Introduction
Forget coding or deepfakes: Can AI actually plan a good vacation? I let ChatGPT (help) plan a week in Iceland, and you’ll no doubt be surprised at the results. Did we leave with more regret than memories? Or did Iceland (and AI) deliver more than we’d hoped for? Read on to find out!
To start, I gave it some loose thoughts based on what I’d heard about the island:
“Let’s plan a trip for Iceland! Thinking 5 days around Labor Day. Thoughts? It’ll be an outdoors focused trip. I’ve been told to do Hallgrímskirkja, Seljalandsfoss, Gullfoss, Skógafoss, Vík, Dryhólaey, Sólheimasandur, Icelandic horses, Jökulsárlón, Höfn, and Westman Islands. Not tied to these suggestions, a friend just told them to me.”
And ChatGPT delivered what looked to be a fairly reasonable plan. For example:
Day 2: Golden Circle Highlights + South Coast Start
- Thingvellir National Park (tectonic plates!)
- Gullfoss Waterfall
- (Optional: Geysir area if you want)
- Seljalandsfoss and Gljúfrabúi waterfalls (you can walk behind Seljalandsfoss — wear a rain jacket!)
- Sleep: near Skógar/Vík
Admittedly, I had used AI to help plan a trip before, so I knew a few things beforehand:
- You Know You: Tell AI what you like to do. Otherwise, you spend hours enhancing a bad plan.
- Convene a Panel: My favorite AI hack: ask your AI assistant to convene a panel of experts to comb through your plan; for Iceland, I used a local, a foodie, and a travel professional.
- Take Your Time: AI itineraries are not one prompt and done. They require refining, especially for logistics (ChatGPT loves to suggest action packed days, then Gemini tells you they are terrible ideas because it’s not possible to hike for 9 hours, drive for 16 hours and see sights for 3 hours).
So did ChatGPT’s itinerary work out? Was it even feasible? Let’s find out!
Day 0: Arrival
ChatGPT said:
“Arrive late in Reykjavík and grab the city’s famous hot dogs before crashing for the night.”
Reality check:
Our flight landed around 9:00 PM, so this was a fairly straightforward day. After grabbing the rental car, we made a quick pit stop at Bæjarins Beztu Pylsur in Fitjar for the late night hot dog; it wasn’t my favorite dog preparation, but worth trying once. We were still hungry, so we split a Sweet & Spicy pizza from Domino’s (cream cheese, dates, fresh chili, pepperoni, red onion) which was delish before crashing at an Airbnb just south of Reykjavik.
Verdict:
✅ Good plan
❌ Underestimated how hungry we’d be after a day of travel
Day 1: Reykjavik and the Golden Circle
ChatGPT said:
“Explore Reykjavík in the morning, then hit the Golden Circle: waterfalls, geysers, tomato farms, and ice cream before settling into Hvolsvöllur.”
Specifically, ChatGPT suggested the following specific itinerary:
Morning: Hallgrímskirkja tower, stroll downtown.
Afternoon: Brúarfoss hike (~1 hr), Friðheimar lunch, Kerið Crater, Efstidalur II ice cream, drive to Hvolsvöllur (~1h45).
Dinner: Midgard/MAGMA/Eldstó.
Overnight: Hvolsvöllur.
Reality check:
When we noticed that post-tropical Erin was set to bring gale-force winds to the island on a few of our key outdoor days, we consolidated our time in Reykjavik to just day 1, leaving our last full day for any weather makeups. That meant pulling Sky Lagoon into the early morning and seeing what we could pack in afterwards.
After a relaxing and rejuvenating soak–perfect after a travel day–we jumped right into activity mode: Hallgrímskirkja (it’s always worth seeing a city from above!) and very quick downtown stroll with lunch at Turf House–a whirlwind of a few hours in Reykjavik.
We hit the road and were able to tackle Brúarfoss faster than expected, leaving ample room to visit Efstidalur II (good ice cream), Strokkur Geyser and the surrounding area, including a quick hike for a bird’s eye view of the geothermal activity. We pivoted to Vínstofa Friðheima for dinner–Friðheimar’s sister spot which is open for dinner–and stopped at the massive Gullfoss Falls on the way. Despite the throngs of tourists, this literal hole in the earth is a must stop. Vínstofa did not disappoint; the beautiful greenhouse setting matched the incredible tomato soup.
We ended the night with the long drive to Hvolsvöllur, arriving around 9:30 PM.
Verdict:
✅ Hallgrímskirkja and Reykjavík are well worth the time.
❌ ChatGPT missed on not including Strokkur and Gullfoss (major oversights).
💡 It couldn’t predict the storm, but the Sky Lagoon pivot ended up being a clutch move that shaped the rest of the trip.
Day 2: South Coast Waterfalls
ChatGPT said:
“Chase waterfalls and black sand beaches along Iceland’s south coast before a cozy dinner in Vík.”
