• Florence - Experience the pinnacle of Tuscan elegance with a private tour through the UNESCO-listed Val d’Orcia, where every turn of the landscape resembles a living painting. This exclusive adventure begins with a personal pick-up from your accommodation in Florence by your private chauffeur, ready to transport you in a luxury vehicle. Relax in the comfort of your plush seat and watch as the scenery shifts from urban charm to rolling hills, vineyards, and iconic cypress-lined roads.

This enchanting drive, lasting approximately two hours, provides a peaceful transition into the heart of Tuscany. As you journey through the countryside, your driver will attend to every detail, offering insights or simply ensuring a quiet, seamless trip tailored to your preferences. Val d’Orcia awaits with its postcard-perfect vistas, medieval hill towns, and timeless ambiance, setting the stage for a day of indulgence, discovery, and authentic Tuscan beauty.

• Montalcino - After a picturesque drive through some of Tuscany’s most captivating landscapes, your first stop invites you to slow down and enjoy the charm of Montalcino, the birthplace of the renowned Brunello wine. Nestled among rolling vineyards and oak-covered hills, this medieval treasure 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 leisure. Stroll through winding cobblestone streets, browse artisanal wine shops, and soak in the timeless atmosphere that defines Montalcino. As you ascend the town, the 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.

• Cappella della 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. Request your driver to take 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.
• Terrapille Farmhouse - 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.

• 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.

• 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.

• 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.

• 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

Embark on a private tour through the heart of Tuscany’s Val d’Orcia, accompanied by your personal driver. Sit back and enjoy the scenic journey through rolling hills, roads lined with cypress trees, and picturesque villages. Your adventure begins in Montalcino, renowned for its world-famous Brunello wine. Wander through its cobblestone streets, explore wine shops, and admire Romanesque churches. Next, head to Pienza, a Renaissance treasure perched on a hilltop, offering breathtaking views of the valley. Redesigned by Pope Pius II, it is celebrated for its harmony, beauty, and delectable Pecorino cheese.

During your journey, pause at the iconic Chapel of the Madonna di Vitaleta, one of Tuscany’s most photographed sites, beautifully framed by cypress trees in a memorable setting. Then, visit the nearby fields featured in the movie Gladiator, where Russell Crowe’s character strolls through golden wheat towards his home. Conclude your day in Montepulciano, known for its Vino Nobile and sophisticated Renaissance allure. Experience the essence of Tuscany through its landscapes, flavors, and timeless beauty.

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