AI Is Planning Our Family Vacation [Raw Session]

00:00 — AI as an ongoing travel assistant

Hey, welcome back to Slow Builds. So, this is a funny one because we are taking another family vacation over Christmas this year and basically AI is completely planning the entire trip. Um, it's funny because it's doing everything. And I don't mean just ChatGPT to give me 10-day itinerary of Puerto Rico. Um, that's where we're going. Um, I've done that kind of thing before.

You tell it where you're going, what you like doing, and it gives you a bunch of suggestions, some ideas, places on a map. That's useful, but this has turned into something completely different from that. A whole new ball game that I'm coming across here now. Um, I've actually got a project set up in ChatGPT. I am using it specifically for this vacation.

It's on my phone. It's on the laptop. I can access it pretty much from anywhere, whenever I want. And over the last little while, it's become almost like it's my personal travel assistant. It's my travel agent. It's everything. Uh more or less, it's uh my concierge, I guess. But the thing I find interesting is that I'm not really sitting down and planning the vacation in the traditional sense like I've done before.

Um I'm just going about my day, finding things that interest me, throwing them into the project, and letting AI figure out what to do with them. And it's actually working surprisingly well. And the way I normally do vacations are find a place. Um, and that takes quite a bit. There's a lot of flight planning, a lot of uh where we're going to stay, what type of vacation it is, um, car rentals, how many people are going, who's going, where we are.

There's a lot of work involved, and it's very stressful to get it right. It's very stressful to make a vacation feel like it's spontaneous, uh, when it's definitely not spontaneous at all. Not from my point of view, but I enjoy it. I have very much fun.

02:03 — Price monitoring and changing our bookings

So, originally I was using AI to help with more traditional parts, booking a vacation, flights, Airbnb, rental car, that kind of stuff. I still made all the bookings myself. So, once I figured out where we're going to go, I went on and I booked our flights, made sure they're refundable, um just because I did it so early and I really wanted to experiment with this.

And same with the Airbnb and same with the car rental. And so all that was taken care of scheduled. And I started setting up scheduled tasks that would keep going back and checking things because normally when I book a vacation, I spend a bunch of time trying to get a decent deal. Then once it's booked, I don't really pay much attention to price anymore.

Once I feel comfortable in the past, I just went along with it. And I figured why not let AI keep watching? So now I've got task or my dot or whatever it is is checking prices and looking at different options. Some things happens daily, others are weekly depending on what I'm trying to monitor. And we've actually made changes because of this already.

We've switched our flights twice, changed Airbnbs, and managed to get discounts on our car rental. Now I still have to look at the options and decide what to do. It's not just making reservations or canceling things without me knowing about it, but it's taking away a lot of that ongoing research. And that's nice because I don't particularly want to spend every evening checking 20 different websites to see whether I can save another $100.

But the money-saving part is really only where it's kind of started here.

03:35 — Screenshots become a vacation scrapbook

This is probably my favorite part of the whole thing. I'll be sitting on the couch lying in bed scrolling through Instagram, Facebook, Reddit, whatever. Any place I find information popping up. I'm looking up stuff, events. I'm looking up um different spots, different food areas. I love ice cream, so I'm always looking that up. And somebody will post a video of a beach, a waterfall, a restaurant, or some little place in Puerto Rico, and I'll think that looks interesting.

Normally, I'd save the post, maybe take a screenshot, and then completely forget about it. I try to remember, but uh it gets complicated when you don't have the right tools. Or I'd have all these things saved scattered between all the different platforms, Google Maps, my camera roll, and then when we're actually on vacation, I don't remember half of them.

I'm trying to look it up. I think there's a place here or just around the corner, but I can't find it. But now I just take a screenshot, open ChatGPT on my phone and drop it into the vacation project. Sometimes I don't even explain anything. I never explain anything to be honest with you. I just give it the picture and that's it. And sometimes I forget about that, but I go back and get a nudge or get a reminder like, "Hey, that thing you posted." Um, and it'll try to figure out what the place is, where it's located, and whether it makes sense for our trip.

It checks the itinerary we've been building. Looks at what else we're doing and tells me whether the place is already included, which sometimes it is. Sometimes it comes back and says like it's already part of your process. Great, great job. Other times it'll say it's actually close to somewhere we're going on a particular day, so we could add it as a possible stop.

