Val d'Orcia private tour: Montalcino, Pienza and Montepulciano

Recommended by 97% of travelers

Badge of Excellence

Florence, Italy

10 hours (approx.)
Pickup offered
Group discounts
Mobile ticket
Offered in: English

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Overview

Tuscany's Val d'Orcia is famous for its postcard-perfect scenery and hill towns, but getting around by public transportation can be frustrating. With this private tour, enjoy hassle-free pickup in Florence and soak in the views while your professional driver takes on the tricky country roads. Spend time exploring the villages of Montalcino, Pienza, and Montepulciano plus stop to snap photos of the Madonna di Vitaleta Chapel.

Visit three Tuscan hill towns in the Val d'Orcia in a single day
Plenty of stops to snap photos of the scenery along the drive
Sightsee at your own pace in Montalcino, Pienza, and Montepulciano
Taste classic Tuscan specialties and wine over lunch (own expense)

What's Included

Fully-fitted Mercedes vehicle with Free Wifi on board
Door to door Hotel pickup and drop-off
Expert Professional Driver at your full disposal for 10 hours
Air conditioning and USB charger on board
Direct access to the historic centre of UNESCO Listed Art Cities
Commentary on board
Dedicated office support available before, during, and after the tour for any assistance.
Photo stops along the route to capture Tuscany’s most stunning landscapes
Bottled water
Independent sightseeing of Montalcino, Pienza, and Montepulciano
Flexible itinerary with the option to customize your experience by adding optional services

Gratuities

Meeting and Pickup

Pickup points

Select a pickup point

Pickup details

Your private driver will pick you up directly at your hotel or apartment in Florence (if centrally located)

Itinerary

Florence

2 hours • Admission Ticket Free

Montalcino

2 hours • Admission Ticket Free

Cappella Madonna di Vitaleta

30 minutes • Admission Ticket Free

Terrapille Farmhouse

30 minutes • Admission Ticket Free

Pienza

1 hour • Admission Ticket Free

Montepulciano

2 hours • Admission Ticket Free

Florence

2 hours • Admission Ticket Free

Additional Info

Confirmation will be received at time of booking
Infants must sit on laps
Infant seats available
Not recommended for travelers with back problems
No heart problems or other serious medical conditions

Stroller accessible
Not wheelchair accessible
Travelers should have a moderate physical fitness level
This is a private tour/activity. Only your group will participate

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Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Reviews

4.9

based on 34 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

Amazing full day in 3 charming towns

Elisa_B, Apr 2026

We had an absolutely amazing day on the Val d’Orcia private tour visiting Montalcino, Pienza, and Montepulciano. Each town was uniquely beautiful and full of charm, with stunning views of the Tuscan countryside at every turn. The Brunello wine tasting was a true highlight—exceptional wines at a continuous family run vineyard going back 27 generations (1500's). The luncheon at a local farm, complete with thoughtful wine pairings, was equally memorable and gave us a real taste of the region. Although the weather was cold and windy, it didn’t take away from the experience at all—we still fully enjoyed the breathtaking landscapes and atmosphere of these incredible towns. A special thank you to Christian, our driver, who was knowledgeable, friendly, and a true pleasure to spend the day with. This tour was a perfect way to experience Tuscany, and we would highly recommend it to anyone visiting the area.

Top 3 Life Experience

Kareem_G, Dec 2025

This was a top 3 experience in my entire life. Seeing the country side of Tuscany during the fall with our amazing tour guide Christian took my breath away. Beautiful experience through and through. From our Brunello wine tasting to walking through the streets of Montalcino, Pienza and Montepulciano to Christian’s recommendations at each stop. Absolutely amazing experience. It’s a long day so be ready but it was worth every Euro spent!

Through the heart of Tuscany

Cal_S, Jun 2025

We had a wonderful day with Cristian who guided us through this beautiful area! It was appreciated that he customized the day to allow for our wants while still showing those sights promised…ending with a tasting of Brunellos below the fortress walls of Montalcino

Wine and Tuscany life

Nancy_B, Oct 2024

We loved the drive out to the three villages. Mr. Tiziano was a good driver and our car was comfortable. He was very helpful in guiding us to the highlights of each township. And these villages are a perfect representation of Tuscany life and the ancestral history.

Tuscan Sun

Courtney_C, Jun 2024

This tour is the perfect escape out of busy Florence. Ancient roads lined with spiraled cedars, roaming hills, and bell towers galore. This was my favorite day in Italy.

Outstanding Tour

Matthew_M, May 2024

Christian was an outstanding tour guide. He went above and beyond to ensure we dodged the rain clouds and hit all the right spots. Tuscany is a dream land and Christian was the perfect local guide to make sure we had the best experience.

Awesome Tuscany Day Trip

Garry_R, May 2024

We had such a great day on this tour. And our driver Tiziano made it so much better. He made some extra stops and suggestions to show us the best of the Tuscany countryside. Would recommend this for anyone who wants a real taste of Tuscany.

Awesome Day visiting some great wine towns.

Robert_M, Sept 2023

We were picked up by Clint at our hotel and traveled the beautiful countryside on our way to Montalcino where we enjoyed tasting of some of the best Brunello wines. Next stop was a beautiful small church with scenic countryside views. Then we stopped in Pienza, a quaint small city with plenty of places to have a nice lunch. Completed the day with a stop in Montepulciano for some more tastings of Nobile grapes. Overall an awesome experience 👏🍷😎

Private chauffer, not truly a tour

Sweenly_L, Oct 2021

The driver was friendly and the ride was comfortable. This is not so much a tour as much as it was just a private driver. The driver did know the lay of the land well and drove us to plots of land that were in movies. He gave us general factoids, but not in depth with history or recommendations for the actual cities we were visiting. I don't think this was worth the value (~$200/usd per person x 4). I think it was also off-season (early Oct) so driving through was not as breath-taking as the pictures. We had friends visiting Florence during the same time and they were able to hire a private driver for 1.5 hr trip out of the city for ~150 euros in total (not measured per person).