I Used ChatGPT to Plan Trip to Door County, Wisconsin. It Saved Me Hours

Before I plan a trip, I have a straightforward goal: Learn everything there is to know about the place I’m visiting.

I know, I know. That sounds time-consuming. And truthfully, for me it is.

But for ChatGPT?

I stumbled upon this AI use case when starting to plan a relatively uncomplicated trip to Door County, Wisconsin, for later this summer. Rather than doing the hours of background reading that I usually do to get the lay of the land in a new destination, I let OpenAI’s chatbot do it for me.

For context, I travel frequently in my personal life and cover travel for Business Insider, but until now, I’d yet to find a use case for AI that I felt really made my trip planning process more efficient.

I’d experimented with AI-powered trip planning tools but had never found them particularly useful. I’d also tried using ChatGPT as a glorified Google, describing to it vaguely what my interests were and asking it to recommend restaurants or attractions. The results were less than promising. From what I could tell, our individual tastes are still too personalized — and chatbot answers too universal — for specific recommendations to be helpful.

But for replacing all my pre-planning background reading? It was great.

AI does all my background reading for me

Let me give you a sense of my usual process.

Once I know I am visiting a place, I will Google the most generic things a tourist could think to ask: Top attractions. Must-do activities. Neighborhood guide. Best restaurants. One-day itinerary. Three-day itinerary. Weeklong itinerary.

I will do all of these searches, open more tabs than any browser should be reasonably expected to host, and then, I read.

I read the top 10 or so results for every search. Then I do more niche searches like best neighborhoods to live in or best vintage shopping, and do the process all over again, this time also rifling through countless Reddit threads where locals discuss the goings-on in their own neighborhoods.

Next, I move to social media — often TikTok — to scroll all the videos I can find about the destination to get some visual context and, most importantly, to learn which restaurants or attractions are viral so that I can avoid them.

It takes hours, and it’s arguably more information than a tourist technically ever needs. But by the time I am done, I feel I have a shockingly full understanding of a place, as both a tourist destination and even as a place where real people live. I feel I could recommend to my friends which neighborhood would be uniquely right for them, which highly-rated restaurants are overrated, and which niche museum is actually a lot cooler than the one ranked first on TripAdvisor.

The process is excessive, but it gives me confidence that when I get to the hard planning stage — selecting a neighborhood, narrowing down hotels or Airbnbs, booking restaurant reservations — that my hard-earned PTO is being put to its best possible use.

Luckily for me, it turns out ChatGPT is pretty good at doing this.

ChatGPT helped me plan my trip to Door County, Wisconsin

I was recently planning a trip to Door County, which is a small peninsula in northeast Wisconsin situated between Lake Michigan and Green Bay that’s known for being one of the prettier natural places in this part of the Midwest. I wanted to book a house on the water for a busy travel weekend, so I knew I needed to do it quickly.

So, instead of embarking on my usual trip planning odyssey, I did something that I had previously been very skeptical about: I turned to AI.

The kind of comprehensive overview that I get from reading all the top Google results, ChatGPT was able to give me with just a few prompts. I asked which popular attractions are frequently called overrated and which ones people say are worth weathering the crowds. I asked it to include any tips or tricks on the best times to visit certain places, and to provide several sample itineraries that were varied so I could get a complete picture of my options.

I even described my vague travel preferences — good food, good drinks, nature, away from crowds, vintage shops, where locals actually go — and asked it what town I should stay in. It gave me a quick summary of what each of the towns were best known for and which were most likely up my alley.

I also asked follow-up questions and played devil’s advocate, as AI can tend to repeat marketing-speak or be overly optimistic.

In about half an hour I felt like I understood visiting Door County almost as much as I would’ve if I had spent those hours consuming everything myself. It’s able to summarize the 90% of recommendations that pop up on every list and then also include the more unique ones.

The responses were not perfect. It recommended at least two restaurants that closed several years ago. And to be clear, I doubt that I know Door County as well as I would if I had done all that reading myself.

But I felt like I knew it enough to be confident in my choices while planning — enough so to book a rental home that same night, a decision that would generally take me a lot more time.

And yeah, I’m still going to do a bit of excessive reading for the hidden gems. What can I say? Old habits die hard.

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