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

What you'll do

1. 1

   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.

   ⏱ 2 hours
2. 2

   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.

   ⏱ 2 hours
3. 3

   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.

Availability & pricing

4 tour options available. Pick your exact date & check live availability on the booking page.

Good to know

• 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

Cancellation policy

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