• Explore two of Tuscany’s most iconic destinations, Pienza and Montalcino
• Experience the world of Brunello di Montalcino, one of Italy’s most prestigious wines
• Taste local specialties, including the famous Pecorino cheese of Pienza
• Enjoy the breathtaking landscapes of the Val d’Orcia, one of Italy’s most celebrated regions
• Travel in comfort with a private driver, with a flexible itinerary tailored to your pace

We offer a private Mercedes Minivan and an English-speaking driver, ensuring a smooth and comfortable experience throughout the day. Your driver will be waiting in your hotel lobby or at a convenient meeting point, holding a sign with your name.

Leave the city of Siena behind and watch the landscape slowly soften into the timeless beauty of the Val d’Orcia, where winding roads, cypress trees, vineyards, and golden fields create the Tuscany of the imagination.

This is the kind of countryside that invites you to slow down.

Your day unfolds in Pienza, a hilltop town gently set above the valley, where light, space, and silence create a rare sense of balance.

As you walk through its stone streets, you will discover elegant squares, panoramic terraces, and quiet corners overlooking the countryside — views that seem to stretch endlessly into the horizon.

Small local shops invite you to step inside, where you can discover Pecorino cheese — the pride of the region — in its many forms: fresh, aged, and often paired with honey or local specialties.

It is simple, authentic, and deeply connected to the land.

Leaving Pienza behind, the road begins to move through open countryside, where vineyards gradually take over the landscape and lead you toward Montalcino.

Perched high above the surrounding hills, Montalcino carries a deeper, more contemplative atmosphere — a place where time, tradition, and craftsmanship shape everyday life.

Here, wine is not just produced.
It is lived.

Walking through the town, you will find quiet streets, small wine shops, and unexpected viewpoints opening over endless vineyards and rolling hills.

It is easy to understand why Brunello di Montalcino has become one of the most admired wines in the world — everything here reflects patience, care, and character.

During the day, you may choose to stop at a local winery for a tasting (optional), where wine is shared with authenticity and pride, often accompanied by simple regional products.

You may also choose to enjoy a traditional Tuscan lunch (optional), where seasonal ingredients, local recipes, and regional wines come together in a relaxed countryside setting.

These are the moments that stay with you.

Throughout the day, your experience remains flexible, allowing you to follow your own rhythm — whether that means lingering over a view, spending more time at a winery, or simply enjoying the quiet beauty of the landscape.

Because Tuscany is not just something to visit.

It is something to feel.

At the end of your experience, relax on the drive back to Siena, as the hills slowly fade behind you — leaving you with the lasting impression of a day lived in the true heart of Tuscany.

Elevate your day with a customized winery selection, tailored to your preferences for wine style, setting, and atmosphere.

Your English-speaking driver will accompany you throughout the journey, ensuring a smooth, relaxed, and flexible experience as you explore Tuscany at your own pace.

For a more personalized experience, additional stops or extended time at wineries can be arranged upon request.

For groups of 9–24 guests, multiple minivans will be arranged to ensure maximum comfort and seamless travel throughout the day.

• We recommend sunscreen, sunglasses, and light, comfortable clothing, especially during warmer months
• Comfortable walking shoes are recommended, as visits include walking in hilltop towns and wineries
• Wine tastings and lunch are not included and are paid directly on site
• Please inform us of any dietary restrictions in advance
• This is a private and fully customizable experience, tailored to your preferences