Not on its own. ChatGPT and other AI tools build Hawaii itineraries from blog posts, and a lot of those posts are four or five years old.
That means an AI Hawaii itinerary can include restaurants that have closed, drive times that haven’t been accurate in years, and activities with completely different rules than when the post was written.
AI can be a great way to get a really rough draft. But it only works if you really know the destination or can check with someone who does.
In episode 124 of my podcast, Hawaii Travel Made Easy, I share a consultation where a first-time family came very close to taking a trip that didn’t work. Below are the five problems I caught, so you can check your own plan against them, followed by the full transcript.
🎧 Listen to the Episode
Listen to Ep 124: AI Wrote Their Hawaii Itinerary
Key Takeaways From This Episode
- AI itinerary tools pull from blog posts, and many of those posts are four or five years old.
- One family’s 7-day Maui and Big Island plan had close to 10 hours of avoidable driving, two full-day activities stacked on the same day, and a boat trip described as two different excursions.
- It also had them stargazing at the Mauna Kea summit, which isn’t recommended for kids their age.
- With one week, you’re almost always better off picking one island instead of two.
- If you already have an itinerary, a Hawaii itinerary review or a consultation catches these problems before your trip.
The Itinerary This Family Sent Me
A couple booked a consultation with me and sent their itinerary over before our call.
The husband had been to Maui once. His wife and their two kids had never been to Hawaii at all. This was going to be their first family trip, and they wanted to get it right.
The plan came from a travel agent who claimed to specialize in Hawaii. I opened the file expecting to do some light tweaking. Within the first page, I could tell something was off.
Once I saw the pattern, I recognized the agency’s name. It’s a company that leans heavily on AI, and the itinerary read like something that had been assembled instead of lived.
I was ready to spend the first 20 minutes of our call convincing them to scrap it. I didn’t need to. The wife told me she’d had a feeling something wasn’t adding up, and she was relieved someone could finally tell her why.
5 Problems to Check Your Own Itinerary For
These are the exact things I flagged in their plan. If you have a ChatGPT Hawaii itinerary sitting in a doc right now, go through it with this list.
1. Long day trips that should have been an overnight
They were staying in Kona the entire time but driving to Hawaiʻi Volcanoes National Park and Hilo on two separate days.
That drive is a little over two hours each way. Doing it twice adds up to close to 10 hours in the car, for something that would have been much easier with one night booked near the park.
On your own plan, add up the round-trip drive for every day trip. If the same long drive shows up twice, that’s your sign to look at staying a night closer.
2. Two full-day activities on the same day
Their Road to Hāna day also had stargazing at Haleakalā that night.
The Hāna Highway takes a full day on its own. My own Road to Hāna day ran 13 hours from start to finish.
Haleakalā stargazing is another four to five hours. Their plan put that on top of the Hāna drive, with a nine-year-old.
Look at what’s scheduled after every big driving day. If there’s another major activity that evening, one of them needs to move.
3. One boat trip described as two different excursions
The itinerary referenced a Molokini boat trip in one paragraph. A few pages later, it called the exact same excursion a Lānaʻi snorkeling trip.
Those are two completely different boat rides to two completely different islands.
Read your itinerary all the way through and make sure each tour is described the same way every time it comes up. If the name or the island changes partway through, find out which trip it really is before you book.
4. An activity that doesn’t fit your kids’ ages
They were booked for stargazing at the Mauna Kea summit. The official guidance is that kids under 13 shouldn’t go up there at all, and one of their kids was nine.
For every activity on your list, look up the age guidance yourself. Don’t assume the itinerary already did.
5. Two islands squeezed into one week
The plan had them splitting seven days between Maui and the Big Island.
With one week, you’re almost always better off picking one island instead of stretching yourself across two. It comes down to matching your time to what one island can actually give you instead of racing between them.
If your trip is a week or less and has an island hop in it, that’s the first thing I’d question. My episode on which Hawaii island is best for families can help you pick.
