The trip starts when you start planning it. For me, planning is integral to the travel experience. I enjoy the planning. So, no, I don't and won't use AI for travel planning.
However, this is a thought exercise, so I passed it on to Gemini.
Here is it's response:
Gemini said
The WSJ experiment by Dawn Gilbertson is a perfect case study for the current state of travel technology: AI is an excellent visionary but a terrible travel agent. While the narrative of "muddling through" makes for a charming travelogue, it exposes the fundamental friction between algorithmic logic and the messy reality of the physical world.
The Illusion of Competence
The central tension in letting Gemini (or any LLM) plan a trip is the "Last Mile" Problem. An AI can scan millions of data points to identify Saltburn-by-the-Sea as a picturesque destination, but it lacks "situational awareness."
A critical eye must note that while AI is great at generating text, it struggles with spatial relationships. For instance, Saltburn-by-the-Sea is famously located in North Yorkshire, not Northumberland.
While these two regions share a stunning coastline and a cold North Sea breeze, an AI conflating them can lead a traveler to the wrong county entirely if they aren't careful. This "geographic blurring" is a hallmark of AI travel planning—it understands the vibe of a region but often fails at the specific boundaries.
The Dryrobe: A Bridge to Reality
The mention of the Dryrobe in the article is perhaps the most grounded takeaway. It highlights the gap between "planning" and "experiencing." An AI can tell you to go for a swim in the North Sea in April, but it doesn't "feel" the bone-chilling 7°C water.
From Devon to the Great Lakes: Transitioning a Dryrobe from the English coast to Lake Superior is a savvy move.
The Utility: In the North Sea or the frigid depths of Superior, the "winter dip" isn't just a hobby; it's a battle against hypothermia. The Dryrobe represents the kind of specialized, local knowledge (the "what to bring") that AI often misses in favor of "what to see."
The Verdict: Would You Let AI Plan Your Trip?
If you view a trip as an adventure in troubleshooting, then yes—let the AI take the wheel. The errors become the "inciting incidents" of your story.
However, if your goal is relaxation or efficiency, AI should remain a research assistant. It is best used to generate a "long list" of possibilities which you then curate using human intuition. The WSJ reporter succeeded not because of the AI, but because of her own ability to pivot when the AI's map didn't match the terrain.
Ultimately, AI can point you toward the water, but it's still up to you to know which coat will keep you from freezing when you get out.
Do you think the risk of a "hallucinated" itinerary adds to the adventure, or is it just an unnecessary headache for a short break?