Val d'Orcia private tour: Montalcino, Pienza and Montepulciano
Traveler rating
4.9/5
Based on 39 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Val d'Orcia private tour: Montalcino, Pienza and Montepulciano worth booking?
Val d'Orcia private tour: Montalcino, Pienza and Montepulciano is a 10-hour experience in Florence, Italy, from $624 per person. It scores 68 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.9/5 rating across 39 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 68 / 100
- Rating
- 4.9/5 (39)
- Duration
- 10 hours
- From
- $624 per person
Experience the heart of Tuscany on a private journey through Val d’Orcia, chauffeured by your personal driver. Relax and enjoy the ride through rolling hills, cypress-lined roads, and storybook villages. Your first stop is Montalcino, home of the world-famous Brunello wine. Explore its cobbled streets, wine shops, and Romanesque churches. Continue to Pienza, a hilltop Renaissance gem offering sweeping views over the valley. Reimagined by Pope Pius II, it’s known for its harmony, beauty, and delicious Pecorino cheese. Along the way, stop at the iconic Chapel of the Madonna di Vitaleta, one of Tuscany’s most photographed landmarks, perfectly framed by cypress trees in an unforgettable setting. Then, visit the nearby fields featured in Gladiator, where Russell Crowe’s character walks through golden wheat toward his home. End your day in Montepulciano, famous for its Vino Nobile and elegant Renaissance charm. Discover Tuscany’s soul through its landscapes, flavors, and timeless beauty.
What you get
About this experience
Experience the heart of Tuscany on a private journey through Val d’Orcia, chauffeured by your personal driver. Relax and enjoy the ride through rolling hills, cypress-lined roads, and storybook villages. Your first stop is Montalcino, home of the world-famous Brunello wine. Explore its cobbled streets, wine shops, and Romanesque churches. Continue to Pienza, a hilltop Renaissance gem offering sweeping views over the valley. Reimagined by Pope Pius II, it’s known for its harmony, beauty, and delicious Pecorino cheese. Along the way, stop at the iconic Chapel of the Madonna di Vitaleta, one of Tuscany’s most photographed landmarks, perfectly framed by cypress trees in an unforgettable setting. Then, visit the nearby fields featured in Gladiator, where Russell Crowe’s character walks through golden wheat toward his home. End your day in Montepulciano, famous for its Vino Nobile and elegant Renaissance charm. Discover Tuscany’s soul through its landscapes, flavors, and timeless beauty.
What's included
Included
- Air conditioning and USB charger on board
- Expert Professional Driver at your full disposal for 10 hours
- Dedicated office support available before, during, and after the tour for any assistance.
- Commentary on board
- Door to door Hotel pickup and drop-off
- Flexible itinerary with the option to customize your experience by adding optional services
- Bottled water
- Independent sightseeing of Montalcino, Pienza, and Montepulciano
- Photo stops along the route to capture Tuscany’s most stunning landscapes
- Direct access to the historic centre of UNESCO Listed Art Cities
- Fully-fitted Mercedes vehicle with Free Wifi on board
Not included
- Gratuities
What you'll see and do
Florence
Discover the epitome of Tuscan elegance with a private journey through the UNESCO-listed Val d’Orcia, where every curve of the landscape feels like a painting come to life. Your exclusive experience begins with a personal pick-up directly from your accommodation in Florence by your private driver, ready to whisk you away in a luxury vehicle. Settle into the comfort of your plush seat and watch the scenery transform through the windows—from city charm to rolling hills, vineyards, and iconic cypress-lined roads. This spellbinding drive, lasting around two hours, offers a serene transition into the heart of Tuscany. As you glide through the countryside, your driver will ensure every detail is taken care of, offering insights or simply a quiet, seamless journey tailored to your preferences. Val d’Orcia awaits with its postcard, perfect vistas, medieval hill towns, and timeless ambiance, a curated beginning to your day of indulgence, discovery, and authentic Tuscan beauty.
120 minutes here
Montalcino
After a scenic drive through some of Tuscany’s most enchanting landscapes, your first stop invites you to slow down and savor the charm of Montalcino, the birthplace of the world-famous Brunello wine. Nestled among rolling vineyards and oak-covered hills, this medieval gem offers a taste of authentic Tuscany at its finest. Your private driver will drop you off in the heart of the town, where you’ll have an hour and a half to explore at your own pace. Wander through winding cobblestone streets, browse artisanal wine shops, and soak in the timeless atmosphere that defines Montalcino. As you make your way uphill, the town’s imposing fortress awaits—a historic vantage point offering sweeping views of the Val d’Orcia’s iconic countryside, dotted with vineyards, cypress trees, and serene country roads. When you’re ready to continue, your driver will be just a call away, ready to escort you to the next unforgettable stop on your Tuscan journey.
