The YouTube Rabbit Hole
A Bucket List Trip, Powered by AI | Part One
This is Part 1 of a six-part series about planning a 25th anniversary trip to Hawaii... and what happened when I stopped Googling and started talking to AI instead.
I’ve been planning my own trips since I was sixteen.
It started in the Netherlands. I was an exchange student living with a host family outside Amersfoort, and most weekends I’d show up at the train station with no plan beyond a vague sense of direction. I’d buy a ticket to some city I’d barely heard of... Delft, Groningen, Maastricht... and just go.
Photo: Amsterdam Central Station - August 20, 1992
That DIY instinct never left. After college, my roommate and I bought round-trip tickets to Brussels with zero hotel reservations and spent ten days drifting through Europe. After marriage and kids, Google made it manageable... Hotwire, TripAdvisor, the endless tabs open at 11 p.m. I used a travel agent exactly once.
Last year, I took my parents on a 14-day trip to the Netherlands. I planned the entire thing myself... day by day, city by city, train by train. Hotels in Amsterdam, The Hague, Maastricht, Vlissingen, Amersfoort. It took weeks of research, dozens of tabs, and a Google doc that got increasingly complex. The trip was amazing. But I realized afterward just how much time the planning had consumed.
I liked doing it myself. I liked the control. But there had to be a better way.
Photos: Biking and lunch on Texel Island, The Netherlands - May 2, 2024
In 2019, I found an article from The Telegraph: “The Best Beach Hotels in the Mediterranean.” Nicole and I were coming up on our 20th anniversary, and I wanted to do something that felt big. So in early 2020, we pulled the trigger. Cashed in frequent flyer miles, booked a week at the Hotel La Pérouse in Nice… this beautiful place perched on cliffs overlooking the Mediterranean. I built an itinerary: fly into Amsterdam, show Nicole where I’d lived as an exchange student, visit my host mom, then take a budget flight to Nice for the kind of bucket-list stay we’d been talking about for years.
You know what happened next.
March 2020. The world stopped. We postponed the trip a year. Then canceled it entirely. We spent our 21st anniversary in Chicago instead, which was lovely. But it wasn’t the south of France. It wasn’t what we’d been planning for.
Fast forward to 2025 and our 25th anniversary was coming up. Not a small number. Not a small feeling, either. We’d hit that point where “someday” trips start to feel a little too hypothetical. We didn’t want a fancy dinner where we’d spend half the time checking our phones. We wanted something that felt like a marker. A “we actually did it” moment. Something we’d revisit years later.
My American Airlines account was full of miles. It was time to try again.
It started in March with a YouTube video.
I don’t even remember what I was watching before it, but the algorithm served me this: The Ultimate Airline Pilot Experience: A Day in the Life Flying an A330 to Mauritius. Forty-three minutes of cockpit footage, island shots, and turquoise water that looked too perfect to be real.
I clicked.
Mauritius looked stunning. I’d never really thought about it before… didn’t know much beyond the vague sense that it was somewhere in the Indian Ocean. But watching that plane descend over the reef and the lush green mountains, I thought: Maybe that’s the trip.
Here’s where things went differently than they usually do.
Normally, I would’ve opened Google. Typed “best time to visit Mauritius” and started the spiral. Twenty tabs. Travel blogs from 2017. Reddit threads debating Mauritius versus the Maldives. TripAdvisor reviews that contradict each other. Three hours later, I’d be no closer to a decision and halfway to decision fatigue.
But I’d had a ChatGPT Pro subscription for months… told myself I needed to learn AI for work… and had barely used it. So instead of Google, I opened the app on my iPad and typed a question:
What is the weather like in Mauritius in September?
The response came back fast, but not like a search result. It was conversational. Apparently September is lovely… not as hot as summer, low chances of rain, great for outdoor activities. Then it asked me a question:
Are you interested in heading there for September?
I paused. This wasn’t how search engines worked.
I typed back: What airport would you fly into?
It told me about Sir Seewoosagur Ramgoolam International Airport. Gave me the location. Then asked again:
Are you planning a trip or just daydreaming for now?
I stared at my iPad.
Well, both kind of!
That’s when it clicked: This isn’t a search engine. It’s a conversation.
Over the next few days, I kept coming back to it. Not because I had to, but because the process felt different. Less like research, more like thinking out loud with someone who actually listened.
I asked about flights from Charlotte. The app told me the route options but also gently pointed out that Mauritius was far… and expensive. Did I want to consider closer alternatives with similar vibes?