Why AI Gets Hawaii Itineraries Wrong
ChatGPT has never sat behind a rental car going 15 miles an hour around a blind curve on the Road to Hāna. It only knows what the blog posts say, and those aren’t what they used to be.
I’ve run Hawaii Travel with Kids for about eight years, and there was a stretch where my site showed up first no matter what you searched, because I kept it current.
Google’s algorithm has shifted a lot since then. A lot of what ranks now is AI-generated, sponsored, or written by someone who visited once five years ago and never touched the post again.
So the top Google result you’re pulling your itinerary from might not be current. It might not have been written by a person, either.
Is a Travel Agent’s Itinerary Any Safer?
Not automatically. The plan in this episode came from one.
Plenty of agents really do care about your trip. But a lot of Hawaii knowledge in the industry comes from hotel tours. That’s great for picking a resort. It doesn’t mean they’ve ever driven the Road to Hāna.
What We Did Instead
We scrapped the itinerary and started over.
The wife had been talking to friends who’d been to Hawaii, and she’d already landed on the one-island idea herself. We chose Maui for the full week.
It gave them that classic, iconic Hawaii feel with a mix of resort time and real adventure, without the constant driving. I told them this trip is going to get them hooked, and their next one can be the Big Island done properly, with the time it deserves.
If you’re weighing those same two islands, listen to episode 116 on Maui vs. the Big Island and episode 117 on why the Big Island doesn’t work as a four-day add-on. And if you land on Maui too, grab my Maui travel guide for families.
How to Get Your Hawaii Itinerary Checked
It doesn’t matter if your itinerary came from a travel agent, a Facebook group, or ChatGPT. This is exactly the situation a review or a consultation is built for.
My Hawaii itinerary review is $50. You send me your itinerary as a Google Doc or PDF with up to 5 questions, and I return it within 2 business days.
I tell you what works, what doesn’t, and what I’d change. That includes drive times that don’t add up, activities that don’t fit your kids’ ages, and days that are just too packed.
Want to see what you get back? Here’s a real Hawaii itinerary review example.
If you’d rather talk it through, you can book a 60 or 90-minute call with me as a Hawaii travel consultant for families. We go through your plan line by line and fix the parts that don’t work.
A couple of things to know first. I’m not a travel agent and I don’t book anything. You book it all yourself. My recommendations sometimes include affiliate links, so I may earn a small commission if you book through them, at no extra cost to you.
I’m a professional tourist with 40+ Hawaii trips behind me, and I’m a Hawaii Tourism Authority Certified Hawaii Destination Expert.
I’ve done the vast majority of what I recommend myself, whether that was solo, as a couple, with young kids, with friends, or on a multigenerational trip. For the handful of things I haven’t done personally, I’ve talked directly with people who have.
Don’t have an itinerary yet? Start with my Hawaii trip planning page.
Frequently Asked Questions
Is ChatGPT good for planning a Hawaii trip?
It can be a great way to get a really rough draft. But it only works if you really know the destination or can check with someone who does. ChatGPT builds itineraries from blog posts, and many of those are four or five years old, so I wouldn’t book anything straight from what it gives you.
What does AI get wrong about Hawaii itineraries?
Drive times that don’t add up, activities that don’t fit your kids’ ages, and days that are too packed. In the plan from this episode, I found close to 10 hours of avoidable driving on the Big Island, the Road to Hāna and Haleakalā stargazing on the same day, and one boat trip described as both Molokini and Lānaʻi. AI also pulls from old posts, so it can list restaurants that have closed and rules that have changed.
Can someone check my AI-generated Hawaii itinerary?
Yes. That’s what my Hawaii itinerary review is for. Send me your AI Hawaii itinerary as a Google Doc or PDF with up to 5 questions, and within 2 business days I’ll tell you what works, what doesn’t, and what I’d change.
How much does a Hawaii itinerary review cost?
