Yesterday morning our alarms went off at 2 a.m., and a half hour later we headed down to the ballroom of the Crowne Plaza Resort in Asheville with our backpacks and two “comfort packs” stuffed into large plastic garbage bags.

Only six hours earlier, we had gathered in this same room for dinner, a briefing on the next day’s gameplan, and a mission moment to remind us all why we were here. A fellow hiker and dad of an 11-year-old boy with Cystic Fibrosis told the story of his son’s diagnosis, but more importantly his son’s life... his current involvement in theatre and his aspirations of making video games. We even got a video sendoff from the kid back in Ohio. Let me tell you, this kid definitely belongs in show business!

We had all been training for this weekend for months. I had simultaneously been doing PT ever since surgery to repair a meniscus tear in my left knee back in October. Once my physical therapist cleared me, I started running again, and by my count have logged over 105 miles of training hikes since January.

But this weekend, I was getting ready to do something I’d never done before. Hike approximately 30 miles on the Appalachian Trail in one day. One of the most rugged and technical trails in the mountains of North Carolina.

Just before dinner on Friday night, I stopped to chat with one of the coaches I’d hiked with a few times during training and had talked with about my recovery from knee surgery. He asked how I was feeling about the next day, then in a calm, reassuring voice simply said, “You’re ready.” Those two words kept me from being a complete ball of nerves that evening.

Things were actually looking up for this spring’s Xtreme Hike, organized by the North Carolina Chapter of the Cystic Fibrosis Foundation. When I packed earlier in the week, the weather forecast looked terrible: cold, rainy, and windy most of the day with a chance of thunderstorms. By the time we sat down for a buffet dinner with half a dozen kinds of pasta, the forecasters were only calling for a slight chance of drizzle. I kept everything packed as I had it, just in case. Two things had given me pause about signing up for this hike in the first place: the fundraising and the weather. The fundraising had ended up working out great, and now it looked like the weather was going to cooperate as well.

We dropped off our comfort packs with some of the dozens of organizers and volunteers supporting this hike. We took a big group picture in the parking lot and boarded passenger vans for the hour-and-15-minute ride to the trailhead.

My team, Reece’s Monkeys, was the fifth group of six to set out on the trail. The team is named after Reece, the now teenage son of our friends April and Brent. Reece has CF, and his mom April organized the team. Our son Zach and Reece have been close friends since they played soccer together as little kids. There was a little bit of waiting in the dark before it was time for one final picture behind the start banner. Then we set out single file into the woods, with only our headlamps to light the way.

The first 6 miles of the trail were relatively easy and pleasant. It was a brief climb to get up to the top of Max Patch, which I hear has spectacular views, but in the dark I couldn’t see anything but lights way off in the distance. The temperature was in the low 40s, and it was pretty windy. We descended back into the forest, hiking along a creek and crossing over it multiple times. There was still quite a bit of cloud cover, so we really didn’t get much of a sunrise other than the gradual lightening of the sky. Just before it started to get light, the birds in the trees suddenly erupted into song. There had to have been thousands of them up there, and it was unlike anything I’ve ever heard! Gradually the sky got lighter, we were able to turn off the headlamps, and before long we made it into Aid Station 1 at approximately 6.2 miles in.

The volunteers there were making cinnamon rolls on a griddle and had various other snacks and candy available. I had ended up as one of the last hikers to come into that aid station, and I really didn’t want to be at the tail end of the hike all day long. I waited about two minutes for a hot cinnamon roll to come off the griddle, ate it, grabbed my pack, and hit the trail again without sticking around too long.

Now the trail started to show off its real personality. We had a decent uphill climb out of Aid Station 1, and I actually passed a few people on the way up. Then for the first large downhill stretch, I decided it would be easier on my knees if I jogged it. That turned out to be a big mistake. While the jog itself was fine, when I got to the bottom and had to start heading up again, I had completely zapped all of my energy. It took everything in me to take each step up that hill, digging my poles into the ground and moving at an excruciating pace. I went from a 16-minute mile to a 28-minute mile just like that, and everyone I had passed earlier passed me, and then some.

While I’d hiked the first six miles with a group, this stretch I had been mostly by myself. I was starting to wonder if I was going to be alone for the entire hike, which didn’t seem like much fun. I just wasn’t pacing along with anyone else. They would pass me on the uphills, and I would catch up and pass them on the downhills, never quite syncing with anyone the way I had on the training hikes. At this point I was also seriously questioning whether or not I was going to be able to complete this hike.

After one particularly long stretch by myself, I looked behind me and Stacy, Brent’s sister and one of Reece’s aunts on the team, was coming up. We both lamented the long slog uphill we’d just done, and then ended up hiking the rest of the day together, keeping each other company. Taking the uphills slow, regaining a solid pace on the flats and downhills.

Aid Station 2 at about 14 miles in was a welcome break. In my comfort pack I had a fresh pair of socks and my other pair of trail runners... ones with a little more cushion than the ones I’d chosen for the first half. I’d been carrying a massage gun in my pack all day, and the extra weight finally paid off as I worked on my legs sitting barefoot in a camp chair. The volunteers there were making grilled cheese sandwiches. Plain white bread, slathered in mayonnaise, filled with what was certainly not real cheese, then cooked on a griddle. The cheese was literally dripping out into the aluminum foil wrapper as I ate it, and after that much time on the trail, it was absolutely delicious!

But we still had the second half of the hike. I laced up my second pair of trail runners, refilled my water bladder, and Stacy and I set off. There were a lot of debates afterward about how rough this stretch of the trail was, but I honestly don’t remember it being that bad. Sure, there were uphills, and sure, Stacy and I took them slower than we did on the rest, but it seemed manageable. It was during this stretch that the sun actually started to come out, and we could see a gorgeous blue sky up through the trees. As we got closer to the town of Hot Springs, we could hear live music from a festival being held down in the valley, getting louder as we approached the town.

Aid Station 3 was right where the trail hits the town of Hot Springs. As I approached it, some AT thru-hikers sitting on their packs greeted me. As the cheering and cowbells started up around the corner at Aid 3, they asked, “Is that cheering for you?” I embarrassedly admitted that it probably was, and they started clapping and cheering too!

At Aid 3 the volunteers had more grilled cheese, but also hot homemade chicken tortilla soup. It was absolutely amazing and hit the spot. But with 8 more miles to go, we didn’t hang around too long. At this point I was feeling better about finishing... the cutoff time for leaving Aid 3 was 3:30, and it was only 1 p.m.

We walked through downtown Hot Springs and then back onto the trail. It started off easy enough, almost like a greenway along the river. Then a left-hand turn... and straight up. Like we did 1,000 feet in less than 2 miles!

Each time we reached a turn in the trail, we thought for sure we’d be done gaining elevation. Nope. More uphill. There were a lot of f-bombs during that stretch! It was absolutely grueling, especially after already putting in 21 miles that day and being up for 12 hours.

We did a lot more climbing until the last mile or so. Then finally, on what seemed like an easy stretch after what we’d been through, we heard music playing in the distance, and the trail suddenly popped out onto a road. Across the bridge, hikers and volunteers were cheering and ringing cowbells.

And just like that, we were done. Sitting in camp chairs, feet in sandals instead of hiking boots, with a beer and a slice of pizza. No more miles. No more inclines.

Looking back at the day in the Fitness app on my iPhone, there were a bunch of “awards”... longest hiking workout, new exercise record, hiking elevation gain record, new move record (3,747 calories). In an instant I went from “I’m not sure I’m going to finish, and I’m never going to do this again” to “what can I do better next year?”

Two things for sure. Don’t try to run, and consume more food. When I think back at how little food I ate and how many calories I burned, it’s no wonder I struggled. Not that the hike would have been easy... they call it “Xtreme” for a reason. But definitely room for improvement.

