Spring Break taught me a lesson about procrastination this year. I wrote about this in a previous post – Netflix Has a Personal Plan for You. Do You Have One for Yourself?
When your days are packed full of responsibilities, it’s easy to put off planning your next vacation, but after the Spring Break debacle, I was determined to plan a kick-ass summer vacation for the fam this year.
There’s just one problem. When you can go anywhere in the world, how do you decide where your next adventure will be?
Choose Your Destination
Luckily, we all have a personal travel agent right at our fingertips. Mine? It’s ChatGPT. Determined to avoid the rabbit hole of endless internet searches and decision fatigue, I turned to my trusty AI sidekick.
Instead of starting with the destination, flip the script. Focus on what you want out of the trip. For me, it was relaxation, adventure, and family fun. This is where the magic of a well-crafted prompt comes into play.
Here’s the prompt I used:

ChatGPT responded with a list of tailored suggestions:

Suddenly, the fog lifted. Nassau and Cancun sounded fabulous but a bit much for our laid-back vibe this year. Florida, on the other hand, seemed perfect, but not Miami. Too much hustle and bustle this time.


I visit Fort Lauderdale for work frequently, so that was out. But St. Petersburg/Clearwater? Now, that had potential.
A quick click to the recommended hotel website and I was sold in seconds.
The intro video captures a stunning fly-over of the picturesque resort, showcasing waves gently lapping the shore and vacationers basking in the sun. Families engage in various activities, with children soaring along ziplines, zooming down inflatable waterslides, and playing on the expansive inflatable waterpark in the ocean.
It was exactly what we wanted. I could almost hear the kids’ laughter and feel the sun on my face.
Compare and Select Options
Now, onto the fun details.
With ChatGPT (or another AI), you can dive into the nitty-gritty:
Compare room options: Put the link to the accommodations page into the chat and ask for a room option comparison. Is $35/day worth extra space for the kids to spread out and avoid fighting because we are all crammed together? Yes, please!
Create your bucket list: Find a link that describes “what to do” at your resort or in the area you’re visiting. Enter the link into the chat and talk with your AI travel agent to identify your must-do items for your trip.
For example, our resort’s “calendar of fun” is displayed beautifully but isn’t functional. You’d need to click on every single activity to see what days it’s offered, find a working pen, write it down, and organize it all.
No, thank you. That’s a lot of work for a vacation!

Instead, take the link to the page, drop it into your AI chat, and ask for help.

In our case, I followed up and asked AI to format the list into items available every day and a list by day of things only available on certain days. Voila! Organized and easy!
Once you have your list, it’s time to get it out of AI and into your hands. You could copy and paste it all, but why not make it simpler?
Ask your AI travel agent to export the list into a Word or Google Doc, and you’ll be ready to access it from your phone or print it and take it with you.
The delicious details: Now, let’s talk about the best part of vacation: the food and drinks! Use your AI travel agent to decide where to indulge. Our resort boasts 12 restaurants, but I didn’t want to spend time researching each one. Instead, I shared the link to the “eat and drink” section of the website and let my AI guide me.

Perfect! Palm Court Italian Grill and RumFish Grill emerge as the top must-tries. While AI can’t make your reservation on OpenTable YET, it undoubtedly will soon.
Finding hidden gems: The last task is to find what you’re missing. For example, I remembered seeing an offer for a free beach photo shoot but couldn’t recall where.
I simply pasted the website and asked for help. In less than a second, I had my answer.

AI: Beyond the Office and Into Your Life
Generative AI in the workplace receives a lot of attention, overshadowing the life-changing, time-saving expert it can be for your personal life.
This is just one example.
I’m using AI daily to simplify my life and free up my time to do the things I love. Booking this entire vacation took me less than 90 minutes!
I’ll continue sharing examples here, so stay tuned.
I can’t wait to make a custom GPT with our dietary preferences and use it to find new restaurants. Goodbye to going to the same restaurant for the 857th time
If you’re brand new to AI and have questions, ask me through the contact form on the website or DM me on social media (LinkedIn or Instagram). I’d be happy to help you get started on the path to a simplified life.

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