Jesse Andrews is the visionary founder behind Italy Vacation Specialists, a luxury travel company renowned for crafting highly customized, experience-rich journeys throughout Italy. With over 20 years of hands-on leadership in the tourism industry, working as an author, guide and travel company owner, Jesse has built a brand that marries deep cultural immersion with world-class hospitality serving clients ranging from discerning individuals to global organizations.
As the travel landscape evolves, Jesse is embracing the opportunities and challenges brought by artificial intelligence. Rather than seeing AI as a disruptor, she sees it as a powerful ally in enhancing client experiences, streamlining operations, and making curated travel more dynamic, responsive, and scalable. From smart itinerary design to real-time personalization and AI-driven logistics, Jesse is positioning Italy Vacation Specialists at the cutting edge of tech-enabled, human-centered travel.
With a unique ability to balance tradition with transformation, Jesse is part of a new wave of C-suite leaders who understand that the future of business lies in blending intuition, innovation, and intelligent automation.
Read our full story on our website here: https://www.italyvacationspecialists.com/our-story.html
Company: Italy Vacation Specialists
We are thrilled to have you join us today, welcome to ValiantCEO Magazine’s exclusive interview! Let’s start off with a little introduction. Tell our readers a bit about yourself and your company.
Jesse Andrews: Thank you so much, Jerome, it’s a pleasure to be here!
My name is Jesse Andrews, and I’m the founder of Italy Vacation Specialists, a travel company I started over 20 years ago when I was living in the region of Calabria in Italy’s deep south. I first went there working as an English teacher, which was a glorified babysitting job. That didn’t last long. When I was in the town of Praia a Mare, a beautiful town in the south, I wanted to get more information out to the world about this beautiful place and so I went to the mayor of the town and asked him for a grant to create a website about the town. It was a big deal at 23 years old to ask for 5000 Euro from the city hall of a town in southern Italy when I barely spoke Italian, but they did give me the grant money to build a website and promote the town, which I did. Over the years, he told his other friends in the area what I was doing and I worked for many other towns and cities in southern Italy. During this time, I built what was one of the original blogs about Italy called ItalianVisits, but that website quickly transformed over the years into a travel website, which Italy Vacation Specialists is now.
Our goal is to offer travelers a more meaningful, personalized and informed way to experience Italy. We specialize in creating custom itineraries and small-group journeys that go far beyond the typical tourist experience – focusing on authentic encounters, immersive cultural experiences, and seamless logistics. Since we know the south of Italy so well, and working as a guide, I have worked all over the country, I have met local experts everywhere and our personal and in depth knowledge of every region is what really sets us apart.
What began as a passion for sharing the real Italy with visitors has grown into a multi-faceted operation with deep roots across the country. We own and operate our own fleet of vehicles, work closely with top local guides, chefs, historians, and artisans, and manage everything from accommodations and transportation to winery visits and private events. Our clients include everyone from couples planning honeymoons to multi-generational families and even corporate groups seeking curated incentive travel.
As the world and the travel industry continue to change, I’ve become increasingly interested in how AI and emerging technologies can help us improve efficiency without losing the human connection that makes travel transformative. It’s an exciting time to be at the intersection of tradition and innovation, especially in an industry built on storytelling, emotion, and experience.
What specific areas of your business have been most impacted by AI, and how?
Jesse Andrews: As I explained at the beginning of the interview, I first started out as a writer and a photographer building websites in Italy’s Deep South, where I wrote about town after town, village after village and listed restaurants, bars, hotels and all types of businesses. It took me weeks sometimes just to finish writing up and publishing the information I was collecting about one town and I would publish all of this information to my website.
Now, AI can go online and essentially wipe all of the information I have created over 20 years right off of my websites. I’ve built more than one and written tens of thousands of pages about Italy. Essentially, what I have done in the south can essentially be stolen by AI and when I see competitors who can barely write, who may have a grade 10 education or no education at all, be able to copy and paste what Chat GBT is coming up with about a specific location, often times it seems completely unfair and almost like it’s cheating.
While AI has brought undeniable efficiencies and exciting innovations to Italy Vacation Specialists, it hasn’t come without its challenges.
One of the most noticeable issues is the risk of depersonalization. Our business is built on authentic human experiences, matching travelers with passionate local guides, crafting meaningful moments in lesser-known villages, and responding intuitively to clients’ emotions and preferences. When you start relying too heavily on automation, you risk losing some of that nuance. AI can suggest a great restaurant, but it can’t replace the warmth of a personal recommendation from someone who’s actually dined there with their family.
We’ve also found that some AI-generated content lacks cultural depth or context, especially when it comes to promoting lesser-known regions of Italy. It might produce generic descriptions, but it doesn’t understand the soul of a place or the subtle differences between the tourists trap and a hidden gems.
Another challenge is staff adaptability. Integrating AI into our operations has meant retraining parts of our team and rethinking roles. Not everyone is comfortable with these changes right away, and we’ve had to navigate some resistance and learning curves along the way.