It’s a grueling day, regardless. But the sense of accomplishment is exhilarating. And one thing is clear. The breathless inclines, sore feet, and tight muscles I felt for a day are nothing compared to what people with CF live with every day. The hours of airway clearance and nebulizer treatments. The pancreatic enzymes with every meal and snack. The lung infections that don’t always respond to antibiotics. The “tune-up” hospital stays that can stretch into weeks at a time. That’s their normal. This is why we hike... sure, because we wanted a challenge, but more importantly to help find a cure for a disease that turns so many lives upside down.

Sitting at the breakfast celebration this morning in the ballroom of the Crowne Plaza in Asheville, I thought about the breakfast I attended as a family member the year before, after my wife and son had finished their second hike. In my last post I wrote about how that inspired me to join this incredible community. And now, having stepped off the sidelines, it’s amazing to be a part of this special family, all united for a worthy, and achievable, cause.

I want to extend a heartfelt thank you to my amazing supporters who made all of this possible with their generous donations to the Cystic Fibrosis Foundation.

My parents Bill & Suzy, my sisters Beth Assis and Emily Costa, my two best friends Andrew Schulz and Josh Strecker, friends I haven’t seen in years like Matt Christina, Steve Sutton, Matt Starnes, and Rob Floyd, my cousin Van Weston, family friends Carrie & Terry Kennedy, John & Lisa Kawyn, Aaron Leaver & Krissy Fox, leaders at my employer Veylan: Anthony Iacovone, Quique Nagle, and Lynn Browne, current and former colleagues Jeff Wheeler, Kus W, Dave Imrem, Ashley Saville, Jenn Jackson, Nolen Mabie, Tom Jackson, Tim Pollock, Carol Poteat, Tim O’Connell, Kerin Rue, Gale Bonnell, and Neal Sharpe. I was also genuinely moved by folks I didn’t necessarily expect to hear from, who saw my LinkedIn posts and graciously clicked to make a donation. My dad’s former colleague Chuck Millsaps, and business contacts like Susy Schwede, Lena Rodriguez, and Andy Shepard. And the handful of others who wished to remain anonymous.

You all donated to a great cause, but your donation also told me you were rooting for me as I took on this challenge, and I am forever grateful and deeply touched.

This spring’s hike had a smaller number of participants than years past, but we still managed to raise $233,416 (as of this morning) in the fight to cure Cystic Fibrosis. We’re still trying to reach our $370,000 goal. It’s not too late to help us close the gap.

• My page: https://fundraise.cff.org/springhike2026/jonathan

• Nicole’s page: https://fundraise.cff.org/springhike2026/Nicole

• Zach’s page: https://fundraise.cff.org/springhike2026/Zach

The morning after the 2025 North Carolina Spring Xtreme Hike to benefit the Cystic Fibrosis Foundation, I sat at breakfast on the pool deck of Harrah’s Cherokee Casino and listened to people tell stories about their day on the Appalachian Trail.

This was new for me. My wife Nicole and our son Zach had just finished their second Xtreme Hike, on a team with our friend April, her sister, and her sister-in-law. The first two years I’d cheered from the sidelines... tailgating at aid stations, waiting at the finish line, proud of them but quietly thinking I’d never put myself through that kind of punishment. I’d hung out with everyone the night before at dinner, staying up way too late with a group of people who had just spent twelve-plus hours on the trail. But the breakfast was different.

People were trading stories about magical moments on the trail. Striking up a conversation with someone they’d never talked to before and ending up in a long, deep one. The strange emotional weight of finishing something that hard. I was watching, from the outside, a community that had pulled itself together from every direction... parents of kids with cystic fibrosis, grandparents, friends, people living with the disease themselves, and a not-insignificant number of people with no personal connection to CF at all. Through some event or just the appeal of the hike, they’d become true believers in the cause.

That was the moment I decided I was in. At lunch on the drive home, I told the rest of Nicole’s team.

I had to announce it before I chickened out.

That was May. In July, I tore the meniscus in my left knee helping a friend load a U-Haul. A month and a half with a sports chiropractor ended at an orthopedic surgeon’s office, where I learned I’d need surgery. I stayed active through all of it... running, going to training hikes with the Fall Xtreme Hike group, and keeping up on our 25th anniversary trip to Hawaii’s Big Island. The surgery happened in October. I started PT right away and slowly built back up before hike training started in January.

I’ll be honest, the first few training hikes weren’t the magical events I’d imagined from those breakfast stories. I was so focused on not re-injuring my knee that I barely noticed I was outside. Then, after one of them, I saw a post in our Facebook group from one of the coaches. It was beautiful and a little poetic... a description of the nature he’d noticed that day, with gorgeous pictures from the same trail we’d just hiked.

I hadn’t noticed any of it. I hadn’t taken a single picture.

When was the last time you were in nature? Like, really in nature. For me, it’s not something I experience often enough. As I write this, I’m sitting on my back patio in the last couple hours of daylight, a cool breeze coming through. The view is fine. A 180-degree wall of green trees. But I can’t see the horizon, and it feels closed in. The noise of modern machinery never quite stops, either. Cars on the nearby road, lawn mowers, leaf blowers. The major irritant last Friday was the generator on the mobile dog groomer’s truck two doors down!

On the next hike, I made a point of not always looking at my feet. I looked at the views. The signs of spring breaking out along the trail. The quiet of the forest, broken only by the occasional plane overhead. The peak of a mountain wrapped in fog. I was finally taking it in.

And as I started paying attention to the trail, I started paying attention to the people on it.

The trash cans. If you know, you know.

Real community is something I’d been quietly looking for, for years. I’d tried the places where it’s supposed to be easy to find, the ones that put it right on the welcome sign. For me, it mostly didn’t take. What was happening on these training hikes was different.

The format almost forces it. Pace varies, the line stretches and clumps, and you end up hiking next to whoever you end up hiking next to. The conversations range from the mundane, like what people do for a living and how training is going, to the deeply personal, to the absurd. We all have different things motivating us, but we’re all here for the same reason. I’m not someone on the sidelines anymore, watching this play out in other people’s lives. I get to be in it.

We finished our last training hike this morning... just over seven miles, on a familiar trail we’ve done more than a few times. As we started, I noticed a chorus of birds overhead in the trees. Thousands of them, it sounded like. Unlike anything I’d heard before. At the top of Crowders Mountain, instead of snapping a quick picture and plowing through like we usually do, we all paused. Took it in. Took more than a few pictures.

This Saturday, we’ll wake up hours before sunrise and get dropped off in the dark on the Appalachian Trail. It will be grueling. But through the chaos of life and work this week, I’ll be looking forward to spending an entire day in those mountains with this group of people I’m proud to call friends. Hoping that, eventually, our efforts will help make CF stand for “Cure Found.”

Another trash can selfie. It's a whole thing now.

If you’d like to support our hike, here are our fundraising pages. Every dollar goes to the Cystic Fibrosis Foundation.

• My page: https://fundraise.cff.org/springhike2026/jonathan

• Nicole’s page: https://fundraise.cff.org/springhike2026/Nicole

• Zach’s page: https://fundraise.cff.org/springhike2026/Zach

I was at work, washing down a Twix bar with my second Dr. Pepper of the day. Probably my second of five. My phone rang. It was my doctor with the results of my recent blood work.

You have diabetes.

I don’t remember much of what he said after that. I remember the advice, though, because it was spectacularly unhelpful. Stop eating sweets. Lay off the cake, the ice cream, the sodas. That was about it. No real plan. No framework. Just... stop doing the things you’re doing.

I fired that doctor not long after.

But replacing the doctor didn’t replace the confusion. What started that day was nearly two decades of managing a disease mostly in the dark.

Here’s how diabetes management worked for me, for a long time. I had a glucose meter. I could prick my finger, get a number, and know what my blood sugar was at that exact moment. One moment. One snapshot. And to do it properly, one snapshot wasn’t enough. You’re supposed to test multiple times a day, at precise intervals. Before meals. Two hours after meals. Before bed. It becomes the organizing principle of your entire day. I wanted to control this thing, but I could never get on board with a lifestyle that revolved around a needle and a timer. So I’d try for a day or two, then not test at all for weeks. Then every three or four months, I’d get my A1C results back and hold my breath.

