How to Make AI Automation Work for Luxury Travel

You’ve probably tried it by now. You open ChatGPT, type something like “write an email to a client about their trip,” and the response appears fine. Polished, even. But also a little lifeless.

That’s the thing about AI. It’s fast and capable, but when left to its own devices, it defaults to corporate-speak. And in luxury travel, where relationships matter more than rates, that doesn’t cut it.

Dr. Jill Schiefelbein gets it. During our recent AI Exploration webinar series, she walked through why automation often feels cold and what we can do about it. Her take is that AI isn’t the problem. It’s how we’re asking it to help.

If you’ve been hesitant to lean into automation because you’re worried it’ll strip the personal touch from your business, read on to learn how you can keep the human element.

The Touchpoints That Actually Matter

Before we get into the how, let’s talk about the why. Because automation for its own sake is just noise.

Jill broke down what makes communication with clients stick. Higher sales, better retention, more referrals. The patterns are clear:

Personalization wins. When something feels tailored to the individual, not just their segment, people respond. They book. They come back. They tell their friends.

Choice matters. Give clients optionality. Let them steer the conversation, even a little. That sense of agency builds trust.

Consistency is hard without help. You want to stay top of mind. You want every touchpoint to feel intentional. But doing that manually, at scale, with everything else on your plate? It’s not realistic.

That’s where AI comes in. Not to replace you, but to free you up for the parts of your job that actually require you.

Better Prompts, Better Outputs

You can’t just tell AI what you want and expect magic. It needs context. Direction. The kind of detail you’d give an intern on day one.

Jill used that exact framing: “This is how I would instruct an entry-level employee on the very first day of their job who knows nothing about me and nothing about my business and nothing about my clients.”

When you think of it that way, the whole thing clicks.

So what goes into a good prompt? Jill laid out the anatomy:

Who is it acting as? Are you asking AI to be a knowledgeable advisor, a friendly concierge, or a behind-the-scenes planner?

What’s the format? Email? Itinerary summary? Social post?

What are the specifics? Trip dates, destinations, and client preferences. The more you include, the less guesswork AI has to do.

What’s the goal? Are you confirming details, upselling an experience, or just checking in?

Who’s it for? A first-time client? A repeat traveler who books the same villa every year? Tone shifts based on the audience.

What’s your voice? This is where brand comes in. Warm, professional, a little cheeky. You get to set the tone.

Any must-includes? Links, specific amenities, deadlines. Call them out upfront.

The difference between a vague prompt and a detailed one isn’t subtle. It’s the difference between something you can use and something you have to rewrite from scratch.

Start With the Experience, Not the Tool

One of the smartest things Jill said? Stop asking “What’s the best tool?” That’s the wrong entry point.

Instead, ask yourself:

• What experience do I want to create for this client?
• What result am I trying to get?
• What would actually help me get there?

The tool comes last. Because once you know what you’re solving for, finding the right solution is easier. Maybe it’s an AI assistant that drafts follow-up emails. Maybe it’s a workflow automation that sends trip reminders. Maybe it’s just a better prompt template you reuse.

But it starts with clarity about what you’re trying to do and why it matters to your client.

Putting It Into Practice

Let’s say you want to send a post-trip follow-up. You could ask the AI agent to “write a thank-you email,” and you’ll get a generic response. Or you could try this:

“Act as a luxury travel advisor. Write a warm, professional follow-up email to a client who just returned from a two-week trip to Italy. They stayed at a villa in Tuscany and took a private cooking class in Florence, which they mentioned loving. Thank them for their business, ask if they’d share feedback, and let them know you’re already thinking about their next trip. Keep it conversational and under 150 words.”

See the difference? You’ve given your AI agent enough to work with. Now it can actually sound like you.

What This Means for Your Business

Automation isn’t about cutting corners. It’s about creating space. Space to focus on the high-touch moments that matter. Space to build relationships, not just itineraries.

When you get the inputs right, AI becomes a tool that amplifies your voice rather than replaces it. You still bring the expertise, the intuition, the personal connection. AI just helps you scale it without losing what makes you, you.

And in an industry built on trust and experience, that balance is everything.

If you want to go deeper on this, Jill’s work at The Dynamic Communicator is worth exploring. She’s spent years studying what makes communication work, and her approach to humanizing automation is grounded in real strategy, not hype.

We’re continuing this conversation in our AI Exploration series. If you missed this session and want to catch the replay, check it out here.

Where to Go From Here

Start small. Pick one part of your workflow that feels repetitive. A welcome email. A trip confirmation. A follow-up message. Write a detailed prompt and see what happens.

You’ll probably need to tweak it. That’s fine. The goal isn’t perfection out of the gate. It’s progress. And once you’ve got a prompt that works, you can reuse it, refine it, and build on it.

Automation doesn’t have to feel robotic. It just has to be thoughtful. And that part? That’s still on you.