




Available languages
8 hours
Mobile ticket
* Private, Exclusive, Customizable, door-to-door tour of Pienza, Val d'Orcia, Montalcino, wine and food Tour from Florence
* 8 hours in a luxury Mercedes sedan/minivan with air conditioning and knowledgeable English speaking driver
* Free Wi-Fi on board
* Refreshments on board
* Gas - Tolls - VAT
Public transportation options are available nearby
Infants are required to sit on an adult’s lap
Specialized infant seats are available
Travelers should have at least a moderate level of physical fitness
Vegetarian option is available, please advise at time of booking if required
A minimum of 2 people per booking is required
A maximum of 8 people per booking
Operates in all weather conditions, please dress appropriately
Azienda Agricola Capanna di Cencioni
Family-run boutique winery for visit and wine tasting
Pienza
Explore this quaint village on a self guided tour
Pickup included
Hotel pickup and drop-off
Free Wi-Fi on board
Round-trip private transfer
Gas - Tolls - VAT
Refreshments on board
Lunch
Gratuities
Select a pickup point
All sales are final. No refund is available for cancellations.
11 reviews
Total reviews and rating from Viator & Tripadvisor
KGMClevelandTN,Apr 4, 2026
- Review from Tripadvisor
My family spent two days with Roberto as our driver. I cannot say enough amazing things about him!!! We visited some of the most beautiful places of Tuscany during our two day tour. Roberto picked us up at our requested time at our hotel. We didn’t have to navigate to any meeting spots, and we loved that convenience. His tour was so informative on the area, art, history and culture. The breadth of knowledge Roberto had on Roman history and Italian art was impressive!! On our tour, we also had some rich experiences with small local wineries and a sheep farm that makes fresh cheese. Roberto took us to all the lovely towns in the Val D'orcia. The pace was perfect and we saw so much in the two days. We were not disappointed as we are with some tours, Roberto took us to see everything! He squeezed in all the important sights and many small, amazing lesser known places as well!!! We hope to come back and tour Umbria and Florence with Roberto sometime soon!














S1513PTjessicab,Nov 20, 2024
- Review from Tripadvisor
We had a fantastic experience with our driver, Roberto. Not only was he professional, he was authentic, knowledgeable, and personable. He knew the history of Tuscany and was able to give us recommendations to avoid the tourist traps. He was beloved by all the staff of all the wineries we visited. We've been on other private tours where the tour guide was just a driver, but Roberto was a true host and then some.
raybanb,May 27, 2024
- Review from Tripadvisor
Me and my friends had an amazing time, we were a group of 3, did a private tour from Florence to Pienza, Val D'Orcia, brunello wine and pecorino cheese tasting. Everything went smoothly, from hotel pick up to drop off. Our driver Roberto, was fantastic, he is very knowledgeable and relatable. We had conversations about almost everything, from Italian history, art, culture, all the way to life experiences, which we will remember and cherish for a very long time. We also had lunch in a farmhouse in Tuscany with Elia, who was very kind, hospitable, and welcoming. He served us local cuisines and delicacies from Tuscany, which we all enjoyed. Highly recommend this tour, they have amazing people, who will make sure you and your family/friends would enjoy your trip.
Dream13045392708,Apr 19, 2024
- Review from Tripadvisor
Excellent experience. The driver guide Roberto was simply sensational. . He demonstrated great flexibility by adjusting the itinerary to our preferences, replacing the visit to Pienza, which we already knew, with Montepulciano, and including a stop for lunch at a great restaurant in Bagno Vignoni. A very cultured and polite professional, he brought extra quality to the tour of sensational places.
demid807,Oct 4, 2023
- Review from Tripadvisor
Roberto was incredible and so knowledgeable on a variety of topics. He was funny and kept the conversation lively. He truly loves what he does and it does not go unnoticed. The wineries we went to were small production and you can tell how much passion they have for wine making. They made us feel like they were part of our family. The lunch we had was incredible and homemade. Roberto picked us up directly at our accommodation and dropped us off. I highly recommend booking with this group as they truly care about your experience in Italy. Grazie mille for a lovely experience



