Frequent Miler on the Air - How are you using AI for trip planning? | Question of the Week Ep7 | 6-27-26

Episode Date: June 28, 2026

How are you using AI for trip planning? Frequent Miler reader Jared wrote in:I recently asked the Bilt Neighborhood Concierge AI which weekends a particular Bilt Home Away from Home hotel (Kimpton Journeyman) had availability between August and December. It gave a useful and seemingly accurate response. Have you recently found any other good uses of Bilt's or other AIs? We’ve been answering a reader or listener question at the end of each Frequent Miler on the Air podcast episode. Now, we’ve turned the question of the week into its own weekly episode. Tune in every Sunday at 5pm for our Question of the Week podcast. And if you have your own question you’d like to submit, you can send it to [e-mail] in this episode:Check out all of our other travel podcasts from around the worldThis podcast is part of Voyascape, a podcast network that brings together the world's best travel podcasts. You can find all of our podcasts from around the world at Voyascape.com. If you are interested in advertising or sponsored content on any of our shows you can find out more at the link below.Voyascape Podcast Network

This is a Voyescape podcast. You can find all of our travel podcasts from around the world atvoyescape.com. This week's question of the week. How are you using AI for trip planning? Jared writes into the giant mailbag. I recently asked the built concierge AI, which weekends a particular built home away from home hotel had availability between August and December? it gave a useful and seemingly accurate response. Have you recently found any other good uses of builds or other AIs?

I thought this was a great question because AI is obviously a hot topic and people ask about it a lot. I think more often I get asked about it in the context of if I think it will replace what we do with frequent Myler or writing about credit cards and things. And so I think actually before I even get into how I use it, I would just say that that's not a major concern for me. I don't know. I'll be curious to hear your perspective on that before we even get into how we're using it. But I think AI has some really good strength, some things that I've used it for that have been great. I think it's greatest strength is to look through a massive amount of information quickly and give you the key highlights. It's not as good at things that are new. Like if there's a new

promotion out and it doesn't exist on the internet as widely as some of the older resources out there, it struggles a little bit with finding the latest information and reporting that kind of latest information. Also, it can't do particularly well at real world experience necessarily. It can kind of put together other people's real world experience. But if you're trying something out to see, will I actually earn points on this or will I be able to stack this deal? It probably isn't as good at those types of things. So I think that it may come for us eventually, but I think it's out there a ways of the future. So I'm not nervous about that. Are you nervous that it's coming for you? Yeah, no, you know, it's a long ways out before it can do the type of stuff we talk about correctly. So it's really good at founding correct, but often gets things very wrong. In fact, we had someone right in saying that they used AI to recommend which cards to use for different situations. And I know Stephen looked through that and found a bunch of inaccurate statements about what this person was told by AI to do. And so it'll be a while before you can get that correct. But ultimately, I think that our audience is interested, too, in our opinions about, you know, which things are best and so on.

And so I'm not worried about, you know, the frequent miler business as far as AI goes. But I think it is getting better and better. And there's more and more uses specifically for travel planning, I think, is really exciting what's possible to do with it today. Yeah, so let's talk about how we're using it. So for me, like I said, I find it really good at combing through a lot of information really quickly. And it's stuff that I could do on my own, but it would take me much longer than it takes AI to do. So for instance, we're planning a trip to region in Switzerland that has a bunch of alpine coasters, or we were planning it anyway. We ended up having to cancel this. But in the planning stages, I asked a lot about what are the best alpine coasters? What about for younger kids? What about for somebody with limited. mobility walking to the coaster from the parking lot and things like that, that AI is really good at being able to give answers that, again, I could have found with enough searching, but would have taken me much longer than it did and only took a few seconds to ask that type of stuff. And restaurant recommendations, very similar. I've been pretty impressed with Gemini,

in particular, for restaurant recommendations, for being able to drill down on things like, okay, which of these recommendations would be the best if we're going with kids? and Gemini is great at identifying, oh, this place has a kids menu or even I've been impressed when it said, well, they don't have a dedicated kids menu, but they do have some options like macaroni and cheese or this or that that are generally popular with kids.

So it's good at identifying that type of thing. And again, I could do that one by one, but I can save a lot of time by letting an AI tool kind of narrow that down for me. So I think it's good for that. It's been good for us for identifying playgrounds, actually, because when we travel, we like to hit up a playground every day or two to give the kids a chance to let off steam. I've talked about that before.

