Tuscan Dream Day: Montepulciano & Pienza from Siena
Price From $177.84 per person
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Experience the heart of Tuscany on this guided small-group tour day trip to the charming towns of Pienza and Montepulciano. Travel through the beautiful clay hills south of Siena and take in the idyllic UNESCO protected landscapes of Tuscany's charming Val d’Orcia region. Explore the beautiful towns, enjoy the landscapes and have lunch on a local farm! Numbers are limited to a maximum of 8 persons on this small-group tour, ensuring you'll receive personalized attention from your guide.
Reviews
Reviews and Rating (Tripadvisor)
5 stars
Reviews by Tripadvisor travelers
Sandra_L, 10/20/2025 3:19:21 AM
Our guide, Marco, is very knowledgeable, personable and friendly. He shared a wealth of information with our group and answered all of our questions. The van was comfortable and Marco made it a very comfortable drive. It was wonderful to see the countryside and views, and have time to explore a couple of the towns along the way. The stop at the dairy farm was amazing - the view is breathtaking and the lunch was delicious. I booked this trip for my adult daughters and I - we all really enjoyed the day and are glad Marco was our host. We would highly recommend this for others looking for a small tour of Toscana!
Karen_W, 10/15/2025 4:27:48 PM
What a fun day! Our guide, Paolo, was wonderful. His knowledge of the Tuscan hills was extensive. He could answer any questions we threw at him. His driving skills were also impressive. The time flew by. We had a great bunch of travelers in our tour group. So happy to be in a small group (8 travelers.) This was a great way to see Tuscany without renting a car. We drank plenty of wine, had a lovely farm lunch and had time alone to walk around Pienza and Montepulciano, too. It felt so casual, and yet we saw so much. When it was over, I was a little sad because I wasn't going to see Paolo anymore. Take the tour. Ask for Paolo. You won't regret.
Morgan_T, 10/13/2025 3:16:01 PM
Marco was an extremely knowledgeable tour guide, I learned and laughed the entire day. Would absolutely recommend, 10/10!
Connie_V, 10/12/2025 8:53:50 AM
Great tour with a fantastic guide Marco. We had a fabulous day seeing the Tuscany countryside. Highly recommend
Willivee, 10/12/2025 5:59:52 AM
Our guide, Juliana was wonderful! Such a wealth of interesting knowledge pertaining to the area and wine. Montepulciano , Pienza, lunch, wine tasting…. Such an enjoyable and relaxing day. Highly recommend booking this tour!
Sara_B, 10/11/2025 5:23:13 AM
This trip was truly a memorable experience & one of my favorite tours in Italy! Keke was a fascinating guide, knowledgeable and full of stories about history, geography and food of the area, He was kind and open to answering questions. His energetic, enthusiastic personality made this trip extraordinary. . . So worthwhile! (and I loved the spot where we stopped for lunch -beautiful, and everything we tried was produced in house including the veggies, pasta, beer and wine). I cannot recommend this tour highly enough!
Patty_F, 10/10/2025 4:18:14 AM
This was our last tour and probably my best and favorite. Our guide was Bill/William He was a wealth of information and was so friendly and kind. I highly recommend this tour and this guide. Don’t forget to tip your guides when your done. They work very hard.
Daniel_B, 10/10/2025 3:11:17 AM
Wonderful trip through Tuscany with beautiful scenic views, stops at two charming Tuscan towns, and a delicious meal at a farm. Our guide Billy was very informative and a lot of fun. He went out of his way to make sure I could join the trip when my wife took ill that morning and I was unable to get to the pick up spot in time. Billy arranged to meet me at a closer location so I could join the trip. Highly recommend!!
G7822MSannec, 10/7/2025 8:13:17 AM
Hi, I had a great day out with my partner - we were in a mini-van with 3 other couples. We got picked up outside Basilica Cateriniana San Domenico where there is a pick up and drop off. A lot of Tour Groups are picked up there, so you need to listen out for Tuscan Escapes and someone calling your name. I really enjoyed the drive on the Crete Senesi - lovely views. We were in the back so the views were a bit restricted. Pienza is a great little town - I would have loved to stay longer. We enjoyed a very nice lunch at a Tuscan villa / restaurant with stone wine cellar - the views were great. Montepulciano is a bigger town - I recommend you look at a amp closly, let the Driver tell you on the map where you will be picked up. Our driver was fab - fun and jovial - great company for us. I highly recommend Tuscan Escapes (booked via Get your guide).
I6822JOjudithc, 10/5/2025 6:47:55 AM
Our guide William was amazing. He was fun, knowledgeable and a great relationship with the locals and the history of the area. We had beautiful weather and beautiful views and William was very attentive to our experience. Would highly recommend
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Specialized infant seats are available
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
- Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
Departure point
Meet your guide in front of the church of San Domenico in Siena at 9:30am, easy to find even if you are arriving from out of town with your own car, as there is parking in the vicinity.Return details
Experience the heart of Tuscany on this guided small-group tour day trip to the charming towns of Pienza and Montepulciano. Travel through the beautiful clay hills south of Siena and take in the idyllic UNESCO protected landscapes of Tuscany's charming Val d’Orcia region. Explore the beautiful towns, enjoy the landscapes and have lunch on a local farm! Numbers are limited to a maximum of 8 persons on this small-group tour, ensuring you'll receive personalized attention from your guide.No redemption information available
24 hours before travel date - 100% refund
Less than 24 hours before travel date - 0% refund