$50. I’m not a travel agent, so I don’t book anything for you. You get my notes and then book it all yourself.
Should I split one week in Hawaii between two islands?
With one week, you’re almost always better off picking one island. This family’s original plan split seven days between Maui and the Big Island. We changed it to a full week on Maui, with the Big Island saved for a future trip.
Full Podcast Transcript
This transcript has been lightly edited for readability.
Why AI itineraries miss so much about Hawaii
ChatGPT has never sat behind a rental car going 15 miles an hour around a blind curve on the Road to Hāna. It has never had to tell a mom of two that her nine-year-old can’t go to the summit of Mauna Kea. It has never once looked at a family’s energy level on day four and said, “Maybe we skip this one.”
It’s pulling from blog posts. So is every free AI itinerary tool flooding your feed right now.
And here’s the part that doesn’t get talked about enough. A lot of those blog posts are four or five years old. They’re describing restaurants that closed, drive times that haven’t been accurate in years, and activities that now have completely different rules than they did when the post was written.
There’s a real difference between an itinerary built by someone who’s made the drive 100 times and one that’s assembled by a system that’s never left a server room.
I had a consultation a few weeks ago that showed me exactly how much that difference matters, and how close one family came to finding out the hard way.
The consultation that started with a bad itinerary
Welcome back to Hawaii Travel Made Easy. I’m Marcie, and today I want to walk you through a consultation I did recently, because it’s one of those calls that reminded me why this part of my job matters so much.
A couple had booked a consultation with me, and before our call, they sent over an itinerary that had been given to them by a travel agent who claimed to specialize in Hawaii.
The husband had been to Maui once before. His wife and their two kids had never been to Hawaii at all. This was going to be their first family trip, and they wanted to get it right.
I opened the file expecting to do some light tweaking. Instead, within the first page, I could tell something was off.
The red flags in their plan
The itinerary had them spending seven days split between Maui and the Big Island, staying in Kona the entire time, but driving to Hawaiʻi Volcanoes National Park and Hilo on two separate days.
That drive is a little over two hours each way, so doing it twice adds up to close to 10 hours in the car across the trip, for something that would have been much easier with one night booked near the park instead.
Then there was the Road to Hāna day. The same day they’d be driving the Hāna Highway, a road that takes a full day on its own, they were also scheduled for stargazing at Haleakalā that night. That’s a four to five-hour experience after a 12-hour driving day with a nine-year-old.
And buried in there, the itinerary referenced a Molokini boat trip in one paragraph and then called the exact same excursion a Lānaʻi snorkeling trip a few pages later. Two completely different boat rides, two completely different islands.
It also had them booked for stargazing at the Mauna Kea summit, even though the recommendation is that kids under 16 shouldn’t go up there at all. [Editor’s note: The official guidance is that kids under 13 shouldn’t go past the visitor station.]
This is exactly what travelers get wrong about Hawaii when they’re relying on something that was assembled instead of lived.
Why it was so wrong
Once I saw the pattern, I actually recognized the name of this particular travel agency. There’s been a lot of talk in the industry about this company leaning heavily on AI, to the point where some people question whether the person you’re emailing with is even a real employee.
That’s an unsettling thought when you’re handing someone thousands of dollars to plan your family’s trip.
Starting over with one island
I started the call by telling them straight up that I had some real concerns about what they’d been sent. I was ready to spend the first 20 minutes convincing them to scrap it.
I didn’t need to. The wife told me she had a feeling something wasn’t adding up, and she was relieved someone could finally tell her why.
We scrapped the itinerary and started over.
She had been talking to friends who’d been to Hawaii, and she’d already landed on something I talk about constantly, whether it’s on this podcast, the blog, or Instagram. With one week, you’re almost always better off picking one island instead of stretching yourself across two.
That’s really the heart of how to choose a Hawaii island: matching your time to what one island can actually give you instead of racing between two.