Or it suggests that something might be worth replacing with this new place. And sometimes it tells me it probably isn't worth the extra drive or it's not as good as the alternative we already have picked. And that's what I find extremely interesting about this. I'm not organizing all of these things into categories or trying to figure out which day they belong on.

I'm just throwing ideas out at the wall here. Here's a picture. Here's a link. Here's an ice cream shop I found. Here's a place somebody mentioned on Facebook. Is this worth going to? Where is it? Are we already doing this? It's almost like having this scrapbook of things that interests me, except the scrapbook is actually looking at everything and trying to organize it into a vacation.

And I don't have to remember all the little details myself.

06:13 — Learning what our family actually enjoys

Um, and as we're planning, I've been telling AI more and more about what we enjoy doing as a family. And snorkeling is a big part of us when we go on beach vacations. And we're not necessarily looking for organized excursions every time. We actually don't like them at all. Really, we love the idea of renting a car, finding a beach where we can get into the water ourselves and seeing what's out there.

Like, but sort of knowing where we're going and what to expect. Turtles, stingrays, fish, squid, whatever we might come across. Statues. We've been down places in Miami where the cars and stuff are underneath water. Uh, we like exploring different beaches, walking around towns, finding food trucks and interesting restaurants. And we really like ice cream.

If no one knows that, I love ice cream. Actually, just desserts in general, bakeries, cookies. I love a great coffee. Little shops where we can stop in and try something. So now when AI is putting together a day, it's not just looking at the major tourist attractions. And it knows that we don't really flock to that either. And it knows we're not the kind of people that love going into museums or looking at ruins and stuff.

We'll walk by it. It's part of a hiking day. It's part of the trip and the experience. And we want to experience it, but we don't make it the overall. And AI knows that now. So, it's finding these little places along the way. Maybe we're driving to a beach and there's an ice cream shop 10 minutes away or there's a little food truck area close where we're going to be around lunchtime.

And it'll add those as possible stops. Not necessarily things we have to do, but options. And that's important to me because I don't want to go on vacation, have every minute of every day completely scheduled. And I've talked about this before. You want down days. You want days where you can feel free to do what you want and not make the vacation become a job basically become a burden.

Um other times we'll get somewhere and decide it's not worth staying so we'll just leave. I just want to know what's available around us so we can make those decisions and this has given us a pretty good starting point.

08:06 — When AI questioned the mountain drive

Um there was something that happened recently that really stood out to me. I found this ice cream shop in Puerto Rico that's apparently been there for 80 years I think and they make all their own ice cream and it's like this is exactly the kind of place I want to go. It's up in the mountains. I had no idea where it was, what part of the island, how to get there, any information about it.

I just posted a picture and it told me it's up in the mountains and I thought it might be a neat place to visit once it told me that. So I gave ChatGPT the name and asked whether it's worth driving all the way up there. I don't know why AI put that in. I didn't ask it. I just posted the picture. It came back. It found it. It found the location.

It found where it was. It knew exactly all the information. And I didn't have that information. I had a picture. And what I expected was usual response about how interesting place was, what they're famous for, and why we should check it out. But that's not what really happened in this case. It looked at where the place was, the drive to get there, and what else we had planned around that area.

And then it brought up something about my wife. She doesn't particularly enjoy winding mountain roads with the Road to Hana on Maui. She vows never to do it again. You drive for miles and get nowhere and you're sick because there's so many turns. And AI remembered that I brought that up. It actually compared the drive to that same spot based on conversations I had about her other travels, images that [unclear] access to, videos we have access to, and basically told me that while the ice cream shop might be interesting, the drive could be uncomfortable for her.

And there wasn't necessarily enough else in that area to make it worthwhile. Um, there was a great coffee shop there, but I'm the only one who drinks it. So, it's not worth going 40 minutes out of the way in an uncomfortable drive for ice cream and then have to drive 40 minutes uncomfortably back again. So, maybe it wasn't the best use of our vacation days.

