan countryside with magnificent views, visit to two of the most picturesque towns in Tuscany and excellent food and wine. Andrea was an excellent tour guide; very knowledgeable and made wonderful arrangements for us.
Tuscany - How Magical!!
Cherri B,
May 16, 2025
- Review from Viator
5.00Well worth the time to accompany Allessandro on a private tour of Pienza and Montepulciano. Allesandro’s knowledge of the area and easy going nature made the day a delight. Kept us hydrated, fed and wanting to hear more. The cheese tasting was amazing, tour of the towns and their history, wine cellar in the grotto, recommendations for a delicious lunch and wine tasting along with our own free time to explore kept us engrossed in all the region had to offer. He ensured he shared the spectacular views with us and made us wanting more. Highly recommend! Thank you so much for a lovely day and your amazing hospitality! Cherri & Scott
Highly recommend it was fantastic!
655marlog,
May 15, 2025
- Review from Tripadvisor
5.00Alessandro was the most excellent driver. He personally walked us through each town, took our pictures, and taught us the history of Italy. We will 1000% book again can’t recommend highly enough.
Wonderful private tour of Tuscany
981youngm,
Mar 24, 2025
- Review from Tripadvisor
5.00I recently booked a private tour with Alessandro to visit the Tuscan countryside towns of Pienza and Montepulciano. We enjoyed a wonderful day of seeing the beautiful Tuscan countryside by car. Our first stop was Pienza and we enjoyed the scenic views from the hilltop town as well as the charm of the small historic town. We sampled some wonderful cheeses and learned the historical highlights of the town. Our next stop was Montepulciano where we had a wonderful lunch at L'Altro Cantuccio Ristorante. We did the chef's tasting and wine pairing which was phenomenal. We also toured a wine cave that was super impressive and enjoyed a wine tasting of Vino Nobile. After a full day of touring we were returned to our hotel in Rome. Alessandro was a great guide that was fun and engaging. It also helped that with our limited Italian that he was comfortable with speaking to us in English. The historical highlights he provided were entertaining and kept us engaged. Should we be back in the area we would definitely reach out to him again as well as recommend him to our friends.
Our breathtaking Tuscany Trip
Joseph S,
Nov 15, 2024
- Review from Viator
5.00Alessandro picked us up at 8 am, who I have to say, is the best driver you will ever have. So polite, kind, and friendly, he made our trip truly a 5-star, perfect experience. We made our trek from Rome to Our first stop, Pienza, in a beautiful Mercedes Van, where Alessandro taught us about all of the towns we passed along the way to Pienza, along with simply pointing out some of the most beautiful countryside we have ever seen. Upon arrival we were greeted by s local cheese shop Alessandro recommended, where we were able to sample the best cheese my wife and I had ever had. We then were given a brief but informative tour, leaving some time for us to explore the town, and do some shopping (we bought some really cool stuff). Alessandro, showed us the best spots for pictures, and gave us some history of the town. We then headed to Montepulciano, where we were taken directly to a local winery where we not only got to do a wine tasting but also had the most incredible home-made pasta we have ever had. Please try the pici with the chianina, and the wild boar ragu. Wow….wow…wow… We then were given time to explore the town, which is much bigger than Pienza, which means, lots more shopping! So much wine, cheese, meats, wool, local artisan crafts, antique shops, etc..This town was thriving and lively, embedded with history and warm to thr touch. At wife and I explored the stretches of the town, and made our way back to our van, and headed home. The best part of our trip was our guide/driver. Alessandro, thank you, from the bottom of our hearts for such a breathtaking experience, driving through the finest areas of Tuscany. You are to be commended! My wife and I are from New York and I’ve never done anything like this before. Please book this trip and make this experience part of your lifelong memories. Thanks again, Alessandro.
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