120 minutes here
Cappella Madonna di Vitaleta
One of the true luxuries of a private tour is the freedom to make memorable stops along the way, and few are more magical than the Chapel of the Madonna di Vitaleta. Ask your driver to bring you to this iconic site, one of the most photographed places in all of Tuscany. Set amid the rolling green hills of Val d'Orcia and framed by elegant cypress trees, the small stone chapel offers a scene of pure serenity and beauty. Beyond its postcard-perfect appearance, the site holds deep spiritual significance: local legend tells that the Virgin Mary appeared to shepherds right here, making it both sacred and visually stunning.
30 minutes here
From there, continue your cinematic journey through the Val d'Orcia with a visit to the filming location of Ridley Scott’s Academy Award-winning Gladiator. Your driver will guide you along the very path taken by Maximus, portrayed by Russell Crowe, as he returns to his home—a peaceful, dreamlike landscape of golden fields and whispering cypress trees. The view through the gates is unforgettable, evoking the emotion and grandeur of the film. Travelers typically spend about 30 minutes at each of these stops, though you're free to linger longer and soak in the quiet beauty of these truly iconic Tuscan scenes.
30 minutes here
Pienza
Next, your driver will take you to the enchanting town of Pienza, gracefully perched atop a hill with commanding views over the Val d’Orcia. Unlike any other town in Tuscany, Pienza was transformed in the 15th century at the request of Pope Pius II into an ideal Renaissance city, making it the first true example of humanist urban planning. You’ll have an hour and a half to wander through its charming stone alleyways, where every corner seems perfectly designed for beauty and balance. The atmosphere is serene and harmonious, offering a peaceful pause in your day. While you're there, be sure to sample Pienza’s famed Pecorino cheese, celebrated for its rich, distinctive flavor: a delicious taste of local tradition before continuing your Tuscan journey.
60 minutes here
Montepulciano
Your final stop of the day brings you to Montepulciano, a hilltop jewel renowned for its prestigious Vino Nobile di Montepulciano and timeless elegance. With its Renaissance palaces, grand churches, and sweeping views over the Tuscan countryside, this village is often considered the crown of Val d’Orcia. You'll have an hour and a half to explore at your leisure: stroll along its atmospheric streets, admire the refined architecture, and soak in the town’s noble charm. Film lovers may also recognize Montepulciano as the dramatic backdrop of the vampire saga New Moon, adding a touch of cinematic allure to its historic beauty. Before departing, take time to visit a wine enoteca or browse the artisanal boutiques for unique, last-minute souvenirs. Whether it’s a fine bottle of Vino Nobile or handcrafted goods, Montepulciano offers the perfect ending to a day steeped in Tuscan luxury and culture.
120 minutes here
Florence
When you're ready to return to Florence, simply sit back, relax, and enjoy the comfort of your private transportation as your driver takes you directly to your accommodation. It’s the perfect way to end a day filled with beauty, history, and indulgence. Don’t miss the chance to experience the postcard-perfect landscapes of Val d’Orcia in the most seamless and luxurious way.
120 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers.
Options you can book
Private tour in English
Pickup included
English Tour with Wine Tasting
Montalcino's Brunello Tasting: Choose this option to enhance your private tour with an exclusive tasting of the world-famous Brunello di Montalcino. Pickup included
Spanish Tour with Wine Tasting
Montalcino's Brunello Tasting: Choose this option to enhance your private tour with an exclusive tasting of the world-famous Brunello di Montalcino. Pickup included
Private tour in Spanish
Pickup included
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, it, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 8 travelers per booking
- Operated by
- Ciao Florence Tours Srl
Know before you go
- Infants are required to sit on an adult’s lap
- Specialized infant seats are available
- Not recommended for travelers with spinal injuries
- Not recommended for travelers with poor cardiovascular health
- Infants and small children can ride in a pram or stroller
- Travelers should have at least a moderate level of physical fitness
Photos
What travelers are saying
Outty’s summary of the themes that recur across 39 traveler reviews. Written by us, not quoted from reviewers.
The guide
8 mentionsTravelers single out the guide as the reason the experience works.
Food and drink
6 mentionsThe tastings and food stops are a highlight for most reviewers.
Knowledge and storytelling
5 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
5 mentionsThe views and photo stops come up again and again.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
39 verified traveler reviews for Val d'Orcia private tour: Montalcino, Pienza and Montepulciano. Ratings and reviews provided by Viator and Tripadvisor.