And I thought that was pretty interesting because it wasn't just recommending something based on ratings or popularity. It was considering whether we'd actually enjoy going there. And that's a different kind of usefulness. Of course, I still want to verify the road conditions and details before making the decision to remove it, because AI can be wrong on a lot of these things.

And maybe there are other things there that it doesn't know about. Maybe there's a Christmas event happening, uh, a Christmas parade or maybe there's something in the mountains or a special event that might make it worth the trip. But again, it gave me the details. But even having it raise that concern without me specifically asking about why about the winding roads was very useful.

It kind of— it's making decisions for me or at least helping me make the right decisions faster.

11:03 — A website and spreadsheet for the trip

Um another thing that's been happening is that the AI has started building out complete days for us. We have a— what it did is it built a full out website. So I'm using ChatGPT. So I think it's called sites. I'm not sure what it's called on there actually the dot made it and whatever. So I built this complete website for the trip and there's also a spreadsheet breakdown of itinerary timing driving distances and cost of everything.

So instead of just having a big list of things to do, I can look at a particular day and see how it might actually work. The whole website is interactive. It has all the days from the day we leave to the day we had to fly home and every day in between.

11:46 — Making the drive part of the vacation

And for example, there's one day where we have a fairly long drive plan. And AI is looking at what time we should leave, how long it should take us to get there, and what we might be able to do along the way. So we just don't just waste a full drive rather than just like driving for hours to get somewhere. It's trying to figure out what would match up with that day to make it break it up and make it more enjoyable for us rather than just it's finding things like there's a lighthouse along the way we can go to.

There's a cliff. Uh there's a Gilligan's Island, I think, and then there's like a pink lake that should be very interesting to see. Places we might otherwise drive right past without knowing they were there and just focus on getting to the destination. It's making the journey to get there more enjoyable for us without me asking it to do it.

And then I have another activity I wanted to do on the same day and basically it pushed back and suggested moving that somewhere else because it— it said you'll be too rushed. It's going to make it an uncomfortable day uh and a waste of your time. So we ended up building another day around that activity instead. And I like that. I don't need AI to agree with every idea I have.

I'd rather it tell me when something doesn't make sense. Especially when we're dealing with the limited number of days and we don't want to spend the whole vacation racing from one place to the next just to get it done. That's not a vacation. That's a chore. That's a duty. Like it's not fun.

13:14 — Discovering days already in our itinerary

Um like just last night I was asking about something we might want to do and ChatGPT told me it was already included in one of our planned days. So I asked what else was planned for that day and it went through the whole thing. It sent me a link to the website and it showed me it and listed everything and it showed me where we'd drive, places we'd stop, the different beaches, what we'd see along the way, and where we could stop to eat.

And I was reading I was going through the website, reading the notes, following along in the website, and I was like, "That sounds like one of the best days ever." I didn't even realize we put together a day quite like that. I had no idea how extensive this thing went with how it was building out the trip around what we wanted. And I say, but really a lot of it was AI pulling together all these different things I've been feeding into the project.

So I asked whether we had another day like that on the other side of the island. And it started explaining another day we'd already been working on. Part of that day was pretty much what I was looking for. And then it explained what else we could do in that area. And again, I was thinking that sounds amazing. It's a weird experience because I'm discovering parts of my own vacation that are already sitting there. These aren't necessarily places I would have thought to group together myself.

They're coming from all these different conversations, screenshot places I've saved and research that's been happening over time.

14:48 — Sharing the trip and keeping the context

And then there's the fact that I can just tell AI to build me a website for all of this so I can share it amongst our family, the people going on the trip so people from home can know where we possibly are at any moment and they can get excited for us or at least be a little bit uh feel comfort having an idea of where we may be. And I can see the trip laid out, look through different days, see the places we're thinking of visiting and review the cost too.

There's a spreadsheet for the more detailed breakdowns and the website for looking at the overall trip. It's amazing experience. I'm actually very impressed with it. It's not perfect and I'm still adjusting things, but it's becoming the central place where the planning lives and because it's a ChatGPT project, I can pick up where I left off whether I'm at a laptop, on my phone, anywhere, and I don't have to remember which conversation we had about a particular beach or which website I saved from some restaurant.

I can just ask about it again. As long as the information has been kept up to date in the project, it can use the context and help me figure out where things stand.

