Val d'Orcia private tour: Montalcino, Pienza and Montepulciano
Overview
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
- 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
- Gratuities
Meeting and Pickup
Your private driver will pick you up directly at your hotel or apartment in Florence (if centrally located)
What To Expect
Book Online
Safe & secure Easy breezy Hassle‑free
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 is instant and will be received at time of booking
- Not recommended for travelers with spinal injuries
- Not recommended for travelers with poor cardiovascular health
- Travelers should have at least a moderate level of physical fitness
- Infants and small children can ride in a pram or stroller
- Infants are required to sit on an adult’s lap
- Specialized infant seats are available
Frequently Asked Questions (7)
Q: What is the cancellation policy for the Val d’Orcia private tour: Montalcino, Pienza and Montepulciano?
Cancellation Policy
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Activity code: C-6367P73
Traveler Photos
Reviews
Average 4.87 out of 5 stars based on 38 traveler reviews collected by City Sky Diving and partner sites such as Cool Destinations and TripAdvisor
Additional Info
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Frequently Asked Questions (7)
The answers provided below were previously given in response to questions from City Sky Diving customers.
Filter by:
- For a full refund, you must cancel at least 24 hours before the tour start time.
- If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the tour start time will not be accepted.
- Cut-off times are based on the tour local time (CET).
- 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.
- Gratuities.
There is no minimum age for this tour, so bring your wee one along for an adventure..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Val d'Orcia private tour: Montalcino, Pienza and Montepulciano is as follows:
- Not recommended for travelers with spinal injuries
- Not recommended for travelers with poor cardiovascular health
- Travelers should have at least a moderate level of physical fitness
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Val d’Orcia private tour: Montalcino, Pienza and Montepulciano will be included in your confirmation email from City Sky Diving. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.
Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.
If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.
Oct 2026What's 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
- Gratuities
Additional Info
- Confirmation is instant and will be received at time of booking
- Not recommended for travelers with spinal injuries
- Not recommended for travelers with poor cardiovascular health
- Travelers should have at least a moderate level of physical fitness
- Infants and small children can ride in a pram or stroller
- Infants are required to sit on an adult’s lap
- Specialized infant seats are available
