• Discover Cortona, one of Tuscany’s most romantic hilltop towns
• Explore Montepulciano, known for its elegant atmosphere and wine tradition
• Enjoy a wine tasting at a local winery, often family-owned and authentic
• Experience the Tuscan countryside, with breathtaking views and quiet roads
• 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 unfold into the open beauty of Tuscany — rolling hills, olive groves, vineyards, and cypress-lined roads stretching into the distance.

This is the Tuscany you imagine.

Your day begins in Cortona, a hilltop town set high above the Val di Chiana, where light, silence, and warm stone create a feeling that is both intimate and timeless.

As you walk through its narrow streets, you will pass small artisan shops, flower-filled corners, and quiet alleys that suddenly open into sunlit piazzas. Life here moves gently — locals chatting, cafés spilling into the streets, and the scent of coffee and fresh pastries in the air.

There is something deeply romantic about Cortona.

Step onto its panoramic terraces and look out across the valley below, where fields, vineyards, and distant hills blend into a landscape that seems to go on forever. It is the kind of place where you slow down without even realizing it.

From Cortona, the journey continues through the Tuscan countryside, where every curve in the road reveals a new view — vineyards climbing soft hills, stone farmhouses, and rows of vines stretching toward the horizon.

As you arrive in Montepulciano, the atmosphere becomes more structured and refined, yet just as authentic.

Walking through its historic streets toward Piazza Grande, you will pass elegant Renaissance buildings, small wine shops, and ancient cellars carved deep beneath the town — a world where wine has been part of daily life for centuries.

Here, you may pause for a glass of Vino Nobile di Montepulciano, enjoying the balance, depth, and character that define this historic wine.

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

Wine tasting here is relaxed and personal — not formal, not rushed — where each glass reflects not only the land, but the people and traditions behind it. Conversations flow easily, and the experience feels genuine and connected to the place.

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

A table, a view, a glass of wine — and nowhere to rush.

Throughout the day, your experience remains flexible, allowing you to follow your own rhythm — whether that means lingering longer in Cortona, enjoying more time at the winery, or simply taking in the views along the way.

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 golden light fades over the hills — leaving you with the feeling of having lived a day inside the true 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