Tuscany – A Journey Into the Heart of Italy
I created this tour for a couple staying in one of our villas in Florence. They had just one full day available and dreamed of seeing Montepulciano, Montalcino, and Pienza—but without the stress of navigating the countryside themselves. I wanted to offer them a day that was relaxing, scenic, and unforgettable. That’s how this itinerary was born, and it quickly became one of our most requested experiences.
I consider myself lucky—I live in one of the most beautiful countries in the world. Thanks to my job, I travel to Tuscany at least ten times a year. I personally oversee the villas we manage, connect with local winemakers, trusted drivers, and the restaurants we love to recommend to our guests from all over the world. And every time I get the chance, I can’t resist—I jump in the car and head straight to Val d’Orcia.
Why? Because this is the most scenic part of Tuscany. Picture-perfect landscapes, rolling hills, winding cypress-lined roads, and villages that feel suspended in time.
Montepulciano, Pienza, and Montalcino
Since 2004, Val d’Orcia has been listed as a UNESCO World Heritage Site. Located in southern Tuscany, it’s home to some of the region’s most enchanting medieval towns: Montepulciano, Pienza, and Montalcino. Each one has a distinct soul, rich traditions, and flavors that linger long after your visit ends.
That’s why we created the “Florence: Montepulciano, Pienza & Montalcino Private Trip” — a full-day experience that blends history, beauty, and taste. It’s ideal for American travelers seeking to explore authentic Tuscany with the comfort of a private English-speaking local driver, like our trusted Fabrizio or one of his passionate colleagues.
THE TOUR
Tuscany Tour From Florence – or Anywhere
The tour can start from Florence, Rome, or even other cities upon request.
Your driver will pick you up in a luxury Mercedes sedan or minivan, air-conditioned and ultra-comfortable. To make the most of your day, we recommend an early start—around 7:45 or 8:00 AM.
First Stop: Montepulciano
The journey begins in Montepulciano, perched between the Val di Chiana and Val d’Orcia. Famous for its Vino Nobile, this medieval town invites you to stroll cobbled streets, admire Renaissance palaces, and explore ancient wine cellars that lie beneath the city.
Fabrizio will walk you through the ideal route, bringing you to Piazza Grande, the town’s heart, while sharing stories of noble families and their centuries-old winemaking heritage.
Second Stop: Pienza
A short scenic drive brings you to Pienza, a Renaissance jewel redesigned by Pope Pius II. This charming town is known not only for its architectural harmony and sweeping views of the valley, but also for its delicious aged pecorino cheese, sold in fragrant little shops that line its romantic streets.
Stroll along Via del Bacio (“Kiss Street”) or Via dell’Amore (“Love Street”), and you’ll understand why so many travelers fall head over heels for this place.
Third Stop: Lunch at a Winery
For lunch, you can choose between a vineyard with stunning views or a local trattoria in the heart of town.
We recommend enjoying a traditional Tuscan meal at a family-run winery in Montalcino—with handmade pici pasta, cinta senese pork, and local crostini, paired with none other than a glass (or two) of Brunello di Montalcino.
Please note: lunch is not included in the tour price, but reservations can be made in advance.
Final Stop: Montalcino
In the afternoon, you’ll arrive in Montalcino, a peaceful hilltop village famed for its wine, charm, and the medieval Rocca fortress, which still watches over the valley.
Here, you’ll have time to explore the town, enjoy breathtaking views, and visit some of the best Brunello wine shops — ideal for tastings or shipping bottles back home.
Return
Your driver will take you back to your accommodation in the late afternoon—leaving you with lasting memories, unforgettable photos, and the taste of Tuscany in your heart.
MY POINT OF VIEW
Whether you’re visiting Tuscany for the first time or returning to soak in more of its magic, this private day trip is the perfect way to discover one of the most fascinating places in Italy.
By traveling with a local English-speaking driver, you avoid the stress of planning and driving, and instead enjoy a relaxed, immersive experience. The drive from Florence to Montepulciano takes about 1 hour and 45 minutes, followed by short and scenic rides between towns.
