Anna Maria Madaffari Interview
In the heart of Tuscany, where rolling vineyards meet centuries of tradition, Anna Maria Madaffari, founder of Cooltours, has redefined what it means to explore wine country. Her company focuses on boutique, sustainable, and family-style wineries, offering travelers authentic, intimate encounters rather than commercialized tours. In this interview with The Worlds Times, Anna shares how she balances authenticity with guest expectations, adapts to the evolving tourism landscape, and builds a brand rooted in storytelling, culture, and genuine human connection.
Selecting Authentic Partners
We started the interview by asking, “Cooltours emphasizes boutique, sustainable, family-style wineries and authentic experiences. How do you select the wineries and partners you work with, and how do you balance authenticity with guest expectations?”
Anna Maria Madaffari replied, “Anna might explain that the process always begins with personal visits. She or a member of her team spends time at the winery to experience not just the wine, but the philosophy behind it, the family history, and the way the land is cultivated. Guests often imagine Tuscany as a polished postcard, but she believes authenticity comes from showing them the working side of wine culture. To balance this with guest expectations, she sets clear communication before the tour so people know if they are walking into a rustic family farm or a more refined estate. That way, when visitors arrive, they can appreciate the winery for what it truly is, rather than measuring it against preconceived notions.”
Wearing Many Hats
The Worlds Times: You’re listed as driver-guide, tour leader, and Level 3 sommelier. How do those multiple roles shape your business decisions and the guest experience?
Anna Maria Madaffari replied, “Anna could describe how wearing these three hats keeps her connected to every aspect of her business. As a sommelier, she brings depth and credibility to tastings, helping guests understand varietals, vintages, and terroir in a way that is approachable and engaging. As a driver and tour leader, she experiences firsthand the logistics of each journey the pacing, the comfort, the atmosphere in the van, and the mood of the group. This direct involvement allows her to adjust quickly and refine the details that make a tour seamless. Her active role ensures that decisions are not made from an office but from the road, informed by the real experiences of her guests.”
Adapting to Change
The Worlds Times: Tourism has shifted with new customer expectations, sustainability concerns, and the impact of technology. How has Cooltours adapted to these changes, and where do you see the biggest challenges ahead?
Anna Maria Madaffari replied, “She might reflect on how travelers today seek something more meaningful than a quick photo opportunity. Many want to support small businesses, reduce their footprint, and feel part of the place they are visiting. Cooltours has responded by keeping groups small, prioritizing wineries with sustainable practices, and offering itineraries that highlight genuine cultural connections. At the same time, technology has changed how clients discover and book tours, so maintaining a strong online presence and responding quickly to feedback has become essential. The challenges ahead, she could say, lie in balancing growth with intimacy. As Tuscany attracts more visitors, the risk is that the very authenticity people come for may be diluted. Preserving that balance will remain her greatest focus.”
Lessons from the Road
The Worlds Times: Could you walk us through a particularly memorable or challenging tour you organized, what made it special, what unexpected issues came up, and what you learned from it?
Anna Maria Madaffari replied, “Anna might recall a day when heavy rain forced a sudden change of plans. The winery they were scheduled to visit had accessibility issues in bad weather, so she improvised by contacting a small estate nearby where she had personal connections. The group ended up having a home-cooked lunch with the winemaker’s family, something not planned but incredibly memorable for everyone involved. The lesson, she could say, was the importance of flexibility and trust in local relationships. While guests never saw the stress behind the scenes, what they experienced was a warm, authentic moment that turned a potential problem into the highlight of their trip.”
The Story of Cooltours
Lastly we asked, “Brand identity and storytelling are essential in travel and wine tours. How do you brand Cooltours and how do you tell its story to guests before, during, and after the tour?”
“She might explain that Cooltours is not just a service but a philosophy of travel: small groups, real connections, and the belief that wine is a gateway into culture. That story is told before the tour through the website and her communications with clients, where she sets the tone of intimacy and authenticity. During the tour, the storytelling continues through anecdotes, historical context, and personal introductions to winemakers, so guests feel they are part of a narrative rather than just consumers. After the experience, she encourages people to stay connected, to share their memories, and to bring a piece of Tuscany home with them. In this way, Cooltours becomes not just a one-day excursion but part of a larger personal journey.” Anna Maria Madaffari concluded
Connect with Anna Maria Madaffari on LinkedIn
For more information visit Cooltours
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