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Hi, and welcome back to Try AI for Growth, the podcast where I share small, surprising stories of how I’ve used AI to make everyday life just a little easier. I’m your host, Sara Vicente Barreto, and today’s experiment is a fun one and especially relevant as many are packing bags to go somewhere.
For half-term this year, we were heading to the Island of Sal, in Cape Verde, for a sunny break. Two adults, two kids, and one mum — me — who needs to make sure there are 3 (ish) well-packed suitcases but has historically just done it on the go. Despite being a frequent traveller, I must admit it still takes some mental load to ensure we have all the basic needs, extras and potential alternatives covered. I knew we’d be spending most of our time at the resort, mostly relaxing, splashing by the pool, and doing a few activities. But with 24 hours to go and way more work than possible to fit in those 24 hours, I chose to procrastinate on work and packing and actually pre-empt this whirlwind more long-term instead.
I wanted to quickly answer a few questions that swirled in my head:
What do we pack? What are the needs for the different activities? What are the specific things to each person? (fluff toys or books included). And then the more specific to our destination naturally. What’s the weather really like in late October? What sports can we do? What can the kids do at the hotel? Are there places to visit? And do I need to book anything in advance?
So, in classic Try-AI-for-Growth fashion, I opened ChatGPT and decided to treat this holiday prep as an experiment.
And honestly, it turned out to be the most organised last-minute packing I had in a long time. At least I was not standing around at 1 am thinking – What else am I forgetting?
The Packing Experiment – Getting Started
For years, we had been saying we should just have a packing list for some of our most typical holidays. The more usual ones are skiing or resort destinations. We would be somewhere on our holidays and say, “Next time we really cannot forget this!” But every time we came back, it was not very different. Life took over and the packing list never got done.
I was driving at this point, so I used ChatGPT in conversational mode.
“I’m travelling tomorrow, and I haven’t packed yet. Can you help me prepare a packing list, knowing that I’m going to Cape Verde, the island of Sal. I’m going with my husband and my two children, age 12 and 8, she’s a girl, he’s a boy, and we will mostly be staying at the hotel. Can you tell me a packing list, please?”
The first list was good, it had a mix of things for everyone – like swimwear and sunscreen – things for the kids – like rash shirts and beach games and extras – such as a light sweater for the evenings or a small first aid kit. Clearly, it had already checked the weather forecast for the evening temperature.
Packing 2.0 – Enhancing the List
From here, I started refining and asked for categories – entertainment, sports activities and plane bag. At this point, I also provided my hotel name.
As I was driving and wanted to be able to use this list in printable format, I wrapped up our first conversation, asking for a table format by category. I feel some information was lost when I asked for the format, so it would have been better if I had defined this to start with. But I did not give up and added some of the simple things that are sometimes so obvious that we forget – like pyjamas or underwear.
By the time we were done “chatting”, I had what turned out to be a 2-pager by categories, and when I exported it to Excel added a column for each of us. Then, that night, all I had to do was “tick”. Oh, I love a good to-do list. And it was so much less stressful to just follow a list and feel more in control than doing some guesswork late in the night. This one is a keeper.
The real win?
I won’t have to do it again this time. And it is easily adaptable to other types of holidays. My husband was incredibly proud of me, too, and a bit jealous.
The next stage: get to know your destination
This one seems obvious, and I have certainly discussed how to use AI to enhance holiday experiences. But I will share it anyway, as there were 2 parts I wanted to cover – the hotel and the island. And until 24 hours before, I had not even registered the hotel we were going to. Yes, booking holidays is the one thing I don’t have to worry about in the household. Or at least not worry about as much.
Feeling like my packing would be under control, and still stuck in traffic, I moved my conversation forward:
What’s actually available at the resort? What do I need to book in advance?
ChatGPT provided me with a description of the hotel activities, specifying the ones that were included and which ones might be worth booking. I also enquired about the kids club and the water park, which I had no idea the hotel possessed until then. (I admit I went to take a look at the website when I got home just to be sure ChatGPT was not hallucinating!)
I felt like this time, I actually had a clue about what I was going to face when getting to the hotel. Usually, I reserve the surprise element, but with the family and large hotels, that is sometimes bound to cause some disappointment.
What about adventures
When we go to beach resorts, we rarely leave the hotel. However, I felt like Cape Verde was a destination I wanted to know a bit more about, and so next, I went into travel guide mode for ChatGPT:
“We are more into staying at the hotel than going out, but if I do choose to go out on a day trip once or twice, what would be kind of the top five highlights that you would recommend?”
Rather than a generic list, I got a list with explanations that would fit our family:
- The salt mines, which became one of the highlights of my husband’s trip, as anyone can float there
- Shark Bay for safe shark encounters, which was the lowlight of my trip, as I had to stand in the water taking photos of my delighted kids with sharks swimming between our legs. Ok, they were baby sharks, but some were going on toddlers!
- The Blue Eye at Buracona, a beautiful spot that merited a visit despite the long tourist queues.
- A walk into Santa Maria, the local town close to us
When we were deciding on the excursions to take, this information proved valuable to our planning (and negotiating). It was like having a personal travel researcher — without scrolling aimlessly for hours.
Accounting for everyone
The husband is a kite surfer, or at least used to be, so I also wanted to enquire how difficult this would be. With some AI help, I found out more about the weather, wind and waves, as well as the best beaches for kitesurfing. Not surprisingly, the spot is called Kite Beach. Duh.
The Overall Outcome: Holiday Mood
Sometimes, I get on the plane in a state of overwhelm. Not only do I have the feeling that I have probably missed some stuff in my late-night packing, but I also feel like I am not even aware of where we are going and what to do. It is not unusual to find myself googling as I am queuing to board the plane. With the ability to chat in a conversational format at a time that suited me (e.g. I did not have to be seated and typing on the computer) and the structured way in which I got the answers, I felt inevitably more in control and more ready to enjoy my holidays.
What to take away?
Pun intended naturally. Here are a few learnings from my experiment:
- AI can help you get structure – I had a bunch of ideas already of what I usually take, and through the conversational mode, I could have ChatGPT organise them for me in categories and complete as needed. AI on the go was definitely part of why it worked so well for me this time.
- Give good context – I explained the members of the family, the type of holiday and destination to ensure I got a packing list that made sense for everyone
- Define your format – I did not do great on this one, so I had to go back and ensure completeness when I copied my list into Excel. Had I asked for a table format with categories from the get-go, information would not have been lost along the way
- Check your answers – the waterpark seems like a hallucination, so I checked it when I got home. And guess what, it was true!
Wrap-up and happy holidays
This experiment reminded me that AI doesn’t replace the fun of planning a holiday — it removes the friction. It frees your brain so you can enjoy the anticipation instead of drowning in lists.
If you’re planning a trip soon this holiday season, try it. Ask AI to create your packing lists, check activities, or summarise weather trends. For me, it was key to remove the mental load.
Thanks for joining me on this episode of Try AI for Growth. If you’ve used AI for travel — whether it’s trip-planning or packing help — I’d love to hear your stories. Don’t forget to subscribe and leave a review.
Until next time, keep experimenting and keep having fun.