The A1C was always a surprise. Sometimes better than expected. Usually not. And the frustrating part was that I could never connect the dots between what I did day to day and what that number said about the last ninety days. It was like getting a grade on a test where nobody showed you the questions.

I tried different medications over the years. Some worked better than others. Some made me gain weight. Some made me lose it. One made me nauseous enough that I dreaded taking it. They all moved the needle in varying degrees, but none of them gave me the thing I actually needed. Which was understanding.

It was easier, in a lot of ways, to just kind of ignore it. Not because I thought diabetes would go away. But because trying to manage something you can’t see or measure in any meaningful way is exhausting. Eventually, you stop trying so hard. You just hope the next A1C isn’t too bad.

I eventually found a great doctor. One of those “Best Doctor” award winners. She was thorough, she listened, and her advice was simple: take a fasting glucose reading every morning when you wake up.

Sounds manageable, right?

The problem was that every single morning, the number was higher than it should have been. She told me it should be in the low 100s or below. Mine was consistently in the upper 100s. Or worse. Every morning I’d stick my finger, see a bad number, and start the day already feeling like I was failing.

Looking back, I should have told her it wasn’t working. Should have said, “Hey, this is discouraging and I need a different approach.” But instead I did what I’d always done. I quietly stopped trying and let the problem fade into the background, until the next A1C results came. That wasn’t her fault. She is a great doctor who was giving me sound advice. I just wasn’t ready to have an honest conversation about the fact that I was losing the fight.

And through all of it, I was playing a losing game with willpower. I’d deprive myself of things I enjoyed. Ice cream, carbs, anything that felt like a treat. I’d gut it out for a while, feeling virtuous but miserable, until eventually the willpower would crack. And when it cracked, it didn’t crack a little. I’d overindulge. Then the guilt would set in, and I’d start the cycle all over again. Deprive, resist, break, overdo it, feel terrible, repeat. The whole time, I was cutting out foods that turned out to be perfectly fine for my blood sugar and eating things I assumed were safe that were quietly making everything worse. I just had no way of knowing which was which.

Fast forward to 2024. I’d been hearing ads for continuous glucose monitors on podcasts for months. The pitch was compelling. What predicts lower A1C isn’t random finger sticks. It’s how much time you spend “in range” throughout the day. And a CGM tracks that continuously. A small sensor on your arm. Connected to your phone (and now watch!). Numbers updating in real time, all day, all night.

I talked to my doctor, got a prescription, navigated the insurance maze (they didn’t cover it at first, so I used a discount program until they did), and put the sensor on my arm.

For the first time in twenty years, I felt like I was playing the game with the lights on.

The discoveries came fast.

I’d always been a cereal person in the morning. Loved it. But within days of wearing the CGM, I could see that cereal first thing in the morning sent my blood sugar climbing. Switching to protein in the morning made a visible, immediate difference.

Then came the ice cream experiment.

I’d read an article in The Atlantic about some research out of Harvard. People who ate moderate amounts of ice cream actually showed a slightly lower risk of developing type 2 diabetes. Now, that doesn’t mean ice cream is health food. It was observational data, not proof of anything, and the researchers had plenty of caveats. But the finding stuck with me because it said something I’d never considered: nutrition science doesn’t always work the way you’d assume. And because fat and protein slow down how your body absorbs carbohydrates, ice cream can produce a smaller glucose spike than something like a plain bagel. I didn’t need to take anyone’s word for it, though. I had a sensor on my arm.

I bought a high-quality vanilla bean ice cream. Made myself a small bowl. Ate it slowly. And watched.

No spike. Hardly a blip.

The next night, same thing. Same result.

Meanwhile, a whole wheat bagel in the morning would absolutely wreck me. Certain beers spiked my numbers. Others didn’t. Sourdough toast at 7 a.m. sent my glucose climbing. The exact same slice of sourdough at 3 p.m.? Barely moved the needle.

I learned that pasta at dinner (in reasonable portions) was surprisingly fine. That protein in the morning was non-negotiable. That four Thin Mints (I counted) caused no spike at all. And once I knew what was actually okay, something shifted in how I ate. I didn’t need cheat days anymore. I didn’t need to gorge on a treat because who knows when I’d let myself have it again. If four Thin Mints were fine tonight, four Thin Mints would be fine tomorrow. Moderation got easier when it stopped feeling like deprivation.

This went on for about a year and a half. Constant, quiet experimentation. Every meal was a data point. Every snack was a test. And slowly, the picture of how my body actually worked started to come into focus.

One of the biggest discoveries was something called the dawn phenomenon. Around 4 a.m., my blood sugar starts climbing on its own. It doesn’t matter what I ate the night before. It just happens. My body releases glucose to prepare for waking up, and because I’m diabetic, I can’t process it efficiently.

That single piece of information reframed twenty years of frustration.

All those mornings I stuck my finger and saw a high number? All those times I felt like I must have eaten something wrong the night before? It wasn’t something I did. It was something my body does. Every doctor who told me to test in the morning and aim for a low number was giving me a target I was almost biologically guaranteed to miss.

I can’t overstate how much that changed my relationship with the disease. I went from “I keep failing” to “Oh. So that’swhat’s been happening.”

Around this same time, I started a GLP-1 medication and got more serious about strength training. The weight started coming off. I dropped to the lowest I’d been since high school. And at some point last summer, something shifted. My numbers didn’t just improve. They stabilized. The roller coaster flattened out.

I wanted to understand why. So I did what I’ve been doing more and more lately. I took my data to ChatGPT.

I fed it my workout logs, my scale data, my CGM trends, my lab results. And I asked it to help me figure out what had changed.

The answer was visceral fat. When my body composition shifted enough that my visceral fat dropped past a tipping point, glucose control got dramatically easier. That was the switch. Not a single food change or a single medication. It was a tipping point in body composition that made everything else work better.

That insight motivated me more than any doctor’s advice ever had. Not because the doctors were wrong. But because I could see it. In the data. In the trends. In the way the numbers told a story I could finally read.

AI became something like a personal health analyst after that. I exported my MyFitnessPal logs and uploaded them. I shared lab results and asked questions about individual values. When one marker came back higher than normal, I asked ChatGPT to analyze it in context with my other results. It walked me through why it was likely an isolated abnormal reading and not something to panic about. A few weeks later, I saw a nutritionist who made the exact same dietary recommendations ChatGPT had already given me.

It recommended four supplements based on my bloodwork and goals. I ran them by my clinical pharmacist. She said it was exactly right.

I want to be clear. I’m not replacing my doctors. I’m walking into their offices better informed, with better questions, and with a clearer picture of what’s actually going on. When I had surgery a couple of years ago, the hospital put me on their standard “diabetic diet.” It included pudding and graham crackers. My blood sugar spiked constantly, and they gave me insulin to manage the spikes their own menu was causing. They weren’t doing anything wrong by the book. But the book doesn’t know my body. The real power is in the data. The CGM, the nutrition logs, the health metrics from my watch. That’s the foundation. AI just helps me connect the dots, spotting patterns across months of information that I’d never piece together on my own.

After nearly two decades of managing this disease blindfolded, I posted back-to-back A1Cs of 6.6 and 6.5. Not through white-knuckling it. Not through deprivation or willpower. Through understanding.

And now that I’m in the zone, something funny has happened. I don’t obsessively check the CGM anymore. For almost two years, I watched it constantly. Every meal, every snack, every morning. But staying in range comes naturally now. I check in occasionally to make sure I’m still on track, the way you’d glance at a GPS when you already know the route. Diabetes isn’t something I ignore anymore. But it also isn’t always present in my thoughts. The anxiety is gone.