Specifically, ChatGPT suggested the following specific itinerary:
Morning: Seljalandsfoss, Skógafoss, lunch at Mia’s Country Van.
Afternoon: Dyrhólaey Arch, Reynisfjara Beach. Dinner: Smiðjan Brugghús or Soup Company. Return to Hvolsvöllur (~45 min).
Overnight: Hvolsvöllur.
Reality check:
Our Airbnb hosts recommended a quick hike at nearby at Gluggafoss, which we had nearly to ourselves. It did not disappoint: pristine water, serene surroundings, and no crowds. It was one of those off the beaten track kind of places that only a local can recommend. Seljalandsfoss and Skógafoss were equally impressive as they were crowded. Walking behind Seljalandsfoss was uber-cool, but Skógafoss felt skippable. Mia’s affirmed that I don’t like fish and chips; the quality seemed fine, just wasn’t my cup of tea.
With the weather still cooperating, we decided to tackle a longer hike. The Skalakot Manor to Waterfall came highly rated on AllTrails, and ended up earning a spot in our Best of Iceland Awards. The sheep on the trail far outnumbered us, and we ventured through rolling hills, a glacial gorge and a methodical climb to reach two waterfalls cascading from a crystal-clear sky.
By the time we arrived in Vik, the weather had turned–gusts of 60 mph and near-blinding rain. We braved it anyway to catch a glimpse Dyrhólaey Arch and Reynisfjara Beach, both impressive but not as awe-inspiring as our other stops (and we paid for this view, not only in money but in soaked clothing). Dinner at The Soup Company was a nice way to end the cold, blustery and rainy day.
Verdict:
✅ Seljalandsfoss is unique and The Soup Company was a great value!
❌ ChatGPT isn’t a local; it erred on the side of can’t miss “attractions” and left stops like Gluggafoss and the Skalakot hike out.
💡 Last-minute pivots to take advantage of good weather are critical! Have a plan B and C in your back pocket.
Day 3: Eastern South Coast, Glacier Lagoons, Höfn
ChatGPT said:
“Drive east through mossy canyons and glacier lagoons before reaching the fishing town of Höfn for dinner.”
Specifically, ChatGPT suggested the following specific itinerary:
Morning: Drive east, Fjaðrárgljúfur (~1 hr).
Lunch: Fancy Sheep Café.
Afternoon: Fjallsárlón, Jökulsárlón, Diamond Beach, Dinner in Höfn (Pakkhús/Humarhöfnin/Hafnarbúðin).
Overnight: Höfn.
Reality check:
After a long day 2, we slept in a bit, cleaned the Airbnb and drove east to Vík once more. Logistically, grabbing an early lunch made more sense than waiting for a very late one, so we grabbed bacon wrapped dates and a pepperoni, cream cheese and date pesto pizza at Black Crust Pizza. The food was equally as fun as sitting next to a group from the same town we went to college in–the world is indeed small.
As we left lunch, we decided to add a stop at Svartifoss after Fjaðrárgljúfur to get another hike in given the nice weather.
Both hikes were absolutely worth it.
• Fjaðrárgljúfur—a mossy green-and-brown canyon—looked exactly like something you’d find by Googling “cool Iceland sight.”
• Svartifoss, inside Vatnajökull National Park, offered a crash course in Icelandic geology. The grey-black hexagonal basalt columns framing the falls inspired the design of Hallgrímskirkja, the church we visited in Reykjavík.
With evening approaching, we skipped the glacial lagoons (Fjallsárlón and Jökulsárlón) and Diamond Beach and instead headed directly to Höfn. Along the Ring Road, we spotted a small parking lot, a glacier and a huge rainbow. A quick half-mile hike led us to Svínafellsjökull, where we were treated to unbelievable (and windy) views of the glacial tongue and surrounding mountains. This stop felt quintesentially Icelandic: beauty at every turn, especially the unexpected ones.
Dinner at Hafnarbúðin–drive thru chicken wraps, tenders and Nutella milkshakes–capped off an incredible day (this meal was seriously good–cashews, sesame seeds, cranberries and bell pepper elevated the wrap into the stratosphere).
Verdict:
✅ Fjaðrárgljúfur was great bang for the buck, Hafnarbúðin…*chef’s kiss*.
❌ Too much seeing and not enough doing; Fjallsárlón, Jökulsárlón, Diamond Beach are pretty, but unless you’re on a tour, they’re quick stops.
💡 Take that random side road. You never know what you’ll find!
Day 4: Hiking Near Höfn
ChatGPT said:
“Attempt the Múlagljúfur Canyon hike—if the fog allows. Otherwise, explore smaller falls and enjoy fresh seafood in Höfn.”
Specifically, ChatGPT suggested the following specific itinerary:
Morning: Múlagljúfur Canyon (~2 hrs).
Lunch: Café Vatnajökull.
