Brunello and Montepulciano Wine Tour from Cortona

Experience the Heart of Tuscany’s Wine Country Without the Hassle

If you’re dreaming of Tuscany’s legendary wines—from Brunello di Montalcino to Vino Nobile di Montepulciano—this guided wine tour from Cortona offers a relaxed, informative peek into the region’s vinicultural treasures. For around $390 per person, you get about eight hours of scenic driving, tastings, and cultural stops, with pickup included. Your guides—who are passionate and knowledgeable—will handle the logistics, so you can focus on savoring the wines and the views.

Two things we love about this experience are the chance to visit two different wineries, each with its own character and story, and the opportunity to stop in Pienza, the charming “pearl” of Val d’Orcia, for a cheese tasting and a walk through its historic streets. Plus, the included lunch at a historic, underground cellar makes the day feel special—not just a tasting but a full immersion into Tuscan culinary traditions.

A possible consideration? The group size is limited to 8 travelers, which keeps things intimate but might fill up quickly. Also, since the tastings are part of the tour, if you’re a very seasoned wine connoisseur looking for a deep dive, you might find it more curated than comprehensive. For most, however, this tour strikes a good balance of education, flavor, and scenic beauty.

This experience works best for travelers who want to leave the driving behind and enjoy authentic, small-scale wineries, combined with a taste of local culture. It’s particularly suited for those who appreciate guided storytelling, picturesque countryside, and good food paired with wine.

This experience made our article of 15 Best Wine Tours In Arezzo.

Key Points

• All-inclusive experience with transportation, tastings, and lunch.
• Visit two distinct wineries with personalized tours and tastings.
• Stop in Pienza for a stroll and cheese tasting—perfect for a quick cultural fix.
• Scenic drives through Val d’Orcia, one of Tuscany’s most iconic landscapes.
• Small group size ensures a more intimate, engaging experience.
• Guides are highly praised for their knowledge and friendliness.

A Closer Look at the Brunello and Montepulciano Wine Tour

When we think of Tuscany, images of rolling hills, cypress trees, and bottles of world-famous wine come to mind. This tour takes you straight into that picture, without the hassle of navigating unfamiliar rural roads or worrying about parking. Instead, your guide, often described as friendly and well-informed, will handle the driving, so you can relax and focus on the experience.

The Itinerary: What You’ll Actually Do

The day kicks off early, with a pickup at 8:30 am, typically from your hotel or nearby accommodation. This is ideal for travelers staying in or near Cortona, who want a full day of exploring. The first stop is Montalcino, home to the coveted Brunello di Montalcino. Here, you’ll visit a boutique winery and meet the owners, giving you a glimpse of the passion and tradition behind the wine. Expect to sample Brunello, Riserva, and Supertuscan, offering a good range of what makes this region’s reds so special.

Many reviews highlight how informative and friendly the guides are, often sharing the secrets of the wine-making process and regional history. Sandra E. notes, “Our driver was wonderful, stopping at several locations for pictures and information.” That personal touch can turn a simple tasting into a memorable lesson.

Next, you’ll continue to Val d’Orcia, one of Tuscany’s most picturesque areas. The second winery, one of the oldest in the region, offers another tasting session with more Brunello and an even more scenic drive through rolling hills and cypress-lined roads. Expect to hear stories about the history of the vineyard and region—many of which guides like Michele or Niccolo are eager to share, making the experience more than just sipping wine.

The Cultural and Gastronomic Highlights

A charming stop in Pienza gives you about an hour to walk through its narrow streets, admire its Renaissance architecture, and, of course, savor local pecorino cheese. Several travelers, including Sheri T., mention that the cheese tasting was a highlight: “The wineries were gorgeous and super friendly,” she says, “but the cheese stop was a perfect addition to the day.”

Finally, the tour concludes with a pairing lunch in Montepulciano, held in an atmospheric underground cellar. This is a true highlight—an opportunity to taste Vino Nobile di Montepulciano paired with local specialties in a historic setting. The lunch is described as fabulous and well-paced, giving you time to relax and soak in the atmosphere.

The Value of This Experience

Given the cost—around $390—this tour offers good value for those wanting a comprehensive, guided day that includes transportation, tastings, a scenic drive, cultural stops, and a hearty Tuscan lunch. Reviews consistently praise the quality of the wines, the friendliness of the guides, and the stunning landscapes. Many reviewers remark that they learned a lot, especially about the specific wines and regional history, which enhances the tasting experience.

The Challenges and Limitations

While most reviews are glowing, a few mention that the wine tastings are good but not necessarily “exceptional,” or that the driver was not particularly wine-savvy. Keep in mind that this is a guided tour focused on a broad experience, so if you’re seeking an in-depth, vineyard-by-vineyard exploration or very specific wine education, you might find this a bit surface-level. The group size, although small, means some interaction will be limited, and the pace might not suit travelers looking for a very leisurely or customized experience.

Who Should Book This Tour?

This tour is ideal for wine lovers who appreciate small-group experiences, scenic drives, and cultural touches like cheese tasting and town strolls. It suits travelers who want a taste of Tuscany’s top wines without the stress of driving and are happy with an itinerary that includes highlight visits and a hearty meal. It’s especially good for those new to the region or wine enthusiasts wanting a well-rounded, authentic day trip.

The Bottom Line

This wine tour from Cortona captures the essence of Tuscany’s renowned winemaking traditions in a way that’s accessible and enjoyable. The combination of guided visits, scenic drives, and culinary delights makes it a well-rounded experience.

Most travelers rave about the knowledgeable guides, stunning landscapes, and delicious wines and food. The experience is relaxed but packed with memorable moments—perfect for those who want to learn, taste, and enjoy without the worry of planning every detail themselves.

It’s a particularly strong choice for small groups who value personal attention and authentic ambiance, making it a worthwhile splurge for your Tuscan adventure.

Frequently Asked Questions

How long is the tour?
The tour lasts approximately 8 hours, from pickup at 8:30 am to drop-off later in the day.

Is transportation included?
Yes, a luxury, air-conditioned vehicle with wifi is provided for the entire day.

What is the group size?
The tour is limited to a maximum of 8 travelers, ensuring a more intimate experience.

Are the wine tastings in the wineries included in the price?
Yes, both winery visits include tastings, and the pairing lunch at Montepulciano is also included.

Can I cancel if my plans change?
Yes, you can cancel free of charge up to 24 hours in advance for a full refund.

Is this tour suitable for children or service animals?
Service animals are allowed, and most travelers can participate. However, since the experience involves tastings, it’s best suited for adults.

Do I need to prepare anything in advance?
Just bring your curiosity and a sense of adventure! The guides will handle the rest, and confirmation will be provided upon booking.

What should I wear or bring?
Comfortable shoes for walking in Pienza and possibly uneven winery floors, and a camera for the scenic views. Water and any personal essentials are also recommended.

Embark on this guided journey through Tuscany’s iconic wine country—an experience that promises beautiful scenery, rich flavors, and stories worth sharing long after the last sip.