A sensor that costs less than a dinner out can show you, in real time, how your body responds to what you eat. An AI can take months of that data and help you see patterns you’d never catch yourself.

You just have to be willing to look at the numbers. And then let the numbers show you what to do next.

We flew home on a red-eye through Phoenix, landed in Charlotte on Monday afternoon, and walked back into our normal lives.

The trip was over. But I kept thinking about how it had come together.

Not just the places we’d stayed or the things we’d done, but the process of planning it. How different it felt from every other trip I’d planned before.

I’ve always been a planner. Always done the research myself. And for years, that meant drowning in information.

Open twenty tabs. Read conflicting reviews. Fall down rabbit holes on Reddit. Spend three hours comparing hotels and end up more confused than when I started. The internet gave us access to everything, but it never helped us decide. It just gave us more reasons to second-guess ourselves.

This time felt different because planning wasn’t about gathering information. It was about having a conversation.

I’d tell ChatGPT what we wanted... adventure and relaxation, hiking and beaches, something that felt special for a milestone anniversary. And instead of dumping a list of links at me, it would ask questions back.

How long are you thinking?
Do you want to start with the active part or save it for the end?
You mentioned you like less crowded places... does that apply to lodging too, or just activities?

It remembered what I’d said three weeks earlier and used that context to shape suggestions now. It didn’t just answer my questions... it helped me ask better ones.

And slowly, through that back-and-forth, a plan emerged that made sense. Not because AI made the decisions for me, but because it helped me think more clearly about what I actually wanted.

Here’s what AI did for this trip:

It synthesized information I never could’ve processed on my own. Every article, every review, every forum post, every guidebook. It had access to all of it and could pull out the relevant pieces without me having to read hundreds of pages.

It asked follow-up questions that forced me to clarify what mattered. When I said I wanted a “White Lotus vibe” for the resort, it didn’t just guess. It asked what that meant to me and used the answer to narrow down options.

It helped with logistics in ways that saved hours of work. The anniversary drive from Volcano to the Fairmont? I told it what time we could leave and what time we needed to arrive, and it mapped out a route with lunch and waterfalls that hit the timing perfectly.

It was always there. On the trip itself, we used ChatGPT and Perplexity constantly. Identifying flowers and birds, answering random questions about how cruise ships store their tenders, checking sunset times for our anniversary dinner, even helping us decode weather forecasts when we needed to figure out which beach to hit.

But here’s what it didn’t do:

It didn’t book anything. I still had to go to hotel websites, compare photos, read cancellation policies, and click “reserve.”

It didn’t make the final calls. I decided the Fairmont was worth the extra money. I decided we should do Volcano first. I decided to book the manta ray tour even though I had no idea what I was signing up for.

It didn’t replace the experience. The tools helped us get there and stay organized, but they didn’t hike the Kīlauea Iki crater for us. They didn’t float in the dark Pacific with rays gliding underneath. They didn’t watch the sunset from Brown’s Beach House.

The trip still required us to show up, make choices, and be present for the moments that mattered.

What changed wasn’t the destination or even the itinerary.

What changed was how I felt during the planning process.

Usually, planning a big trip fills me with low-level anxiety. Did I pick the right hotel? Should I have spent more time researching activities? Did I miss something better? The decisions never feel confident. They just feel like the best I could do with limited time and too much information.

This time, I felt confident. Not because AI told me I’d made the right choices, but because the process itself felt more thoughtful. I wasn’t just reacting to whatever popped up first in a Google search. I was thinking through trade-offs, asking questions, iterating over time.

By the time we boarded the plane, I wasn’t second-guessing anything. I wasn’t lying awake wondering if we should’ve stayed somewhere else or structured the trip differently.

I felt ready. Excited. Sure that the plan made sense for us, not just for some generic traveler reading a “Top 10” listicle.

There’s a bigger shift happening here, and it’s not just about travel.

For years, the internet gave us access to infinite information but no help making sense of it. Search engines pointed us toward answers, but they didn’t help us think. We had more options than ever and less clarity about which ones actually mattered.

AI changes that. Not by making decisions for us, but by helping us have better conversations with ourselves about what we actually want.

It’s not a replacement for judgment. It’s a tool for thinking more clearly.

And that’s what I didn’t expect when I opened ChatGPT back in March and asked about the weather in Mauritius. I thought I was looking for information. What I found was a way to organize my thinking that didn’t bury me in tabs and reviews and endless second-guessing.

The trip was incredible. The Volcano Village Lodge exceeded every expectation. The Fairmont gave us exactly the kind of relaxing, open-air resort experience we’d hoped for. The manta rays were terrifying and magical. The snorkeling at that beach north of the resort might’ve been my favorite hour of the whole trip.

But more than any individual moment, what I’ll remember is how the whole thing felt.

It felt like we’d made a plan that actually fit us. It felt like we’d committed to something and followed through without constantly wondering if we’d made the wrong call. It felt like we’d celebrated twenty-five years of marriage in a way that honored both who we are now and the adventures we still want to have.

And it felt possible because planning didn’t feel like drowning anymore.

So yes, I’ll use AI for future trip planning.

Not because it’s perfect or because it removes all the work. But because it changes the nature of the work from exhausting to collaborative. From paralyzing to clarifying.

The next time I need to plan a trip, I’ll skip the tabs and the endless reviews and the Reddit rabbit holes. I’ll open a conversation instead of a search engine.

I’ll start by asking a simple question.

And I’ll trust that the process (the back-and-forth, the clarifying, the iterating) will lead me somewhere worth going.

End

Thanks for reading this six-part series about planning a trip to Hawaii with AI. If you’ve ever felt overwhelmed by travel planning, or any kind of planning, I’d love to hear how you’ve approached it. Hit reply or leave a comment.

And if you’re thinking about trying AI for your next trip, my advice is simple: don’t ask it to plan the trip. Ask it to help you think about what you actually want. The rest will follow.

We arrived at the Fairmont Orchid after our drive from Volcano and tour up the eastern coast with just over an hour to spare before dinner. We’d made the reservation at Brown’s Beach House weeks in advance, timed specifically for sunset.

ChatGPT had helped with that timing... not just picking a restaurant, but figuring out when the sun would actually set so we could request a table at the right time. Brown’s Beach House sits right on the water, and we got a table up front, closest to the beach.

The sun dropped slowly over the ocean, painting everything gold and orange. Torches were lit along the pathways. The pū ceremony began... a conch shell blown to mark the sunset, a small ritual the resort did every evening. We sipped our cocktails and watched it all unfold.

I ordered that night’s special... ti leaf-steamed local fish, opened tableside with a light coconut-ginger sauce, paired with island fried rice. Nicole went with the macadamia nut-crusted local fish, one of Brown’s signatures. We shared a bottle of Penner-Ash Pinot Noir.

For dessert, they brought us crème brûlée topped with pineapple and whipped cream, complete with a tiny sign wishing us a happy anniversary.

It was the splurge meal. The one we’d been planning toward. And it was perfect.

This was the moment the entire trip had been building toward... twenty-five years, and here we were, watching the sun set over the Pacific, exactly where we were supposed to be.

Wednesday morning started early. The six-hour time difference with home meant we were wide awake by 6 a.m., which worked out perfectly since we’d booked an outrigger canoe and snorkeling tour for 7:30.

Just us and a guide.

But the night before, I’d tried to set up the GoPro and realized: no SD card. We’d bought the camera and all the accessories back in Hilo, but I’d completely forgotten the one thing that actually makes it work!

So the next morning, we met our guide at the beach knowing we’d have to make a Target run afterward if we wanted any underwater footage for the rest of the trip.

The canoe was modern but built in the traditional style... sleek, stable, with an outrigger on one side. Our guide sat in back, steering and telling us about growing up on the island, fishing with his family. He mentioned a school trip to Volcano when he was younger, but said that area was way too cold for him. He was a coast guy through and through.

