ChatGPT Transformed My Vacation Planning Process

Before I embark on any trip, my primary goal is simple yet daunting: to learn everything I possibly can about my destination. It’s a time-consuming process, but for me, it's always been a necessary one.

That is, until I discovered a new use for ChatGPT while planning a trip to Door County, Wisconsin. Instead of dedicating hours to my usual background reading, I let OpenAI's chatbot handle the heavy lifting. While I travel frequently and have experimented with various AI-powered trip planning tools, this was the first time an AI application genuinely made my process more efficient.

Previously, using ChatGPT for specific recommendations like restaurants or attractions yielded generic results that didn't align with my personal tastes. But for replacing the exhaustive pre-planning research? It was a game-changer.

My Traditional, Time-Consuming Research Method

My usual process is intense. Once a destination is chosen, I dive into a sea of Google searches with queries like "Top attractions," "must-do activities," and "neighborhood guides." I open more browser tabs than one can count and read through the top results for each search.

Then, I dig deeper with more niche searches, scouring Reddit threads where locals discuss their own neighborhoods. The final step involves scrolling through platforms like TikTok to get a visual feel for the place and, crucially, to identify which viral spots I should probably avoid. It's an excessive routine that takes hours, but it leaves me feeling incredibly informed, confident that I can make the best choices for my trip.

Letting AI Handle the Heavy Lifting

For my recent trip to Door County—a beautiful peninsula in Wisconsin known for its natural scenery—I knew I needed to act fast to book a house on a busy weekend. So, I decided to try something different and turned to AI.

I tasked ChatGPT with providing the kind of comprehensive overview that usually takes me hours to compile. I used a series of prompts, asking it to summarize popular attractions, identify which ones are often called overrated, and provide tips on the best times to visit. I also requested varied sample itineraries to get a full picture of my options.

I even described my travel preferences—a love for good food, nature, vintage shops, and local haunts away from crowds—and asked for recommendations on which town to stay in. The chatbot quickly provided a summary of what each town was known for and which would best suit my style.

The Results A Powerful but Imperfect Assistant

In about thirty minutes, I felt I had a solid understanding of visiting Door County. The AI was able to synthesize the common recommendations that appear on countless lists while also highlighting more unique options. I asked follow-up questions to challenge its overly optimistic or marketing-heavy responses.

However, the results weren't perfect. ChatGPT recommended at least two restaurants that had been closed for years. So, while I may not have known the destination as intimately as I would have through my own manual research, I knew enough to feel confident in my decisions. I booked a rental home that same night, a move that would typically have taken me much longer.

While AI has streamlined my initial research, old habits die hard. I'll still do some of my own reading to uncover those truly hidden gems. But for saving hours on foundational planning, ChatGPT has earned a permanent spot in my travel toolkit.