I Let ChatGPT Plan My Family Reunion Vacay

Here's how it went and what I'll do differently next time.

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Published December 12, 2025
Margeaux Walter

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Last year, my mother tasked me with organizing our first family reunion. We are 14 people ranging in age from 2 to 80, and we were coming from New York, New Jersey and Chicago. What could go wrong? I turned to ChatGPT with the following prompt:

We want to go on a family reunion vacation. No one should fly for more than 3 hours, and we all need direct flights. We want to stay at a beachfront resort that offers activities for all of us. We want it to be moderately priced, but don’t have a specific budget. The resort should be within a half hour of the airport.

AI suggested the Dunes Village Resort in Myrtle Beach: a short, direct flight for everyone, featuring an indoor waterpark, beach and a variety of resort activities, including basketball competitions and magic shows.

Here’s what we loved

The resort was absolutely perfect for a family reunion. The Dunes Village Resort was 20 minutes from the airport. Each family stayed in a suite that contained a full kitchen and accommodated six people. We were able to order a DoorDash dinner each night to my room, where we all had plenty of space to gather and eat. The beach and the indoor waterpark provided ample activities for everyone.

Here’s what I would have done differently.

The food aspect of this trip was quite challenging. I had assumed that we could eat at the resort or grab food at a nearby restaurant. However, ChatGPT never suggested that we rent cars (it specifically advised using Uber to the resort). Unfortunately, we had to take an Uber whenever we wanted to eat, as there was nothing within walking distance, and the resort offered limited food options. We ended up ordering all our dinners via DoorDash, Ubering to some lunch spots, and eating small breakfasts in the room. It added up very quickly. But next time, I would have been much more specific about our food needs. (I would have asked for a spot that had plenty of restaurants within easy walking distance, or I would have looked for a resort that had many restaurant options.)

Here’s what I suggest you ask ChatGPT when you’re planning your vacation.

Be specific about each requirement, including the length of the flight, the amount you want to spend, the weather you’d like to experience, the food options, and more. If you’d like to use my prompt (adjust as necessary for your own), I’ve written one for our next reunion, which we plan to hold next September.

We are planning a family reunion and have people flying in from New York, New Jersey and Chicago. Flights should be no longer than 3 hours, and we only want to fly direct. The resort should be within a 30-minute drive from the airport. We want to spend a maximum of $400 per night per family of four for the resort, but can bump this up to $600 per night if food is included. Flights should cost no more than $500 per person. We are ages 3 to 81. We would like to be within walking distance of the beach and numerous restaurants. There should be indoor activities in case of poor weather. We’d prefer a sunny destination, but can do a non-sunny, non-beach spot if it offers a ton of activities. This should be at least 4 stars, and reviews should be positive.

Before you book, remember this.

ChatGPT has a really bad habit of wanting to please. So, it might recommend spots that are not quite a good fit. Be sure to check reviews and verify that all your requirements are met. ChatGPT should only be your first step in vacation planning. It provides suggestions, and then you need to dig deeper, examining prices, location and amenities, because while AI may be extremely helpful, it has its limitations.

Pro tip

Before you go, download the Splitwise app. That way, anyone can grab the check for the meals and add the expenses in the app. Splitwise will divide the bill between the families, making it super easy to monitor expenses.

Have any of YOU ever used ChatGPT to plan a trip? How did it go? Let us know in the comments below.

Danielle Braff is a Chicago-based writer who knows how to find the heart (and humor) in everyday life. When she’s not reporting or crafting smart, relatable stories, she’s juggling life with her husband, two daughters, two cats, and one very lucky dog. A devoted traveler, lifelong reader, and unapologetic ice-cream enthusiast, Danielle brings curiosity, empathy, and joy to everything she writes. Discover more of her work at Daniellebraff.com.