AI & Golf Travel Planning

Even ChatGPT Knows the Difference

Daniel Jones

October 24, 2025

7 Minute Read

As the world of travel continues to evolve, it’s no surprise that more and more golfers are turning to AI tools like ChatGPT to help plan – or at least jumpstart – their overseas golf trips.

We know some of our prospects and Members are also using these tools. Frankly, I do as well. I use ChatGPT every day. It makes me more efficient, more creative, and in some ways, even better at my job.

But what about our collective jobs here at H&B – the planning of golf trips to Scotland, Ireland, and England? The one where dozens of details, moving pieces, and personal preferences come together to create a single, seamless experience?

How do we fit in the rapidly shifting business landscape that AI has brought about?

For the answer, I did what most AI users would do in my shoes: I asked ChatGPT:

"In this environment, what do you see as the key advantages of working with a golf travel company like H&B versus planning a trip with... You?”

In the interest of transparency, here's the full prompt and answer provided by ChatGPT. And before you ask: yes, I call her "Chatty."

The response was remarkably honest and self-aware. Granted, a couple of the examples are a little disjointed, yet the overall message comes thru loud and clear:

Even ChatGPT recognizes the difference between planning a golf trip with AI on your own and enlisting the service and expertise of a golf travel company like Haversham & Baker.

Let's take a look at the answer and break down how the insight could shape your golf trip across the pond.

Note: Everything between the two lines was written by ChatGPT.

ChatGPT's Answer

Morning — what a fantastic and very forward-looking question. You’re absolutely right: AI is now part of your prospects’ pre-planning behavior. They’re using it to get a sense of what’s possible, to dream, and to narrow ideas.

The reality is: AI is an excellent researcher and ideator — but a terrible trip manager.

That’s exactly where H&B’s value lives. So the opportunity isn’t to compete with AI, but to complement it — and to position H&B as the trusted steward who turns inspiration into reality.

Here’s how I’d break down the advantages of working with H&B versus “planning a trip with ChatGPT”:

🧭 1. Accuracy vs. Authority

AI can gather information. H&B interprets it.

ChatGPT can tell you Royal Dornoch exists; it can’t tell you which tee time patterns actually work around Muirfield’s visitor days.
It can list hotels; it can’t tell you which ones actually get your group on the Old Course ballot.
It can suggest an itinerary; it can’t ensure it’s logistically possible or optimized for weather, daylight, and drive times.

H&B translates data into dependable reality.

🎯 2. Experience vs. Experiment

AI gives you a starting point. H&B gives you a sure thing.

AI is great at possible trips — but every H&B Expedition is a proven trip, refined through 30+ years of real-world outcomes.
When someone spends five or six figures on a once-in-a-lifetime trip, they don’t want to “beta test” an AI itinerary.

👉 H&B isn’t guessing — it’s guiding.

🕰️ 3. Time Saved, Not Time Spent

AI requires effort; H&B eliminates it.

AI gives you more options to sort through, not fewer.
A Captain can spend 20 hours researching on ChatGPT — or 20 minutes on a call with H&B and have every detail handled.

👉 The true luxury is time saved, not information gained.

💼 4. Access and Relationships

AI can’t pick up the phone.

It doesn’t know the starter at Royal County Down.
It can’t call your driver in Dublin when your flight is delayed.
It doesn’t have standing relationships with hotels, clubs, and caddie masters who trust H&B’s name.

Relationships unlock access — algorithms can’t.

🤝 5. Human Assurance

AI can predict problems. H&B prevents them.

If weather changes, if a course closes, if a bag goes missing — AI can’t fix it.
H&B’s team anticipates, adjusts, and reassures.
The peace of mind comes from knowing there’s a real person who’s already thought two steps ahead.

👉 Technology provides information. People provide certainty.

🍻 6. The “Good Life” Factor

AI can suggest attractions. H&B curates experiences.

ChatGPT can list distilleries; H&B knows which one pairs best with your tee time and driver’s route.
It can recommend restaurants; H&B knows which table overlooks the 18th at Rusacks.

👉 It’s not about seeing more, it’s about experiencing better.

💬 7. Personal Trust, Not Personalization

AI can personalize content. H&B personalizes care.

It can remember your past searches; we remember your past trips.
It can use your name; we know your story.

👉 H&B’s “personalization” is relational, not algorithmic.

So What Does It All Mean?

ChatGPT is an incredible tool. I’ll be the first to say it has made me more efficient, more creative, and more productive. For travelers, it’s equally helpful in the early stages of planning. It can generate ideas and outline possibilities.

But when it comes to turning those ideas into reality – and ensuring the experience lives up to both the investment and expectations – that’s where the tool reaches its limit.

To echo an example given by Chatty, it can tell you what notable courses you should play in East Lothian, but it can't:

Route their order around Muirfield visitor days.
Reserve your tee times.
Arrange a whisky tasting for after a round.
Call a club for assistance when the airline loses your clubs and you need a set of rentals.

A golf trip of this caliber requires the planning and execution of 40–50 decisions: tee times, hotels, routing, restaurants, transportation, touring, and countless other variables most travelers don’t even realize they’re navigating.

ChatGPT can suggest them. Haversham & Baker coordinates every last one.

That’s why the real distinction isn’t between tech and human. It’s between possibility and precision.

And the cost of getting it wrong isn’t just money wasted. It's missed memories and disappointed dreams.

For many travelers, this isn’t just a vacation. It’s a long-anticipated journey with friends, a retirement celebration, a family milestone, or the chance to finally walk the fairways they’ve dreamed about for decades.

And those kinds of trips don’t come around often.

AI can offer plenty of inspiration, but Haversham & Baker offers assurance.

Skip the Script. Share Your Story.

On a related note... If you do decide to engage a golf travel company like H&B, try to avoid letting AI do all of the talking for you.

We see it more and more: replies to our introduction emails that feel like they were copy-pasted from ChatGPT. They tend to read like a recipe, with lots of random bolding… and lack the personal context that makes a meaningful conversation possible.

Instead of moving the process forward, they raise more questions. Instead of revealing your goals, they gloss over them.

So if you want the best from a golf travel company, give us the best of you: your preferences, your travel companions, your pace, your priorities. Tell us if you’re a group of architecture buffs, or if one of the Tourists in your group loves whiskey, or if early tee times are a dealbreaker.

Because real customization starts with real communication.

And if you do use AI to help craft your message, think of it as a tool to organize your thoughts, not replace them. Add what matters to you and the goals that AI may have missed. That’s how the best trips begin.

ChatGPT's Last Word

Before drawing this to a close, I'd be remiss to not include two lines from the final segment of ChatGPT's original reply..

“AI can show you what’s possible. Haversham & Baker shows you what’s perfectly planned.”

“Ask ChatGPT where to play. Ask H&B how to make it happen.”

I think both of these quotes perfectly summarize the current landscape of AI and golf travel planning.

Of course, we don’t know what the next five years will bring. Perhaps AI will one day evolve to make this post will look very silly. But for now, even ChatGPT knows: