Private Montepulciano & Pienza Day Trip from Florence
Description
Experience Tuscany on a private full-day Montepulciano and Pienza tour from Florence, traveling in comfort with an English-speaking chauffeur in a luxury Mercedes-Benz vehicle. This itinerary combines medieval towns, world-class wine, and iconic Tuscan food traditions. Explore the elegant streets of Montepulciano, enjoy a winery visit featuring the renowned Vino Nobile di Montepulciano, and continue through the Val d’Orcia for a cheese tasting and lunch centered around Pecorino di Pienza. Unlike group tours, this experience is fully private and customizable, offering door-to-door service, relaxed pace, and the flexibility to adapt the day to your interests. While visits are unguided, your chauffeur will share local knowledge, history, and cultural insights throughout the journey. Operated by Best Rome Driver, a trusted Italian company with nearly 20 years of experience, this tour guarantees reliability, professionalism, and a high standard of service throughout your day in Tuscany.
Tour Options
Itinerary
Pickup directly from your accommodation or preferred location in Florence. Meet your English-speaking chauffeur, who will be at your disposal for the full day in a luxury Mercedes-Benz sedan or van. During the drive, your chauffeur will share historical context, local traditions, and insights into the Tuscan countryside you’ll be crossing.
Arrive in Montepulciano, a stunning hilltop town known for its Renaissance palaces, stone streets, and sweeping views over the Val d’Orcia. You’ll have time to stroll through the historic center, explore small shops, and enjoy the atmosphere of one of Tuscany’s most elegant wine towns. Highlights you may see include : Piazza Grande, Historic palazzos and noble residences, Panoramic viewpoints over the countryside
After the town visit, meet your driver and continue to a local winery just outside Montepulciano. Here you’ll enjoy a tasting of the area’s most famous wines, including Vino Nobile di Montepulciano, produced from Prugnolo Gentile grapes and known for its structure, elegance, and aging potential. The tasting is typically accompanied by local products such as olive oil or light Tuscan appetizers. Note : Wine tasting is not included and is paid directly at the winery. We reserve the visit in advance.
Continue through the rolling hills of the Val d’Orcia to the Pienza countryside, where you’ll stop at a traditional local cheese factory. Here you can enjoy a tasting and lunch centered around Pecorino di Pienza, one of Tuscany’s most celebrated sheep’s-milk cheeses, often paired with honey, jams, cured meats, and local wine. Pienza is known all over the world for its production of 'pecorino cheese' and for its traditional Tuscan cuisine. Note : Tasting and lunch are not included and are paid directly on site. Reservations are arranged in advance.
In the afternoon, your chauffeur will take you into Pienza itself, a UNESCO World Heritage town designed during the Renaissance as an “ideal city.” Enjoy free time to stroll through its elegant streets, artisan shops, and scenic terraces overlooking the Val d’Orcia. Highlights you may see include : Piazza Pio II, Pienza Cathedral, Panoramic viewpoints over the Val d’Orcia
Relax during the scenic drive back to Florence, with drop-off at any location of your choice.
Highlights
What's included
Pickup Locations & Times
The pick up location of the guests is their Custom Accommodation in Tuscan City.
Traveller Ratings
Important Information
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Specialized infant seats are available
- Suitable for all physical fitness levels
- Foldable wheelchairs only, which must fit in the vehicle trunk
- Guests has to be able to get in and out of the vehicle independently
Reviews(10)
This was an amazing experience! We toured montepulciano, Pienza and Val d’orcia with peppino and it was the best experience we’ve had so far in Italy! Pep was very kind, friendly and extremely professional. The places we visited were out of this world. The cheese was good! We travelled with our 11 month old son and they provided a car seat! The itinerary was tailored to suit our needs. Very thankful for this tour company and experience!
Alessandro was an amazing driver. He was timely and attentive during the entire tour. The Mercedes van was newer and super clean. Montepulciano is a beautiful town to walk through. Alessandro set up the winery tour and tasting/lunch which turned out to be a private tour with our lovely host, Marta. It was a highlight of our vacation! The wine was superb. We went on to Pienza which is breathtaking then back to Florence at our doorstep.
Alex and Steffano were great drivers for our group. They were very timely and communcated well. Alex gave us good information along the route. They arranged a nice winery and lunch and adaptes well as we adjusted the schedule.
Buongiorno! We truly thank you for your precious review and your support. It's always a pleasure to read that our guests are satisfied with the services we have provided them with! We look forward to showing you the rest of Italy in the future and to having you on board with us once again. Best Rome Driver Team
We had Salvatore as our private driver for 1 week. He was amazing. The best driver we could ever have asked for. Kind, friendly, knowledgeable & an expert in the Italian regions we visited. He truly made our trip one to remember.
Hello! We are so thrilled to receive such a wonderful and detailed review! We thank you very much for your feedback! We look forward to showing you the rest of Italy in the future and to have you on board with us once again. Saluti from Rome, Best Rome Driver Team
I used Best Rone Driver while In Europe. Alex Paolino was my driver and he was excellent. He was on time and very knowledgeable of the surrounding areas. I highly recommend him!
Hi Tommy! Thank you for your review! We are really pleased to hear that you had a great Rome experience with us and your trip went smoothly. We look forward to helping you plan more adventures in the future! Saluti from Rome, Best Rome Driver Team
Alex is very excellent at his job. He is very knowledgeable and carrying about his position. He explained everything to us on were to eat go shopping and he took good care of us . He is a very caring gentleman . We had a good time to be with Alex . He made us laugh all the time and is a very safety driving . He is very great at his job and I would recommend him to anybody to take the tour with Alex . Very relaxing and joy able the whole entire time while we were with him . Always on time to pick us up and drop us off and always explained things when we went by to go to our next destination .
Hello! Grazie for your review of our services. Glad to hear you had a great time with us! We are looking forward to meeting you again soon and showing you the rest of Italy on board with us. Best Rome Driver Team
Alex was wonderful! He knew exactly where we needed to go and was able to get us a great wine tour at a fabulous winery. He’s very knowledgeable about the area and just a joy to be around. I highly recommend him.
What a great way to spend our final day in Italy! Our guide, Alex Paolini was terrific. He was wonderful in communicating with us ahead of time. He was right on time and even brought water and pastries. A terrific driver, he knew exactly where to go. He called a winery in Montepulcito from the car and arranged a tasting, tour and lunch. Such a great experience. I would highly recommend Alex and this tour. Get out of Rome for a day and enjoy beautiful Tuscany!
From the moment Alex arrived at our hotel for our day in Tuscany, everything ran smoothly He even had a welcome gift which we thoroughly enjoyed eating Serena was so helpful and accommodating when I was planning our excursion Due to some issues during our trip we had to change plans a few times and she was extremely helpful Would highly recommend
Absolutely amazing trip with a great driver, gorgeous views, and entertaining experiences. Alex, our driver, was so professional and kind. He even helped us when we lost an item. I highly recommend this tour!! Wine cellar was so cool (in both ways — best A/C in Italy!). Alex helped walk us through the itinerary and made sure we were in the right places at the right time.
