Guest blog post from Felicity Leo

Why human connection still matters

The reality is, Artificial Intelligence is built into our daily lives. From writing emails and fixing typos to streamlining everyday tasks, AI is already everywhere. AI-powered trip planning tools like ChatGPT and booking apps have made it easier than ever to find cheap flights, optimize schedules, and organize travel details.

But while these tools are super impressive, there’s one thing they can’t replicate: the irreplaceable value of human connection and personalized service in luxury travel planning!

Think of AI as a sleek, high-tech car—it might get you from point A to B quickly, but only a real person can steer you toward the moments that truly matter.

Travel That Feels Right

Sure, AI can suggest trending destinations, compare hotel rates, and build itineraries. But it can’t match the depth of understanding that comes from working with a trusted travel consultant, like Anna at Olegana Travel Boutique.

Anna transforms your travel into a tailor-made, seamless vacation filled with meaningful moments—not just scheduled stops.

Experiences Beyond the Itinerary

Luxury Travelers are craving more than just passport stamps—they want immersive cultural experiences and stories worth telling. During Anna’s winter group trip to Venice, Italy, she brought the magic of Carnevale to life in December—off-season, intimate, and unforgettable.

A truly festive moment, rooted in deep cultural knowledge and local access. That’s not something AI could plan.

Recently, when I visited Santorini, I was a bit overwhelmed by AI-generated travel tips, all focused on capturing the “perfect” photo of Oia’s blue domes. But it was the quieter moments—the hidden boutique hotel, the guide who shared local legends—that made my vacation more enjoyable and effortless.

Where is AI When Things Go Wrong?

In the middle of your dream vacation, if things go sideways, that’s when the difference between artificial support and real human partnership becomes crystal clear.

AI doesn’t troubleshoot in real time.

That’s the value of a trusted travel advisor—someone who doesn’t just plan your trip, but steps in and advocates for you when it matters most. Whether it’s a canceled flight, a check-in mix-up, or a spontaneous detour to a local vineyard, your advisor picks up the phone, talks to the right people, and pivots your itinerary, so you can continue to create magical moments.

Whether you’re planning a solo trip or a family vacation, go beyond search engines and AI-generated itineraries. Connect with Anna Fishman today to start planning a journey that reflects your style, pace, and story, not algorithms.