We paddled south along the coast, past other resorts and rocky shoreline, until we reached a small bay.

He tied us to a mooring buoy and we slipped into the water.

This was why we’d brought our own snorkeling gear. The masks fit better. The fins were longer, which meant we could move through the water without working as hard. And we could see everything clearly.

The water was mostly clear except for pockets where freshwater flowing through lava tubes from the mountains mixed with the salt water. You could feel it immediately when you hit those spots... suddenly much colder.

We saw schools of bright yellow tangs, parrotfish, triggerfish, and some kind of ray gliding along the bottom. Our guide pointed out coral formations and explained which fish were native and which had been introduced.

After about forty-five minutes, we climbed back into the canoe and paddled back to the resort. He gave us recommendations for lunch spots in Kona... good local places, not tourist traps... and we thanked him and headed back to the room to change.

Time for the Target run.

We drove back to Kona, found the other Target, and finally bought the SD card. Nicole pointed out that we’d now been to all the Targets on the Big Island! It felt like a weird accomplishment, but we were claiming it anyway.

Then we stopped at Umekes Fish Market Bar & Grill for fish tacos, exactly as our guide had recommended.

They were excellent.

We got back to the resort mid-afternoon and I finally got to test the GoPro in the water. I swam around the resort beach, filming fish and coral and getting used to the controls. The footage looked great. I felt vindicated for the two-Target odyssey.

That evening we grabbed a table at the Hale Kai... the poolside bar and restaurant right next to Brown’s Beach House. Another front-row seat for the sunset. Another pū ceremony as the torches were lit. Another perfect end to the day.

Then it was off to swim with the Manta Rays.

Thursday morning, we were up early again.

We’d booked a stand-up paddleboard tour that took us out of the protected lagoon at the resort and into the open ocean. Just us and a guide who talked the entire time... and I mean the entire time. Island history, family stories, reef ecology, fishing techniques, weather patterns. He also mentioned a school trip to Volcano years ago, and like the canoe guide, said it was way too cold up there for him. He was enthusiastic and knowledgeable and didn’t stop for almost two hours.

It was a lot of information. But it was fun, and paddling in the open ocean felt like an accomplishment.

The rest of Thursday was spent at the pool, reading and swimming and finally just being still.

We’d been tracking the weather forecast for Mauna Kea all week, hoping for a clear night to drive up to the Visitor Information Station for stargazing. At 9,200 feet elevation, it’s supposed to be one of the best accessible stargazing sites in the world. But the observatory’s weather page read like it was written for meteorologists... cloud coverage percentages, atmospheric stability indices, wind speeds at different elevations. I kept feeding the updates to ChatGPT, asking it to translate: Is this worth the two-hour drive or not?

Every day, the answer was some version of: probably not.

We could see Mauna Kea from the resort, but we could never see the top. The clouds just weren’t cooperating. By Thursday evening, I checked one more time. ChatGPT’s analysis was clear: the summit forecast showed near-total cloud cover with no improvement expected. We’d have driven two hours up a winding mountain road in the dark to stare at fog.

So instead, we had dinner after sunset at the Luana Lounge, which sits on a balcony overlooking the resort grounds. A mai tai. An evening where we didn’t have to think about logistics or schedules or what came next.

Friday was a beach day.

We rented a covered daybed and spent most of the day reading, swimming, and letting the hours disappear. We did our own snorkeling off the resort beach and saw more fish... and a moray eel tucked into the rocks, just its head poking out. The water wasn’t as clear as it had been during the guided tour, but it was still good enough to enjoy.

The resort had a rhythm to it by now... early coffee for me and tea for Nicole with açaí bowls by the beach, mid-morning in the water, lunch delivered to wherever we’d set up camp, afternoon naps, sunset drinks, dinner somewhere on the property.

It felt exactly like what we’d needed after the hiking and driving and constant movement of the first half of the trip.

Saturday morning, one of the pool attendants we’d been chatting with all week gave us a recommendation.

“If you walk north on the beach trail, past the resort boundary, there’s another beach about ten minutes away. The snorkeling there is even better than here. Crystal clear water. Lots of coral. And you’ll probably see turtles.”

We grabbed our snorkeling gear and followed the trail.

He was right.

The water was the clearest we’d seen the entire trip. The sunlight hit it perfectly. The coral was vibrant. And within a few minutes, we saw a sea turtle just hanging out near the rocks, coming up for air and then diving back down to graze on algae.

We watched him for a while, keeping our distance, just floating and observing.

Then we swam out toward deeper water... toward what looked like a drop-off where the ocean floor suddenly fell away. In Finding Nemo, they call it “the drop off.” That’s what this felt like. You’re swimming along in maybe twenty feet of water, and then suddenly there’s nothing below you but deep blue emptiness.

It was beautiful and a little unsettling at the same time.

I went back out by myself later that afternoon and found another turtle. This one let me follow him for a while as he surfaced for air, dove back down, and munched on algae growing on the rocks.

I stayed out there longer than I meant to, just watching. It felt like the perfect way to end our time in the water.

That night was the resort’s luau.

Traditional Hawaiian food... kalua pork, poi, lomi salmon, haupia for dessert. Cultural performances with hula dancing, fire dancing, and storytelling about Hawaiian history and traditions. We sat at a long table with other couples and families, chatting and laughing and enjoying the show.

It was touristy, sure. But it was also genuinely fun. And it felt like a fitting way to spend our last night at the resort.

Sunday morning, we watched the sunrise over the mountains one last time... me with coffee, Nicole with tea... by the pool. Then we walked south on the beach trail to see the historic Hawaiian fish ponds... stone-walled enclosures where ancient Hawaiians had figured out how to create a mix of salt and fresh water. Young fish would swim in through small openings to feed, then grow too large to escape.

It was a small thing, but it felt like a fitting bookend to the trip... seeing one more piece of history before we left.

We packed up, checked out, and loaded the car.

Our flight didn’t leave until 10 p.m., so we had a full day to explore the southern part of the island. We used the GuideAlong app again, stopping at scenic overlooks and little towns along the way. We had lunch at the southernmost restaurant in the United States and bought pastries at the southernmost bakery in the United States.

Then we drove back to Kona to explore the downtown area and buy souvenirs.

We found a restaurant overlooking the water and sat down for our last Hawaiian meal. A large cruise ship sat offshore, and we watched the tenders ferry passengers back and forth between the ship and the dock.

I wondered out loud where they stored those tenders when the ship was at sea.

Nicole laughed. “Just ask Perplexity.”

So I did.

Turns out the Celebrity Edge stores its tenders in special compartments built into the sides of the ship... recessed alcoves on Deck 2 with shell doors that open to deploy them. The “Magic Carpet,” a moving platform on the ship’s side, can raise and lower to help with tender operations. The design keeps the tenders protected from the elements and makes loading passengers more efficient.

It was one of many random questions we’d asked ChatGPT or Perplexity throughout the trip... identifying plants and birds, figuring out routes, looking up historical details, decoding weather forecasts. Just having that tool available in your pocket changes how you experience things. You don’t have to wonder. You can just know.

The sun set one last time. The tenders kept shuttling. And we sat there soaking in the last hour of the trip before heading to the airport.

Next: Part 6 - What It All Means (or: how planning became a conversation)

The thing about trust is that it builds slowly, one decision at a time.

The drive from Volcano Village to the Fairmont Orchid on the Kohala Coast takes just about two hours without stops, but it doesn’t feel like that. It feels like crossing through three or four different worlds, each one surprising in its own way.

We left Volcano in the morning on our anniversary. ChatGPT had laid out the route the night before: north through Hilo, up the Hamakua Coast, with a couple of stops that would turn a straight drive into something worth remembering.

The first stop was Rainbow Falls, right in Hilo. A quick pull-off, a short walk, and there it was... an eighty-foot waterfall plunging into a pool surrounded by lush jungle. We stood there for ten minutes, took some photos, then kept moving.

