Private Tour: Medieval Val d'Orcia by Minivan from Florence

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Explore Val d’Orcia’s medieval gems, Montepulciano and Pienza. Savor Noble Wine and Pecorino on this 9-hour minivan tour from Florence.

Duration: 9 hours

Cancellation: 24 hours

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Highlights

Val d’Orcia - Reach Val d’Orcia with a scenic two-hour drive from Florence.
Val d’Orcia is a breathtaking region in southern Tuscany, celebrated for its stunning landscapes, rolling hills, and enchanting medieval villages. Recognized as a UNESCO World Heritage site, the area is famous for its vineyards, olive groves, and roads lined with cypress…

Val d’Orcia - Reach Val d’Orcia with a scenic two-hour drive from Florence.

Val d’Orcia is a breathtaking region in southern Tuscany, celebrated for its stunning landscapes, rolling hills, and enchanting medieval villages. Recognized as a UNESCO World Heritage site, the area is famous for its vineyards, olive groves, and roads lined with cypress trees. Visitors can discover beautiful towns like Pienza, Montalcino, and Montepulciano, while savoring world-class wines such as Brunello di Montalcino and Vino Nobile di Montepulciano. Val d’Orcia perfectly combines natural beauty, history, and Italian charm.

Montepulciano - Stroll through the city center and visit the historic cellars for a noble wine tasting.

Montepulciano is a historic hilltop town in Tuscany, renowned for its Renaissance architecture and breathtaking views of the surrounding countryside. Famous for its Vino Nobile di Montepulciano, one of Italy’s premier red wines, the town features charming streets, beautiful squares, and impressive landmarks such as Piazza Grande and Palazzo Comunale. With its rich history, local wine, and scenic beauty, Montepulciano provides an authentic taste of Tuscany.

Pienza - Explore the city center and wander through the main streets.

Pienza is a delightful hilltop town in Tuscany, known for its Renaissance architecture and stunning views of the Val d’Orcia. Famous as the birthplace of Pope Pius II, it holds UNESCO World Heritage status. The town is celebrated for its Pecorino cheese, local markets, and beautiful piazzas, including Piazza Pio II. Pienza offers a perfect mix of history, culture, and picturesque landscapes, making it a must-visit destination in Tuscany.

Montalcino - Montalcino is a medieval hilltop town in Tuscany, globally acclaimed for its Brunello di Montalcino, one of Italy’s finest wines. The town provides breathtaking views of the surrounding vineyards and the Val d’Orcia, and is known for its historic sites such as the Fortress of Montalcino. With its charming streets, local wineries, and rich history, Montalcino is an ideal destination for wine enthusiasts and those looking to explore the heart of Tuscany.

What's Included

Hotel pickup and drop-off
Light Lunch in Montepulciano
Wine-tasting in Montepulciano
Wine Tasting in Montalcino upon request
Professional driver

What's Not Included

Food and drinks, unless specified
Lunch
Professional Guide

Additional Information

Departing from Florence, this 9-hour tour in a comfortable, air-conditioned minivan will immerse you in the stunning and picturesque Val d’Orcia. During this journey, you will explore the renowned Medieval towns of Montepulciano and Pienza. In addition to their rich art and architecture, these towns are particularly famous for their culinary and wine…

Location

Piazza dei Cavalleggeri

Please wait for your driver in front of the National Library

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings

4.9

(8 Ratings)

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James_c

Apr 12, 2026

Our guide Simone was... - Our guide Simone was prompt in picking us up and took us to many marvelous locations in southern tuscany. He provided interesting history and anecdotes about many sites during our drive and then he had detailed recommendations on the highlights to see, eat, drink, and experience at each one of our stops. He was incredibly generous with his time and we were all very grateful for his patience as we hit a huge amount of traffic on the way home. Every single person in my family fell asleep as poor Simone endured the long drive home. We absolutely loved this adventure and we were so grateful for Simone's kindness and expertise.

Review provided by Viator

Kathy_w

Nov 26, 2023

Thanksgiving with Francesca in Val d'Orcia - We were thrilled to be paired with Francesco as our tour guide / driver again (we had him in 2022). The drive through Val d'Orcia and the views at Pienza were breathtaking. We had a wonderful time at the Talosa Winery with Nicholas which was most informative. Our stop at Pienza for lunch was so memorable - lunch at Tratoria de Luna was superb - and the late afternoon sunset views were amazing. What a great way to spend Thanksgiving Day!

Review provided by Viator

Raminsh

Sep 25, 2023

Magic tour with fantastic friendly tour driver - The tour covers a beatifil drive through magnificent Tuscon sceneries. We covered a reasonable number of visits to Tempuo St Biagio, Montapulciano, Pienza and Montalcino. Each had their charm and beauty... We are over the moon with the experience. The tour operator communicated eith us several times becore the trip start and we were picked up in front of our accomodation the day of the trip by Simone, in a clean and very spacious van. Simone, was extremely helpful, and friendly. He explained multiple facts about the historical and geographical aspects of our visiting towns. He was very flexible and accomodated our stop/ start times whenever wecwanted to spend time in a place. We were very lucky to have him as our driver. Strongly recommend this Tour Operator and Simone!

Review provided by Tripadvisor

Orla_r

Sep 15, 2023

Beautiful Day in Tuscany - Relaxed and beautiful day seeing Tuscany and the beautiful towns of Montepulciano, Pienza and Montalcino. Simone was a great driver, very relaxed and chilled experience.

Review provided by Viator

John_k

Oct 16, 2022

Stefano was a wonderful... - Stefano was a wonderful driver / guide. He was very knowledgeable on the area and offered great recommendations for places to dine.

Review provided by Viator

812carog

Aug 5, 2019

Family tour in Val d'Orcia - Crossing the Val d'Orcia with beautiful landscapes, gentle hills, olive groves and vineyards and discovering two charming villages: Pienza & Montepulciano where it is good to walk. Visit a cellar for a wine tasting (the famous Nobile di Montepulciano) and olive oil accompanied by cold cuts and pecorino. Everything was perfect! We thank and warmly recommend our excellent guide/driver "Marco the Italian" with whom we had a very good feeling and who made us spend an unforgettable day! "Sylvano le Suisse" and family

Review provided by Tripadvisor

Joe

Jun 6, 2019

Val d'Orcia - This was an awesome trip. Our driver spoke good English and drove us around to see countryside views that we told him we were hoping to see. He had great knowledge of the area and the history of wineries, local specialties, agriculture, etc. He even found a farm to table restaurant that was off the beaten path and managed to get us in to a already full dining hall for a fantastic meal. It was a great day.

Review provided by Viator

Drbarbara_c

Apr 12, 2024

Beautiful but brace for steep walks. - Both Pienza and Montepulciano were beautiful hill towns and the Tuscan countryside around both at its best in Spring. Both towns are very steep and anyone with even slight mobility issues needs to think carefully about this day out. Our guide did his best to help us navigate the challenges but we did find the tour exhausting.

Review provided by Viator

Check Availability

From $170

up to 8 guests

1 - Adult