I hadn’t asked it to do that. It just... offered.
So I asked: What are some closer options?
It suggested St. Lucia, Turks and Caicos, Aruba, Costa Rica, Puerto Rico. I scrolled through the list, and none of them grabbed me. We’d been to Costa Rica. The Caribbean islands all felt too familiar, somehow.
Then I typed: What about Hawaii?
I don’t know why I didn’t think of it earlier. We’d always wanted to go but had never pulled it off. Hawaii was one of those trips that sat in the back of our minds for years, growing a little bigger each time life handed us another reason to say “someday.”
ChatGPT came back with a breakdown of four islands… Maui, Kauai, Oahu, Big Island… each with a two-sentence summary of what made it different.
One stopped me cold:
Big Island (Hawai’i)
Relax factor: Black sand beaches, volcano views, and fewer crowds.
Adventure factor: Volcanoes National Park (maybe even see lava!), snorkel with manta rays at night, waterfalls and green sand beaches.
Vibe: Raw, wild beauty with plenty of space to explore.
Fewer crowds. A national park where you can hike across solidified lava. Snorkeling with manta rays at night. Raw, wild beauty… which made me think of St. John in the U.S. Virgin Islands, my favorite place we’d ever been.
I read it twice.
Tell me more about the Big Island.
It gave me a longer breakdown. Climate. Geography. The split personality of the island… Kona side versus Hilo side, dry lava fields versus rainforest. It mentioned Hawai’i Volcanoes National Park, Mauna Kea, the coffee farms, the beaches. The contrast between adventure and relaxation felt exactly right.
When I shared the idea with Nicole, something clicked instantly. Visiting Kīlauea had been on her bucket list for years. The moment I mentioned the Big Island and Volcanoes National Park, her eyes lit up. This wasn’t me selling her on a destination. We were both in.
So I went back to ChatGPT and it asked:
How long are you thinking for the trip? And are you looking for more adventure or more relaxation… or a mix of both?
I thought about it. Typed back:
We want both. Maybe start with adventure and hiking, then end with a resort where we can just relax by the water.
That’s a great structure. You could spend a few nights near Volcano for hiking, then move to the Kona coast for a beachfront resort. Would that work?
I sat there on my couch, iPad in hand, and realized something:
This wasn’t just answering my questions. It was helping me think. Organizing the mess in my head into something that felt like an actual plan.
Over the next few weeks, I came back to the conversation again and again. I asked about the weather in late September. What kind of rental car we’d need for the terrain. Whether it made sense to fly into Kona or Hilo. How many days to allocate to each part of the trip.
Every time I asked something, ChatGPT didn’t just spit back information. It asked follow-up questions. It helped me weigh options. It kept track of what I’d already told it so I didn’t have to repeat myself.
Two days before we left, I did something Nicole found hilarious.
I opened ChatGPT and gave it an inventory of all my relevant clothing… shirts, shorts, swim trunks, jackets, shoes. Then I told it to refer to the dates, the weather forecast, and our planned activities which it already knew.
Can you make me a packing list?
It came back with a detailed, organized list. Layers for the cooler elevation at Volcano. Reef-safe sunscreen. A light rain jacket. Trail runners and water shoes.
Nicole walked into the room while I was checking items off.
“Are you seriously having ChatGPT pack for you?”
“It’s... helping.”
She laughed. But the list was nearly perfect. And what’s normally a stressful, last-minute scramble turned into fifteen minutes of calm, methodical packing.
That’s when I knew this trip was going to be different.
Not because AI was doing the work for me. But because it was helping me think more clearly about what I actually wanted… and then getting out of the way so I could make it happen.
Photo: Walking off the plane into the Ellison Onizuka Kona International Airport - September 20, 2025
And then we stepped off the plane in Kona.
You know that wave of Hawaiian air that hits you the second you walk out of the airport? Warm, heavy, laced with flowers and ocean and something you can’t name?
That was the moment it became real.
The one where my brain finally let go of work and to-do lists and the everyday weight we carry without noticing. We were here. We’d made it. Twenty-five years. Hawaii. A trip actually happening… not someday, but right now.
The conversation that started with a YouTube video about Mauritius had turned into a weeks-long planning session that felt less like research and more like thinking out loud with someone who’d read every guidebook ever written.
And I was about to find out if it actually worked.
Next: Part 2 - Thinking Out Loud
Great start Jon...congratulations!