From there, we drove into downtown Hilo for lunch. Just as we sat down outside under the lanai at Hilo Bay Cafe, a woman leaving leaned over our table on her way out and said, unprompted, “The crab cake salad is to die for.”

She was right. Best crab cake salad I’ve ever had.

We sat overlooking Hilo Bay, watching the water and Mauna Kea rising in the distance, planes arriving from the other islands at the airport nearby. It was the kind of lunch that felt like it belonged in the trip... not rushed, not touristy, just right.

After lunch, we got back on the road and headed up the Hamakua Coast. This is where I pulled out the GuideAlong app again, the same GPS-based audio tour we’d used at Volcanoes National Park. The voice narrated through the car speakers as we drove, pointing out landmarks, telling us the history of the area, flagging scenic lookouts where we could pull over if we wanted.

One of those stops was Akaka Falls. We parked and hiked the short loop trail through thick jungle. The path led to a viewpoint where you could see the waterfall... 442 feet, dropping straight down into a gorge surrounded by green so thick it looked fake. We stood there, watched the water fall, listened to the roar, then walked back to the car.

The drive continued north, the landscape shifting again. The jungle thinned out. Rolling green hills appeared. Pastures. The GuideAlong narrator told us about the ranching history of the area near Waimea, how Hawaii has had cowboys and cattle ranches for nearly two centuries. I had no idea.

It felt surreal. We were still in Hawaii, but the landscape looked nothing like what we’d imagined. Open pastures. Rolling hills. This could’ve been Montana.

Photos: Views from our drive up the Hamakua Coast.

As we got closer to the coast, the landscape slowly transitioned back. The green faded. The black lava fields returned, stark and dramatic against the ocean.

By the time we pulled into the Fairmont Orchid’s entrance, we’d seen waterfalls, jungle, ranches, lava fields, and coastline. The drive hadn’t just been a way to get from one place to another. It had been part of the trip.

But as we turned onto that long, manicured driveway (tropical landscaping, perfectly trimmed hedges, valet parking), Nicole and I both felt it at the same time.

“This feels... different,” I said.

We’d just spent three nights at Volcano Village Lodge, this cozy, intimate place where breakfast was delivered to your room and the only sound at night was rain on the roof. This was bigger. More polished. The kind of place where you could imagine conference rooms tucked away somewhere behind the lobby (there were).

Corporate.

I felt a flicker of doubt. Had we made the wrong call?

Then we checked in. Walked through the property. Found our room.

And I realized: ChatGPT had been right.

The Fairmont wasn’t trying to be Volcano Village Lodge. It wasn’t supposed to be cozy and tucked away. It was open, spacious, restorative in a completely different way. Our room had a view of the ocean and the golf course. Nothing to write home about, really. The room was nice, but it wasn’t the room that made this place special.

It was everything else.

The beach was steps away: calm, swimmable, lined with lounge chairs but never crowded. There was a quiet pool surrounded by gardens. Everything felt designed for one thing: slowing down.

This was exactly what we needed after the intensity of the volcano and the long drive. A place to breathe. To sit. To not do much of anything.

The doubt we’d felt in the driveway evaporated.

By this point in the trip, I’d stopped questioning whether the AI planning would pan out. Volcano Village had been perfect. The Fairmont was perfect in a completely different way. This wasn’t luck anymore. This was actually working.

Photos: Various spots on the Fairmont Orchid property.

The manta ray night snorkel had come up early in the planning. ChatGPT mentioned it as one of the “must-do” experiences on the Big Island, tucked into a longer list of activities. Nicole latched onto it immediately. She brought it up several times in the weeks before the trip, each time with a little more excitement.

I didn’t overthink it. It sounded amazing. Unique. The kind of thing you can’t do anywhere else.

So I booked it.

I didn’t fully understand what I was signing up for.

Here’s what it actually looks like:

Twenty-four of us, all in wet suits, loaded onto a rigid inflatable boat (the kind military special forces use). The boat is called the Orca. That should’ve been a clue.

We speed out into the dark Pacific for at least fifteen minutes, though it feels longer. The ocean is black. The boat slams over waves. The engine roars. We sit facing outward, holding on, wind and salt spray hitting our faces.

It’s terrifying and exhilarating at the same time. Like we’re on a Navy SEAL mission instead of a tourist activity.

When we finally stop, the guides give us instructions: hold onto the floating platform, face outward, keep your arms and legs still. The lights below will attract the mantas. Just float. Just wait.

But first, we have to get in.

We’re sitting on the gunwale of the boat, wet suits on, the dark Pacific stretching out in every direction. The guide tells us to drop into the water. I look down. I can’t see anything. Just black.

I force myself not to think. Just go.

I push off and drop.

The water is warm. Warmer than I expected. I surface, grab the platform next to Nicole.

Then we’re floating. Looking down into darkness. Waiting.

It’s one thing to understand the concept intellectually: mantas eat plankton, plankton are attracted to light, so we float above the lights and the mantas come to feed. It’s another thing entirely to be in the open ocean at night, looking down into darkness, waiting for something massive to appear below you.

The first manta I see is enormous. Fifteen feet across, maybe more. It glides up from the deep, silent and weightless, wings moving in slow, hypnotic waves. It sweeps just below me, close enough that I could reach out and touch it (though we’re told not to).

Then another one. And another.

They’re everywhere. Circling. Rising. Feeding. Moving with a grace that doesn’t seem possible for something that size. I can see their white underbellies, their gaping mouths filtering plankton from the water, their dark eyes reflecting the lights.

It’s beautiful. It’s surreal. It’s also still a little terrifying.

I glance over at Nicole. She’s mesmerized, her face half-submerged, watching a manta glide directly beneath her. I can see it in her eyes through the mask: the same mix of fear and awe I’m feeling.

For the next forty-five minutes, we just float there. Witnessing something most people will never see.

On the boat ride back (just as wild, but with the brilliant stars filling the dark sky above us, it felt almost peaceful), Nicole looked at me.

“I didn’t realize that’s what we signed up for.”

“Neither did I,” I said.

She laughed, and I did too. The kind of laugh that comes after you’ve done something terrifying and survived it and can’t quite believe it happened.

If I’d known exactly what the experience would be like (how dark the water would be, how big the mantas were, how exposed I’d feel), I might have talked myself out of it. Nicole might have, too. But we didn’t know. We just trusted the recommendation. Booked it. Showed up.

Here’s the thing I’m realizing: I’m not sure we’d do it again. It was that intense. But I’m so glad we did it. It pushed me outside my comfort zone in a way I didn’t expect. And now we’d done something unforgettable.

That’s the paradox of trust. Sometimes the best experiences are the ones you wouldn’t choose if you knew exactly what they’d be like.

Back at the Fairmont that night, sitting on the balcony with the sound of waves in the background, I realized something:

I’d stopped thinking about the planning.

I wasn’t analyzing whether ChatGPT’s suggestions were working out. I wasn’t second-guessing decisions or wondering if we should’ve done something differently. I was just here. Living the trip we’d planned.

The tool had done its job. It helped me narrow options, think through logistics, and make informed choices. But now it was out of the way. I wasn’t thinking about AI. I was thinking about manta rays. About the way Nicole’s face lit up at the volcano. About rainforests and waterfalls and cowboy country and crab cake salad and coffee in an Adirondack chair overlooking the Pacific.

Good tools don’t demand attention. They help you make decisions, then they disappear so you can live the life you chose.

The next morning, we woke up early. Went down to grab coffee for me, tea for Nicole. Then we walked out to the ocean and sat.

The water was calm. The sky was just starting to lighten. Somewhere out there, mantas were still gliding through the water, feeding in the dark.

I’d almost doubted this place. Almost questioned whether we’d made the right call.

But we had.

And I was learning to trust that.

Next: Part 5 - Where We Finally Stop Moving

Photo: View from Saddle Road heading toward Hilo.