Finally, as more companies adopt AI-driven tools, there’s growing market noise with mass-produced itineraries and content flooding the digital space. That makes it even more important for us to maintain our point of difference: handcrafted, deeply personal travel rooted in real relationships and expertise.
So while AI has helped us grow and stay competitive, it’s also made us double down on what we do best delivering genuine, human-centered travel that no algorithm can replicate.
How are you ensuring ethical considerations are taken into account in your use of AI?
Jesse Andrews: As I’ve outlined above, my own work and perhaps decades of my time have now seemed to be eroded by AI, so ethical considerations are absolutely central to how we approach the use of AI at Italy Vacation Specialists. As a company rooted in human connection, cultural respect, and sustainability, we’re very intentional about how and where AI fits into our operations.
We also prioritize data privacy and security. We only use AI tools that are compliant with GDPR and other relevant data protection laws, and we never sell or share client data. Our clients entrust us with sensitive travel information, and safeguarding that is non-negotiable.
From a cultural standpoint, we’re especially careful about using AI to generate content or recommendations. We’ve seen how AI can oversimplify or misrepresent cultural traditions or local customs, so any AI-generated suggestions are always vetted by a human – typically a local expert before they’re passed on to clients. We believe strongly in cultural integrity, and that means making sure the stories we tell and the experiences we offer are authentic and respectful.
Finally, we’re investing in education and training for our team so they understand the ethical implications of AI – not just how to use it, but how to question it, challenge it, and apply it responsibly.
To me, using AI ethically isn’t just about compliance – it’s about aligning with our company’s values of honesty, personalization, and deep respect for the places and people we work with. That’s what makes our brand meaningful, and it’s what guides every decision we make, tech included.
What advice would you give to other CEOs looking to integrate AI into their business?
Jesse Andrews: Personally, I think it’s foolish for companies and CEO’s not to be looking at how AI can streamline their operations and provide critical data. I think it’s fundamental to leverage what we can from AI and use it to hopefully improve our businesses and better manage our own time.
My advice to other CEOs looking to integrate AI into their business is this: don’t start with the technology, start with your values and your vision.
AI is a powerful tool, but it’s not a magic solution. Before diving into platforms and systems, take the time to ask: What do we want to enhance? What do we want to protect? And what makes our business human, irreplaceable, and valuable to our clients? Your answers to those questions should guide your approach to AI, not the other way around.
Second, involve your team early and often. Change can feel threatening, especially in industries that rely on craftsmanship, creativity, or close client relationships. Frame AI as an amplifier, not a replacement – something that removes friction and frees up your people to focus on what they do best.
Also, don’t underestimate the importance of vetting your tools carefully. Not all AI is created equal. Prioritize platforms that are transparent, respect data privacy, and can be tailored to your business’s unique needs. Avoid being seduced by the flashiest tech if it doesn’t serve your clients or your brand.
And finally, stay curious, but grounded. AI is evolving fast, and you don’t have to adopt everything at once. Start small, measure the impact, and scale what works. The smartest CEOs I know are the ones who see AI not as a trend to chase, but as a strategic asset to harness with purpose, responsibility, and vision.
How do you see AI evolving in your industry over the next 5 years?
Jesse Andrews: Over the next five years, I believe that AI will completely reshape the travel industry, not by replacing human touch, but by redefining how personalization, planning, and service are delivered.
We’re already seeing AI enhance the way travelers discover destinations, with smarter search tools, dynamic pricing, and instant itinerary generation. But going forward, I see AI becoming far more predictive and proactive, anticipating a traveler’s needs before they even express them. Think of AI-driven platforms that adjust plans in real time based on weather, crowds, or personal preferences gathered over years of travel history.
In the luxury and bespoke travel space, where I operate, AI will play a major role behind the scenes: helping advisors and tour operators like us optimize logistics, identify emerging trends, and reduce friction while still allowing us to curate journeys with human insight and emotion. The challenge will be using AI to enhance creativity, not suppress it.
On the operational side, AI will transform customer support, supplier communications, and even sustainability practices. It will enable smarter resource allocation, greener routing, and better tracking of the environmental impact of trips – something increasingly important to travelers and companies alike.
That said, as AI becomes more integrated, trust and transparency will become even more important. Clients will want to know where AI is being used, how their data is being handled, and whether what they’re seeing is authentic. So businesses that embrace AI ethically and responsibly without losing sight of human connection will be the ones that thrive.
In short, AI is going to make travel smarter, more fluid, and more accessible but the soul of great travel will always come from human stories, relationships, and the unexpected magic that no algorithm can predict. And all the while, while AI will certainly play a big part of how the travel industry evolves, I still believe that talking to experts in any field, being able to have a real conversation with someone who is not a robot, being able to make eye-contact or connect with another human being over coffee, those human to human connections will become ever more valuable as AI continues to evolve. I just happen to think that AI can help in many ways in forging even greater understanding about each other and a variety of topics, so I’m hoping it will be a win-win for all if we manage it correctly.