A++++ Tour
Completely very satisfied with this tour and our guide, Placedo, was amazing. Very informative and went above and beyond to customize our tour with a wine with lunch pairing he set up at Poggio Rubino. Everything so awesome from the people we met, the food we ate and the wine, over the top. Highly recommend this tour as it’s in the quieter regions of Tuscany.
via Viator
wonder trip through Valentin dorcia
Valentin was amazing! Excellent driver and guide. We stopped along our trip to see multiple viewpoints, dropped off in convenient locations and Valentin was prompt with communication.
via Tripadvisor
Great tour, highly recommend
We had a great time at the winery, the host was very friendly and passionate. The scenery was beautiful and the wines we had were excellent. Would definitely recommend.
via Tripadvisor
Tuscany wine tour
Cristian was extremely knowledgeable and made the tour exceptional. Could not have had a better tour guide.
via Tripadvisor
Honeymoon
I loved it! It was the most amazing views and wine tasting, better than I could have imagined Our tour guide Cristian was very educated on the rich culture and history! My husband and I recommend for honeymoon experience
via Tripadvisor
Good to know
- Duration
- 10 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $624 to $1,140
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 14
- Verdict
- Solid Choice
Who runs this experience
Operated by Ciao Florence Tours Srl, who run 68 experiences we rank across 9 cities, with an average Outty Ranking of 61.8 and 1 in the 90+ Club.
See everything Ciao Florence Tours Srl runsWhy this scores 68
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Val d'Orcia private tour: Montalcino, Pienza and Montepulciano: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Val d'Orcia private tour: Montalcino, Pienza and Montepulciano cost?
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Prices start at $624 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Florence usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Val d'Orcia private tour: Montalcino, Pienza and Montepulciano take?
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Plan for about 10 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Florence is not rushed.
Is Val d'Orcia private tour: Montalcino, Pienza and Montepulciano worth it?
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It holds an Outty Ranking of 68 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.9/5 across 39 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Florence, and how flexible the cancellation terms are.
Can I cancel or reschedule Val d'Orcia private tour: Montalcino, Pienza and Montepulciano?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Val d'Orcia private tour: Montalcino, Pienza and Montepulciano suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 10-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Val d'Orcia private tour: Montalcino, Pienza and Montepulciano?
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Around 14 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Florence can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Florence and add a light layer if any part of the 10-hour experience runs outdoors or after sunset.
Where does Val d'Orcia private tour: Montalcino, Pienza and Montepulciano start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Florence within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Florence?
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On Outty we rank every Florence experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Best tour in Florence: Renaissance & Medici -by a storyteller, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner, Florence Pizza or Pasta Class with Gelato Making at a Tuscan Farm. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Florence?
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Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Florence?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
What is included in Val d'Orcia private tour: Montalcino, Pienza and Montepulciano?
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Included: Air conditioning and USB charger on board; Expert Professional Driver at your full disposal for 10 hours; Dedicated office support available before, during, and after the tour for any assistance; Commentary on board; and Door to door Hotel pickup and drop-off. Not included: Gratuities. Always check the voucher for the final list before you travel.
Does Val d'Orcia private tour: Montalcino, Pienza and Montepulciano include hotel pickup?
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Yes, pickup is offered for every traveler from 354 listed pickup locations in and around Florence. You can also enter a custom pickup address when booking.
What languages is Val d'Orcia private tour: Montalcino, Pienza and Montepulciano offered in?
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It is offered in English, Italian and Spanish. Pick your language when choosing a date and time, as not every departure runs in every language.
Will I get instant confirmation and a mobile ticket for Val d'Orcia private tour: Montalcino, Pienza and Montepulciano?
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Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.
Is Val d'Orcia private tour: Montalcino, Pienza and Montepulciano wheelchair or stroller accessible?
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The operator notes: Infants are required to sit on an adult’s lap; Specialized infant seats are available; and Infants and small children can ride in a pram or stroller. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to Val d'Orcia private tour: Montalcino, Pienza and Montepulciano if the weather is bad?
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It generally runs rain or shine, so dress for the forecast in Florence. Standard cancellation terms apply: free cancellation up to 24 hours before the start.
What do travelers say about Val d'Orcia private tour: Montalcino, Pienza and Montepulciano?
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Across 39 reviews averaging 4.9 out of 5, recurring themes include the guide, food and drink, knowledge and storytelling. Travelers single out the guide as the reason the experience works.
What booking options are available for Val d'Orcia private tour: Montalcino, Pienza and Montepulciano?
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There are 4 options to choose from, including Private tour in English, English Tour with Wine Tasting, Spanish Tour with Wine Tasting, Private tour in Spanish. Prices and start times differ by option, so compare them on the booking screen.
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