We landed in Kona around 2 p.m., picked up our rental Ford Explorer, and started the drive east across Saddle Road.

Saddle Road cuts straight across the middle of the Big Island between two massive volcanoes: Mauna Kea to the north, Mauna Loa to the south. For most of the drive, you’re surrounded by barren lava fields that stretch in every direction, black and rust-colored rock as far as you can see. It looks like Mars.

Then you crest a ridge, and the landscape starts to shift. Green appears. Trees. Clouds hanging low over the hills. It gets greener as you go, but it’s not until you turn off the main road into Volcano that it hits you… thick, lush, impossibly green rainforest pressing in from all sides.

We’d been awake for nearly twenty hours, running on airport coffee and tea and the adrenaline of finally being here. Volcano is barely a town… a handful of restaurants, a gas station, a brewery, and not much else. We turned off the main road onto a tree-lined street, then into a gravel lot tucked back from the road. A gravel path led us deeper into the property toward the office.

The Volcano Village Lodge sat at the end of that path, tucked into the forest like it had grown there.

Photos: Volcano Village Lodge path to office & Nicole and me wearing our leis.

A woman greeted us at the main office with leis… fresh flowers draped over our shoulders… and led us up a path through the trees to our cabin.

I thought I’d booked a room.

Turns out I’d booked an entire cabin.

When I reserved the “Kilauea,” I assumed it was a class of room, like booking a “deluxe king” at a hotel chain. But there were only five cabins on the entire property, each one named after a different volcano. We had the Kilauea cabin. Just us. Surrounded by rainforest.

She opened the door and handed us the key.

Three walls of the cabin were almost entirely glass. Beyond them: rainforest so dense you couldn’t see or hear anything beyond it. No neighboring properties. No roads. No signs of civilization. Just thick green foliage pressing in from every direction, creating a cocoon of complete privacy.

There was a king bed facing the windows. A gas fireplace. A mini fridge, coffee maker, teapot, and microwave tucked into a corner. The room itself was rustic… clean and comfortable. But that wasn’t the point. The point was the view, the atmosphere, the feeling of being wrapped in rainforest. And scattered around the property, quiet spots to wander… cushioned chairs, porch swings, places to sit and disappear into the trees.

Photos: Views and amenities at the Volcano Village Lodge.

Nicole walked straight to the windows and just stood there.

“This is unreal.”

I opened the fridge. Inside: a homemade frittata wrapped in foil, a fresh fruit plate with pineapple and papaya, and orange juice.

No packaged sandwich. No sad continental breakfast. Actual homemade food left for us like we were staying at someone’s home.

The bed had electric mattress warmers… two separate controls so we could each set our own temperature. There was a basket with trail snacks and a flashlight in case we wanted to walk the grounds after dark.

Everything about this place exceeded expectations in quiet, thoughtful ways.

Score one for ChatGPT. This was the lodge it had recommended early on, and I’d just gone with it. No overthinking, no second-guessing. And it nailed it.

We went to sleep that night to the sound of frogs. Woke up the next morning to birds singing and soft light filtering through the trees.

Photos: Scenes from our 15 mile hike through Volcanoes National Park.

Hawai’i Volcanoes National Park is two miles from the lodge.

We spent two full days there, hiking just over fifteen miles total across landscapes that felt like walking on another planet.

The Crater Rim Trail follows the edge of Kilauea’s caldera, over two miles wide, with steam vents hissing along the path. The ground is warm in spots where heat from below breaks through. And in the distance, you can see the evidence of the most recent eruption, which had started and ended just two days before we arrived. The lava lake was cooling, still glowing faintly at night, but during the day it just looked like fresh black rock.

The highlight, though, was the Kīlauea Iki Trail.

Kīlauea Iki means “Little Kilauea,” and it’s a smaller crater formed during a 1959 eruption. The trail descends through rainforest, switchbacking down the crater wall until you reach the floor… a solidified lava lake nearly a mile across.

Walking across it feels surreal. The ground is uneven, cracked, jagged in places. You follow cairns, which are stacks of rocks that mark the trail across the blackened surface.

And all around the edges of the crater, the rainforest has started reclaiming the land. Ferns grow in crevices. Small trees push up through the lava. It’s this strange, beautiful contrast… life slowly taking back what the volcano destroyed.

We stopped in the middle of the crater and just stood there. No one else around. Just us, the rock, and the quiet knowledge that we were standing on what had been molten earth just decades ago.

Nicole looked at me. “This is worth it.”

I knew she wasn’t just talking about the hike.

All day long, we kept seeing signs about the nēnē, Hawaii’s state bird, endangered and protected. *Please don’t feed the nēnē. Watch for nēnē crossing.* We hadn’t seen one yet.

So every bird we spotted, I pulled out my phone, snapped a photo, and uploaded it to ChatGPT. *What is this?*

Kalij pheasant.

We kept walking.

This became our rhythm. One of us would spot something… a bright flower, an unusual plant, a bird we didn’t recognize… and I’d take a photo and ask. The answers came back fast.

Red anthurium.

White anthurium.

Kahili ginger.

Bamboo orchid.

We were learning the rainforest whether we meant to or not.

Then, walking back to the car after one of the hikes, Nicole spotted a cluster of birds on the grass that looked different. Stocky. Goose-like. I pulled up my phone, snapped the photo, uploaded it.

Nēnē (Hawaiian goose). Hawaii’s state bird.

We stood there grinning like we’d won something.

It wasn’t about collecting facts. It was about feeding curiosity the moment it showed up. See something. Wonder about it. Know. And then notice more because of it.

Photos: Lunch and snacks in the park.

The lodge packed us lunch both days… ham and turkey sandwiches, water, guava drinks, trail mix, and cookies in a reusable insulated bag. That first day, we found a picnic table under the trees and ate while comparing notes on what we’d seen so far… the best views, the weirdest steam vents, how our legs were already feeling the miles.

On the second day, after we’d hiked the Thurston Lava Tube and the short Devastation Trail, we drove down to the coast on the Chain of Craters Road. This is where I remembered the GuideAlong app.

I’d used it years ago at Yellowstone… an audio tour that plays through your car speakers and tells you what you’re seeing as you drive using GPS. I pulled it up on my phone, saw they had a Big Island tour, and bought it on the spot.

As we drove, a voice narrated the landscape through the car speakers: how the lava flows reached the ocean, why certain areas were roped off, where to stop for petroglyphs carved into the rock centuries ago. It was the kind of tool that made you notice things you would’ve driven right past, but it didn’t control the experience. We stopped where we wanted. Skipped what didn’t interest us. Paused the audio when we wanted quiet.

It was everything a tour bus isn’t. We got the context without giving up the freedom.

Photos: Stops along the Crater Rim Drive.

We stopped at the petroglyphs and hiked a short, hot trail over jagged lava rock to see these ancient carvings… simple figures etched into stone by people who lived here long before any of this became a national park.

Then we drove down to the coast, where black lava meets turquoise water. It was too windy to sit outside comfortably, so we ate our packed lunch in the car, windows cracked, watching the waves crash against the rocks.

On the way back, we stopped at the Volcano House… the historic lodge inside the park that sits right on the rim of the caldera. ChatGPT had mentioned it as one of the lodging options early on. We grabbed a couple of beers and sat in the bar with a direct view into the crater.

The views were stunning. The beer was cold. But the place had clearly seen better days… a hotel that happened to be on the rim of a volcano but felt past its prime. I was glad we’d picked the lodge instead… a place that felt like it belonged in the forest, not just near it.

Our last night in Volcano, we had dinner at the Thai Thai Bistro & Bar, a little spot in town.

That night, back at the cabin, I pulled out my phone and opened ChatGPT.

We’d be leaving Volcano in the morning, heading to our resort on the Kohala Coast. The question was: which route? The southern route was faster, straight across the island, back through the lava fields. The northern route went through Hilo and up the coast, but added time and stops.

