AI Can Plan Your Vacation. Here’s Why Affluent Travelers Still Call Me.

I use artificial intelligence every day.

I use it to draft, research, organize, and brainstorm. It saves me real time. I’m not going to pretend otherwise, and I’m not threatened by it. But I’m not going to let it design my clients’ vacations, either.

Here’s why AI is useful and where it falls short of expectations.

The itinerary that looked right.

A prospective client reached out recently about a European trip. She’d already built an itinerary with ChatGPT and didn’t want to start over — she wanted me to review it and build from there. Fair enough.

At first glance, it looked solid. The cities made sense. Several hotel suggestions were good. AI had done exactly what AI does well: gathered an enormous amount of information very quickly.

Then I started working through it, and the gaps became clear.

Some recommendations didn’t fit her travel style at all. The pacing was wrong for someone who likes to slow down and breathe. And a few of the transfer times weren’t just optimistic — they were impossible. If she’d followed that itinerary, she would have spent her vacation rushing, not traveling.

ChatGPT didn’t fail. It did exactly what it was built to do. The problem is that it didn’t know her.

It didn’t know how she moves through a destination, how much downtime she needs, or which experiences she’d still be talking about five years from now. It knew the destination. It didn’t know the traveler it was asked to match the experience to. That’s the difference between generating an itinerary and designing a journey.

Think of AI as an exceptionally well-read intern. Fast, capable, genuinely useful — and still in need of someone with experience to review the work and catch what doesn’t fit.

Information isn’t expertise.

AI answers questions like:

• What hotels are available?
• How long is the train ride?
• What are the top-rated restaurants?
• What’s the weather like in September?

Useful. Worth knowing. Luxury travel runs on a different set of questions entirely.

Is Lake Como actually the right fit, or would Lake Orta better match this client’s temperament? Will changing hotels every other night feel adventurous or exhausting? Is that Michelin-starred reservation worth pursuing, or would a family-run trattoria create the memory that outlasts the trip? Should they add a day in Tuscany and skip one in Florence?

The answers to those questions aren’t search results as much as they are judgment calls. And they come from experience, not a search engine.

The problem that never became a problem.

One of my clients was traveling through Italy, scheduled to take the train from Modena to Venice. Two days before departure, my Italian destination partner reached out: the train had been canceled.

Before my client knew there was a problem, we’d already arranged an alternative.

He never stood in a crowded station wondering what happened. He never scrambled. He just got to Venice. And our arrival assistant was waiting for him on the platform. AI could have helped him search for options after he arrived at the station. My team solved it before he packed his bag.

Technology flags the problem. People fix it.

2 a.m. in New York.

A client was flying first class to Paris via a New York connection. At 2:00 in the morning, my flight-monitoring software alerted me to a significant delay on their first leg. If nothing changed, they’d miss their international connection and lose a full day of a vacation they’d invested serious money in.

I contacted my air desk’s emergency team immediately. We protected seats on another flight before most travelers even knew there was an issue. Two hours before my clients left for the airport, I texted them. Explained the situation. Told them what we’d done. Told them they were taken care of.

They walked into the airport already knowing everything had been handled.Technology told me something was wrong, but it was people who made it right.

The upgrade nobody asked for.

Not every story is about fixing something — sometimes it’s about anticipating what matters.

A client stayed at the same luxury London hotel before and after a European trip. Because I’ve spent years building a relationship with that property’s leadership, the staff remembered them when they returned. Waiting for them was an upgrade to an Executive Suite and a personal welcome from the General Manager.

I never asked for either. The hotel simply wanted to recognize valued guests from a trusted partner.

That moment doesn’t appear in any algorithm. It’s built through years of showing up, following through, and sending the right people to the right places.

What I’d actually recommend.

Use AI. I really mean that. Ask it questions, explore ideas, let it help you build a rough framework for a trip. It’s a genuinely useful starting point.

Then bring what you’ve learned to someone whose job is to know when the information is wrong, when the pacing is off, when the “top-rated” option isn’t right for you, and what to do at 2 a.m. when things fall apart.

AI generates answers. A luxury travel advisor is accountable for the outcome.

When you’re investing tens of thousands of dollars in an experience, that distinction is everything.

---

Shannon Lamarche is the founder of Premiere Luxury Travel and a Virtuoso advisor specializing in custom European journeys, African safaris, and small-ship and river cruising. She uses AI as a business tool and relies on 20+ years of experience, trusted global partnerships, and firsthand destination knowledge to ensure her clients’ trips go the way they’re supposed to.