• Discover Arezzo, a true Tuscan town rich in history and local life
• Explore Cortona, known for its charm, views, and romantic atmosphere
• Experience authentic Tuscany, away from the main tourist routes
• Enjoy a wine tasting and traditional lunch in the countryside
• Travel in comfort with a private driver, with a flexible itinerary

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 enjoy a scenic drive through the Tuscan countryside, where rolling hills, olive groves, and quiet roads lead you toward a more authentic side of the region.

Your day begins in Arezzo, a city that feels lived-in rather than visited — a place where everyday Tuscan life unfolds naturally.

Known as the birthplace of Piero della Francesca and as the setting of the beloved film Life is Beautiful, Arezzo offers a rich yet understated atmosphere. It is not shaped for tourism, and that is exactly what makes it special.

As you explore its historic center, you will walk through elegant squares, local shops, and streets where residents go about their daily routines. Churches and palaces quietly hold remarkable works of art, while antique stores and small boutiques reflect the city’s long-standing traditions.

On certain days, the city comes alive with its famous Antique Fair, filling the streets with unique objects, collectors, and a vibrant local energy.

Arezzo is not about highlights.
It is about atmosphere.

From here, the journey continues through the countryside toward Cortona, where the landscape begins to open into wide views and sunlit hills.

Perched above the Val di Chiana, Cortona welcomes you with its warm stone streets, flower-filled corners, and panoramic terraces overlooking the valley below.

As you walk through its narrow lanes, you will discover artisan shops, small cafés, and quiet corners that suddenly open into breathtaking views. The town feels intimate, romantic, and deeply connected to the surrounding landscape.

There is no rush — only the pleasure of being there.

During the day, you will stop at a local winery, often family-owned and set among the vineyards.

Wine tasting here is relaxed and genuine — where each glass reflects the land, the tradition, and the people behind it.

You will also enjoy a traditional Tuscan lunch, served in a peaceful countryside setting where simple dishes, local ingredients, and regional wines come together naturally.

A table, a view, and time to enjoy it.

Throughout the day, your experience remains flexible, allowing you to explore at your own pace and enjoy each stop without rushing.

Because Tuscany is not something to rush.

It is something to live.

At the end of your experience, relax on the drive back to Siena, taking with you the feeling of having experienced a more authentic and genuine side of Tuscany.

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

Your dedicated expert driver will accompany you throughout the journey, sharing engaging storytelling, cultural insight, and authentic local perspective — revealing the true character of each destination.

With a private driver, your tour becomes more than a visit — it becomes a personalized and enriching experience designed around you.

For a deeper 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 access to both the port and the destinations.

• We recommend sunscreen, sunglasses, and light, comfortable clothing, especially during the warmer months
• Comfortable walking shoes are recommended
• Wine tastings and lunch are not included and are paid directly at the wineries
• Please inform us of any dietary restrictions in advance
• This is a private tour, fully customizable based on your preferences