I asked ChatGPT: *Is Hilo worth it?*

It laid out both options. The southern route: efficient, familiar terrain. The northern route: Rainbow Falls, Akaka Falls, scenic lookouts along the Hamakua Coast, a different side of the island.

It recommended north.

I told it we wanted to arrive at the resort by 4:30 and what time we’d be leaving Volcano. I also mentioned we’d want lunch on the water if there was a good option in Hilo.

It built the day: Rainbow Falls first (quick stop, right in Hilo), then lunch at a spot on the bay, up the Hamakua Coast to Akaka Falls (short hike, worth the detour), with a couple of scenic lookouts flagged along the way.

Clean. Flexible. Enough structure to follow, enough space to skip things if they didn’t feel right.

I saved the plan and put my phone down. Tomorrow would be different… more movement, more stops, less quiet. But I was ready for it.

We went to bed that night full, tired, and grateful.

The next morning, our anniversary, we reheated one last frittata and ate it at the small table overlooking the rainforest. Twenty-five years. We didn’t say much about it. Didn’t need to. The trip itself was the thing we were saying to each other.

We packed our things and stood on the deck for a few minutes just looking out at the trees.

Three nights wasn’t long enough. But it was exactly what we needed… a quiet, grounding start to the trip before we transitioned to the coast.

We loaded the car and headed north toward Hilo. I didn’t know exactly what was coming next, just that it would be different. Volcano had been quiet, grounding, exactly what we needed. Now we were heading toward the coast, toward people and activity and the second half of the trip. I was ready for it. But I was also glad we’d started here, in the trees, with nothing to prove and nowhere else to be.

Next: Part 4 – I Had No Idea What We’d Signed Up For

Photo: View from the lobby of the Fairmont Orchid

Here’s what planning a trip usually looks like for me:

Open Google. Type something like “best places to stay in Hawaii.” Click the first three articles. Open TripAdvisor in another tab. Start reading reviews. Someone loved the hotel. Someone hated it. Someone says the beach is perfect. Someone says it’s too rocky. Open another tab for flights. Check prices. Get distracted by a different island. Open a Reddit thread from 2019. Read seventeen conflicting opinions about whether September is too rainy.

Three hours later, I have forty-two tabs open, a vague sense of information overload, and no actual decisions made.

This time felt different from the start.

The real work happened in the in-between moments, during planning and throughout the trip itself.

Once we’d settled on the Big Island and the basic structure… adventure first, resort second, the conversation shifted from “what” to “how.” And that’s where things got interesting.

I’d ask a question. ChatGPT would answer it. Then it would ask a follow-up question I hadn’t thought about.

What’s the best route from Volcano to the Fairmont?

It gave me two options: the southern route along Highway 11 (the way we’d drive in from Kona) or the northern route back through Hilo and up the coast.

Then: You’ll already be driving through the southern part on the way in. Do you want to see something new on the way to the resort, or would you rather take the faster, more direct route?

I paused. I hadn’t thought about it that way. Of course I wanted to see something new.

What’s worth seeing on the northern route?

Rainbow Falls. Akaka Falls State Park. The scenic coastline. Cowboy country near Waimea… yes, Hawaii has cowboys and ranches. Then it asked what time we needed to check in at the resort and worked backward to build a timeline, including a lunch stop at Hilo Bay Cafe.

This wasn’t just answering questions. It was helping me design the day in a way that made sense… not rushed, not wasting time, just right.

That happened over and over. I’d ask about activities, and it would flag logistics I hadn’t considered. I’d mention wanting to snorkel, and it would suggest bringing our own gear instead of using resort equipment because the fit and quality would be better. I’d ask about stargazing at Mauna Kea, and it would check the weather patterns for late September and tell me we’d likely need a backup plan because cloud cover was common that time of year.

It wasn’t doing the thinking for me. It was doing the thinking with me.

The lodging choices forced me to get honest about what we actually wanted.

For Volcano Village Lodge, the decision was easy. Private cabins in the rainforest with fireplaces and views… it matched exactly what I wanted for that part of the trip. The photos looked perfect. I booked it.

The beach resort was harder.

When I said I wanted something that felt like season one of The White Lotus… open-air, everything blending indoors and outdoors… ChatGPT gave me a list of nine hotels in three tiers: luxury, midrange, budget.

I clicked through all of them. The Fairmont Orchid kept pulling me back. The beach looked perfect. The photos matched the vibe I wanted. But the price made my stomach hurt.

I kept going back to the OUTRIGGER Kona Resort. Nice. Well-reviewed. A lot cheaper. I’d look at the Fairmont, feel my stomach clench, then click back to the OUTRIGGER and think, This is fine. This is totally fine.

Finally, I asked ChatGPT directly:

Am I being ridiculous spending this much on a hotel when the OUTRIGGER looks perfectly fine?

It didn’t hype me up or tell me to treat ourselves. It gave me a framework:

The Fairmont offers a larger property, a better beach for snorkeling, more on-site dining, and a more “destination resort” feel. The OUTRIGGER is great if you’re planning to spend most of your time off-property exploring. Since you’re planning to relax at the resort for five days after hiking, the Fairmont might be worth it. But if budget is a concern, you’ll be happy at the OUTRIGGER too.

That helped me realize what I was actually deciding: Was this trip about checking boxes and seeing sights, or was it about creating a specific feeling for our 25th anniversary?

The Fairmont wasn’t just a hotel. It was the place where we’d slow down, decompress, watch sunsets, and not think about logistics for five straight days.

We booked it. And I stopped second-guessing.

Then came the activities I didn’t know I wanted.

I knew we’d snorkel. I figured we’d do some beach time. Maybe a hike or two outside the national park. Standard stuff.

But ChatGPT flagged things I’d never heard of.

Have you considered a guided outrigger canoe and snorkeling tour? The Fairmont offers one that’s intimate… just you, your partner, and a local guide. You paddle out together and snorkel in a less crowded bay.

That sounded perfect. Booked.

There’s also nighttime snorkeling with manta rays off the Kona coast. Tour operators use UV lights to attract plankton, and the manta rays come up to feed.

That sounded cool. I pictured small rays in a calm bay close to shore. Something peaceful and magical. I booked it without looking too deep into the details.

I had no idea what I’d actually signed us up for.

None of these were things I would’ve found through normal research. They weren’t on the top of Google results. They weren’t in the “Top 10 Things to Do” listicles. They emerged through conversation… because I’d been feeding ChatGPT context about what we liked over weeks, and it was connecting dots I wouldn’t have connected on my own.

There were also things it couldn’t do.

It couldn’t book anything. I still had to go to hotel websites, read cancellation policies, compare photos, and click “reserve.” It couldn’t tell me whether the Fairmont was objectively worth the money… it could only help me think through what mattered to us.

It couldn’t make the manta ray decision for me. That was a leap I had to take on my own.

And it couldn’t tell me if the trip would actually work… if the pacing would feel right, if the itinerary would hold up in real life, if the places would live up to the descriptions.

But here’s what it did do: It processed more information than I ever could… every article, every review, every forum post, every travel guide… and synthesized it into something I could actually use. It remembered what I’d told it three weeks ago and used that context to shape suggestions now. It didn’t overwhelm me with options; it helped me narrow them down.

And when I asked questions, it didn’t just answer. It asked better questions back.

By the time we landed in Kona, I wasn’t second-guessing anything.

I wasn’t wondering if we should’ve stayed somewhere else or structured the trip differently or skipped an activity. I wasn’t lying awake at 2 a.m. googling “is the Fairmont Orchid worth it” for the fifteenth time.

I felt confident. Ready. Excited.

We had a plan that made sense. And for the first time in years, planning a big trip didn’t feel like drowning in information.

It felt like thinking clearly about what we actually wanted—and then going out and doing it.

Next: Part 3 – Where Expectations Get Quietly Exceeded

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