BETTY S,Oct 20, 2022
- Review from Viator
We had the most amazing experience exploring the beautiful wineries of Siena! Roberto truly knocked it out of the park with his charisma and incredible knowledge & passion for the local wines, giving us wonderful stories and background. We specifically love Brunello from Montalcino, and this tour gave us an excellent taste! He also took us to the most beautiful little UNESCO certified inn for a delightful lunch, with the quintessential Tuscan view and experience. Absolutely delightful experience- would highly recommend if you are a wine lover!
117willemv,Sep 13, 2022
- Review from Tripadvisor
What wonderful enjoyment of the surroundings and wine. Pienza is cozy and has good restaurants with naturally delicious wine
L8898NCjohnd,Jun 8, 2022
- Review from Tripadvisor
Our private wine tour was better than we ever imagined! We were met at our hotel in Florence by our guide, Tomas. He was very friendly and put us at ease immediately. We talked about our mutual interest in wines and imagine our surprise to find out he was a sommelier! He was very knowledgeable and helped us to understand Italian wines in an open and wonderful way. His choices of the wineries to go to and the pairing of foods with them was excellent. I would recommend Tomas and his company, We Drive You Tuscany, to anyone. He really made our winery trip memorable and special! Grazie Tomas!

Z4329SCpaulh,Mar 14, 2020
- Review from Tripadvisor
Our trip with We Drive You Tuscany was absolutely amazing!!! The friendliness and professionalism of everyone we met was incredible! Tomas recommended the perfect tour for us. It was what we were hoping for and more! On top of the amazing places we went and the incredible wine we drank, our driver Dario made the whole experience even more magical, with his knowledge, professionalism, and passion for wine! My wife and I can not wait to take a trip back to Italy and do another We Drive You Tuscany wine tour!
michaelv306,Jul 6, 2019
- Review from Tripadvisor
After weeks of research we finally decided on this tour. We knew we did not want a large group tour as the reviews looked largely terrible. We also wanted a Brunello wine tasting experience (vs Chianti) — which if you know your Italian wines — you know Brunello is the king of Tuscany. This tour had everything we wanted on paper but no reviews — so we decided to take a chance and it was by far the best experience of our 2 week Italy holiday from NYC and that was against tough competition including Milan, Florence, Cinque Terre, and Portofino! Words can barely capture this experience but here is my best attempt as we want everyone we know to book this tour. It was that memorable! Our driver, Dario, picked us up promptly at the agreed upon time at our hotel in a brand new Mercedes Benz E-class and drove us 1.5hrs to the Brunello / Montalcino wine region. Dario, recently certified as a sommelier, gave us a tremendous overview of Italian wine as well as a history lesson of the region (Tuscany, Sienna, Montalcino, etc.). My wife and I fell in love with Dario’s blend of tremendous knowledge and warm personality. He was simply amazing and we gained a friend for life. The tour itself was simply amazing and included; - 1hr stop in the charming Medieval town of Pienza where we bought amazing blocks of Pecorino cheese and walked around the quaint Medieval town. - 4-course lunch at a 1000 year old Tuscan farmhouse. The host family was so warm and welcoming. They gave us a tour of the farmhouse and then we had lunch with ingredients all sourced from their garden / farm in front of a 500-year old olive tree. Their homemade olive oil was out of this world and we bought several bottles to bring back to NYC. The food was simply amazing; easily best meal in our 2 weeks in Italy. - Brunello tasting at two amazing family owned wineries. The tastings included: Pinot Grigio, Rosso, Brunello, Brunello Reserva, and Garapa (digestivo). All were amazing! Again, the host families for each winery welcomed us as if we were family — getting to know us before starting the tour and tasting. We bought a case from each winery and can’t wait for them to arrive. The 2012 Brunello’s were simply amazing. 👌 We thought the personal touch this tour provided was invaluable and easily money well spent. We would have paid 5x what we paid. If you want the most memorable Tuscany tour of your life, we highly recommend this tour! We can’t recommend this tour enough - and ask for Dario too!!










Operated by We Drive You Tuscany