Afternoon: Skaftafell – Svartifoss (~1.5 hrs).
Dinner in Höfn.
Overnight: Höfn.
Reality check:
We woke up to a dreary day in Höfn: low clouds, fog rolling in and choppy waters. In other words, not what you want to see when you’ve got the most important hike of the trip on tap. One thing working in our favor? We had already tackled Skaftafell and Svartifoss (on ChatGPT’s itinerary for day 4) and soaked in Sky Lagoon, giving us some wiggle room if the weather didn’t cooperate on day 4.
We picked up an early lunch from Fancy Sheep Cafe (on ChatGPT’s itinerary for day 3–Café Vatnajökull geographically didn’t make sense on day 4) on the way to the Canyon, where the weather was far worse than in Höfn. The air had turned downright frigid, with an icy breeze blowing off of Diamond Beach. Fancy Sheep’s pumpkin soup did its best to warm our souls, but we were left with little more than a tepid hope that we’d be able to hike.
At the Múlagljúfur trailhead, visibility fell to less than a quarter mile, and we called off the hike about a mile in. We drove east of Höfn and explored Skútafoss, which was pretty but paled in comparison to the grandeur of the other falls we’d seen.
We headed back to Höfn, strolled around town and enjoyed a second straight night of chicken tenders and Nutella milkshakes. Tenders are always there to pick you up.
Verdict:
✅ A Reasonable itinerary overall; all stops were (eventually) well worth it!
❌ ChatGPT struggled to find an alternative plan once the fog set in.
💡 Some days, you don’t win, and that’s okay!
Day 5: Return to Reykjavík & Sky Lagoon
ChatGPT said:
“Wind your way back west, stopping for one last glacier hike before soaking in Sky Lagoon’s geothermal pools.”
Specifically, ChatGPT suggested the following specific itinerary:
Morning: Depart Höfn ~08:00.
Mid-Morning: revisit Fjaðrárgljúfur (optional).
Lunch: Kirkjubæjarklaustur. Long scenic drive.
Evening: Sky Lagoon + Reykjavík Kitchen or Icelandic Street Food.
Overnight: Reykjavík.
Reality check:
By day 5, we were more off schedule than an offense facing second and 20. But that worked in our favor: we’d already visited Sky Lagoon, so we had the day to take another shot at the crown jewel: Múlagljúfur Canyon. And I was stressed; I had hyped the hike up so much that the success of our trip felt binary: do the hike, and the trip was worth it. Admittedly, this is a terrible way to think, but I am who I am.
On the way to the hike, we made one delightfully random stop: a Boeing 757 winglet on the side of the Ring Road paying homage to aviation mechanics. As Jon Ostrower says, “there’s always an aviation angle.”
Then, it was back to the familiar gravel road to Múlagljúfur. For the quality of hike, the canyon is still somewhat of a hidden gem; it’s far less busy than nearby Diamond Beach and Fjaðrárgljúfur.
The hike itself was spectacular (and if it were in the US, it would have easily made my top 10 US day hikes list); we traversed up, then down, then crossed a small river, then headed back up to the rim of the canyon, where biblical sized mossy walls reveal two hidden waterfalls pouring water into a hole in the earth larger than you’ve ever seen. The views felt endless, though they were quickly obscured by fog that rolled in nearly as fast as it rolled out. An epic way to conclude our time out east, and we were plenty satisfied as we rolled back to Keflavík.
Lunch at Café Vatnajökull (which ChatGPT suggested for day 4) delivered, giving us plenty of fuel for the six hour drive west. We zoomed past green hills, grey peaks, blue lagoons, and white glaciers. We traversed through miles of flat, black land. We navigated mountain passes. And then…Reykjavík! We grabbed take out at a Thai spot before settling into our Airbnb in Keflavík.
Verdict:
✅ Múlagljúfur Canyon was the highlight of the trip.
❌ Repeating Fjaðrárgljúfur felt unnecessary, especially on a short trip.
💡 Stay in Keflavík before an early morning flight! We were door to rental car drop-off in 10 minutes.
Final Thoughts
This was the second big trip I planned with ChatGPT, and both left me with the same conclusion: AI’s helpful in spitting out a rough draft in no time, but it does not replace local knowledge or your own travel style, no matter how many times you tell it. If you’re thinking about planning a trip with AI, keep these three lessons in mind:
1. AI will get confused and lose parts of your itinerary. Keep track of what you tell it! Restaurants or activities can mysteriously vanish, only to appear 30 messages later. The good news? Prompting the AI directly usually brings dropped items back.
2. Convene a “panel”. Ask ChatGPT to convene a panel of experts who reflect what you care about. For us, it was an adventurer, a foodie and a travel expert. They’ll force the AI to refine its plan in a way a single “voice” can’t.
3. AI does not replace other resources. Read blogs, post in Reddit, text friends who’ve been to your destination–AI cannot replace firsthand accounts!
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