Why AI Doesn’t Replace a Travel Advisor… It Replaces an Amateur

Let me explain it the way I think about it.

I grew up just outside New York City; my dad’s side is 100% Italian. Cooking wasn’t a hobby, it was part of daily life. We grew vegetables. We cooked every night. We spent decades around some of the world’s best restaurants.

Then I spent twenty years in finance in New York City, where taking clients out meant experiencing the city’s best restaurants, which only sharpened my understanding of food, service, and what is truly worth recommending.

Now, as a travel advisor, I’ve been to Italy repeatedly and design experiences around food, culture, and experiences. So if I recommend a restaurant in New York City, that recommendation carries weight. Not because it’s my opinion. Because it’s informed.

What’s the value of an unsubstantiated review? Are you more inclined to trust Anthony Bourdain… or a handle you’ve never heard of?

AI Is Built on That Same Noise

AI tools are powerful. But they don’t have taste. They don’t have experience. They don’t have relationships. They aggregate.

They don’t know:

• If a hotel’s service has slipped recently
• If a leadership change altered the culture
• Which “luxury” property photographs beautifully but disappoints in person
• Which tour guide elevates an experience and which one diminishes it

Because they haven’t been. And if you haven’t been, you can’t measure the experience.

What AI Is Good For

To be clear, I actually encourage clients to use AI.

Ask for:

• A rough 8-day framework
• A list of top experiences
• A starting point

It’s a far better way to begin than opening 40 browser tabs. But that’s all it is. A starting point. Use AI to sanity check flights, routing, and timing to see what might work before we sit down. That’s closer to real research.

Just understand that what most people call ‘research’ is often just visiting a series of hotel websites, which are marketing platforms designed to convince everyone they’re perfect for everyone.

The Missing Piece: Knowing Your Lane

Here’s the part most people miss. No matter how intelligent or accomplished we are, we only know what we know. I spent 20 years on Wall Street, and by most assumptions, I should manage my own money. I don’t. Not because I couldn’t learn it, but because I didn’t live in that segment of the business. My background is in risk arbitrage and equity derivatives, understanding volatility and the probability of outcomes. That’s my lane. Managing wealth, day in and day out, is someone else’s, and I have enough respect for that discipline to know the difference.

Same idea at home. My brother-in-law is an attending oncologist. If we called him about our son, he wouldn’t pretend to have the answer. He’d say, “I’m not a pediatrician. That’s not my lane.” That’s what real expertise sounds like. It doesn’t blur lines; it respects them.

And that’s really the point. A specialist will always outperform a generalist in their domain, and a generalist will outperform an amateur. The problem is that most travelers are unknowingly relying on the latter, and calling it research, even when the inputs themselves were never informed to begin with.

Travel is my lane. It’s what I do personally and professionally, every day. And before doing this professionally, even with extensive travel experience, I had no idea how many doors simply didn’t exist until I was on the inside.

Relationships, access, context, that’s what changes everything, and it’s what most travelers don’t realize they’re missing.