If you want the full case for that, go back and listen to episode 116, where I break down Maui versus the Big Island, and episode 117, where I get into why the Big Island specifically does not work well for a four-day add-on to a longer trip.
We landed on Maui for the full week. It gave them that classic, iconic Hawaii feel with a mix of resort time and real adventure, without the constant driving.
I told them this trip is going to get them hooked, and then their next trip can absolutely be the Big Island done properly, with the time it deserves.
Travel agents, FAM trips, and outdated search results
I want to be really clear. I’m not saying every travel agent is unreliable or that AI is some kind of villain. Plenty of agents really do care about your trip.
But a lot of Hawaii knowledge in this industry comes from what’s called a FAM trip: hotels flying agents out to tour their properties so they can sell them later. I’ve heard about agents touring ten or fifteen hotels in a single day.
This is great for picking a resort. It doesn’t mean they’ve ever driven the Road to Hāna or done a single activity they’re recommending to you.
And here’s the other piece. I’ve run my Hawaii Travel with Kids blog for about eight years, and there was a stretch where my site showed up first no matter what you searched, because I kept it current.
Google’s algorithm has shifted a lot since then, and a lot of what ranks now is AI-generated, sponsored, or written by someone who’s visited once five years ago and never touched the post again. I’ve watched people who actually know these islands get buried under that.
So that top Google result you’re pulling your itinerary from? It might not even be current, and it might not have even been written by a person.
What backs up my advice
Forty-plus trips is what backs up everything I say on this podcast. I’ve done the vast majority of what I talk about myself, and for the handful of things I haven’t done personally, I’ve talked directly with people who have.
I’ve traveled these islands solo, as a couple, with young kids, with friends, and on multigenerational trips.
That’s really why people started calling me a Hawaii travel specialist. Not because I put it on a business card, but because [I’ve] actually done the experiences.
Consultations and itinerary reviews
If you already have an itinerary in hand, whether it came from a travel agent or a Facebook group, or you asked ChatGPT to build it for you, this is exactly the situation a consultation is built for.
We’ll get on a call, I’ll go through it with you line by line, and we’ll fix the parts that don’t work so you can avoid Hawaii travel mistakes before they turn into a stressful day on your actual trip.
That’s really what Hawaii itinerary planning should look like: someone who’s actually done the drive checking your plan before you’re the one behind the wheel finding out it doesn’t work.
You can book a sixty-minute or a ninety-minute consultation at hawaiitravelwithkids.com under Hawaii Travel Consultant.
If a full call isn’t what you need right now and you just want a second set of eyes to catch the big red flags, my fifty-dollar itinerary review is a great starting point. Send me your day-by-day plan and I’ll flag anything that’s going to cause problems: drive times that don’t add up, activities that don’t fit your kids’ ages, days that are just too packed.
You can find that at hawaiitravelwithkids.com under Hawaii Itinerary Review.
Whichever one you choose, the goal is the same: giving first-time Hawaii visitors, or even repeat visitors trying something new, realistic Hawaii travel expectations instead of a hopeful guess.
One more thing
If this episode just saved you a few hours of digging through outdated blog posts, or made you second-guess an itinerary you already have in hand, leaving a quick review for this podcast actually makes a real difference. It’s one of the easiest ways to help other listeners find their way to the show before they end up in the same spot that couple did.
I’ll see you next time. Aloha.
Not Sure Your Itinerary Holds Up?
That feeling the wife had, that something wasn’t adding up, is worth listening to.
Send me your plan for a Hawaii itinerary review and find out now, while it’s still an easy fix on paper and not a 13-hour day in a rental car.
 | About the author: Marcie Cheung is a Hawaii travel consultant for families who has visited Hawaii more than 40 times. She is the founder of Hawaii Travel with Kids and host of the Hawaii Travel Made Easy podcast. She offers one-on-one Hawaii trip planning consultations and itinerary reviews for families, couples, and honeymooners. |