15:53 — Rethinking the travel app I wanted to build

And what's kind of funny about this is that I've actually thought about building a travel for many years. I thought about building a planning software like this. Um, as so whenever I run into some problem that I think could be solved with software, I start thinking about how I could build it. And travel planning is one of those things I've always thought about.

I've always liked the idea of having somewhere to collect information, everything about a trip. Not just the hotel and flights, but all the little things you discover along the way. A place somebody recommends, a restaurant you see online, some random beach that looks interesting, and then having something help organize all the information based on where you're going and what makes sense.

That sounds like a pretty substantial application to build really. Like that's why I kind of didn't do it. And now I'm doing a lot of it just by having conversations with AI, setting up some scheduled tasks and asking it to create the views and information I need. I'm not saying this is the same thing as having a fully developed reliable travel application.

There are definitely limitations and some of those details still need to be checked. But for my own use, it's doing much more than I expected and it's making me think differently about what I actually need to build because sometimes the thing I wanted from the software wasn't really the software itself. It was just being able to get something done without all the manual work, all the checking, all the time saving, all the comparing.

17:21 — We haven't taken the trip yet

Now, the funny thing is we haven't even gone on the trip yet. So, I really don't know how well all of this is going to work once we're in Puerto Rico. Some places might be closed. Some of these driving times might be too optimistic. I hope they're not. A beach that looks amazing in pictures might not be great when we get there. And I'm sure we're going to change our minds about things once we're actually on vacation.

And that's normal. And that's the way I like it. I like it to be free. I don't want to turn this trip into where we feel like we had to follow a full AI generated schedule. If we find a beach we love and want to spend another two hours there, we're going to do it. We're going to alter the trip no matter what. The idea is to have more information and better options, not to take away the freedom to explore.

And I still need to check important details myself. But even if half the itinerary changes once we get there, I think the planning process has already been worthwhile. It's given me multiple options, multiple, uh, different ideas. It's actually scheduling based off weather. Weather could change everything. The event could pop up or event could be cancelled.

Uh we've saved some money already. We found places I probably wouldn't have discovered on my own and put together what looks like a pretty interesting vacation, a fun vacation at that. And I've spent a lot of time trying to organize all these scattered ideas myself. And it's doing it for me.

18:42 — Help deciding what's worth our time

I think what I'm starting to realize is that this isn't really about AI planning the perfect vacation. It's more about having something that's continuously helping me think through the vacation. I can find something interesting and throw it into the project and keep going on with my day. And when I come back, I can have a conversation about how that idea might fit into everything else.

Sometimes it gets added, sometimes it gets moved, sometimes AI tells me we're already doing it or something close to it or that the idea is probably not worth something we wouldn't even like or not even worth looking at. And that's fine. I don't necessarily need more things added to the itinerary. I need help figuring out which things are worth our time.

That might be the biggest difference from how I've used AI in the past. I'm not just going to it for one answer and then moving on here. I'm letting it become part of the ongoing process where the information keeps building and the plans keep changing. And we'll see how all this turns out when we actually get there. Maybe I'll come back thinking this is the best way I've ever planned a vacation.

I hope so. Or maybe I'll come back with a list of all the things AI got wrong. Probably a bit of both. I guarantee there's going to be a lot of both. But right now, I'm enjoying the process. And honestly, I think the trip is shaping up to be pretty amazing. Actually, I'm very excited about it.

20:08 — Alternatives at each stop and a follow-up

Um I'm excited to take a lot of the stress off myself. I'm excited to have a lot of things mapped out and it's making me think now I need to say for each location major spot. So each stop along the map basically give me multiple of alternatives for each place. So if one place is closed or someone doesn't like this or we want to share and try multiple things.

So like a sandwich or a dessert or jump into that beach and walk on that hike. Like I want to have all these different options available to me at any time along the route basically. So I'm definitely going to do a video possibly when I'm there hopefully. I'm not going to go out of my way to do it, but I'm definitely going to do a follow-up video once we're done.

So hopefully in the new year that'll be one of my close to uh end of the year videos where I'm almost close to pushing it this to the one year mark. I think it's January 27th is when I started. So, the year is my mark and this vacation video is going to come close to the end of it. So, thanks for watching.