But it's really helpful to be able to just have a conversation with AI, whether that's Gemini, or I've used my meta AI with my Rayban metas, to ask it follow-up questions. Or it'll ask me follow-up questions. I'll ask, well, what are some great playgrounds nearby? And it'll say, well, are you looking for amenities like a splash pad or dog walking and stuff like that? that, again, is information you could probably find, but like the splash pad I might not have thought of myself. But if the weather is hot, that might be a great amenity to have. And so I find it useful for that type of trip planning and conversing and just asking general questions and continuing a

conversation. In doing that recently, talking about my need to to park a car for a couple of weeks near our local airport, I learned through just the conversation that there were some hotels in the area. Now, I knew hotels in the area had park and fly rates where you could stay the night and then park there for X amount of time. What I didn't realize is that some of the nearby hotels have just straight up parking rates. So you don't even need to stay. And in fact, one of them was like less than $5 a day. And it's got a free shuttle to the airport. That's a terrific deal, particularly for a longer trip. So that's something I wouldn't have found on my own because I didn't even think to ask that until I was asking about parking rates at the airport and AI suggested that there were some other

options available. So I found it good at that. I found it really bad at identifying anything time sensitive, like I said before, and also at like things that change frequently in general, like airline schedules. I was asking meta-AI for the best daytime flights to Europe recently, and it gave me a bunch of airlines and routes that don't have daytime departures. And, you know, it seemed to recognize what I was looking for because it talked about how it can be a great way to reduce jet lag to leave in the morning and get there in the evening. And there aren't a lot of options. But then it listed off airlines that don't have any. And so I found it really bad at that. Gemini was better at identifying which airlines have them or the fact that some of them are seasonal, but still not

great. It couldn't just give me the example routes and times. Like I, I, I, I, I, I was. wanted in the moment. But I find it really useful to just like walking around. I can have a conversation and learn something about my trip, my trip planning while I'm kind of doing something else. So I find it useful for that. But I think you've had some interesting mixed experiences because you wrote a newsletter recently. And I don't know if everybody read the note from Greg where you talked about this, but I really enjoyed this. And it gave me some ideas about how I might use AI for future trips. Yeah. Yeah. I've been used. using AI quite a bit lately to help with trip planning.

And a lot of things you said are very similar. When asking for recommendations for hotels, for restaurants, for things like that, the great thing is that, as Nick, as you pointed out, you can have a conversation. So you could start off with, like, you know, what's a great restaurant nearby that, you know, that I would probably like, that would be open, you know, on Monday or something. And, you know, that alone is pretty helpful, but that's something that you could do pretty easily with, like, Google Maps, for example, right? But you can turn into conversation. Like, I want one that's popular with locals and not tourists. I want one, like you said, Nick, I mean, I wouldn't be doing this, but that's good for kids.

Or, you know, maybe I want one that is something that, you know, foodies say they love. You know, that would be something more in my search criteria. And you could keep refining it that way, which I found really awesome and, you know, really led to some great recommendations that would just be really hard to do when you have a single kind of Google, old-fashioned Google search, right? It's really hard to make the search criteria right without a thing, a conversation. And time consuming, yeah. consuming, yeah. Think about like when you're looking up, you know, what's the best, whatever,

a hotel, restaurant, activity, you can see like review summaries really quickly online, but to weed through them, to find the ones that matter to you is really hard. And that's the kind of thing that AI can help with by, you know, you just ask it the things that matter to you. And it can at times do a great job of weeding through all that and finding it for you. And we've found great restaurants, great hotels, great activity recommendations. Like there was one in Dublin where we'd been told, oh, it's too late. You won't be able to get tickets to that jail thing because you have to book exactly two months ahead and it books up right away.

And so, you know, I asked Claude about it and it said, well, it's, they do release some tickets on the morning of when you want to visit. So it was morning of when I was asking about it. And so, you know, I went there and found, and I wouldn't have even thought to look for tickets that day if it wasn't for the AI actually proactively telling me stuff that I wouldn't have otherwise thought to look up, right? If I thought to look it up, I would have found it. But it just never would have occurred to me. And I have things like that happen quite a bit. Like so where it will say, you know, we'll get there before, you know, noon because of this reason.

Or, you know, caution, you know, this road is closed right now. So, you know, make plans to go a different way to get there. Things like that that, again, you wouldn't necessarily have thought to ask. So I love that AI can, when it's working right, proactively tell you stuff that is helpful. So fantastic stuff, but it absolutely does get things wrong. So apologies to those who have read the newsletter, my Sunday weekly newsletter, because I've told these stories before, but a couple little things here. First, we were flying into Barcelona, and I asked Claude AI, which what's the best way

to get from the airport to the Leonardo Royal Hotel, where we were staying for a convention. And I had done Claude because there were some things about Claude that I had found on my previous trip that I liked better than some other AIs I had tried. Like, for example, it seems to do better at incorporating conversation history. So, for example, when I had been having conversations with Claude and say, find me a restaurant near my hotel.

It just does, whereas Gemini would sometimes say, well, what hotel are you at? And I'd be like, we just talked about that. But anyway, you know, that's something that all the AIs are going to get better and better at. But anyway, so I asked Claude how to get from the airport to the Leonardo Royal Hotel. And Claude was very enthusiastic about taking the metro. It said it's a straight shot right to your hotel. It'll only take you, take you less than 10 minutes right from the airport to your hotel. Boom.

And then just to be cautious, I asked Gemini the same exact question. Gemini said, it depends which Leonardo Royal Hotel you're staying at. There are two in Barcelona. And in fact, the one we were staying at was not the one Claude assumed. And so it is really good. We did not get on the train that Claude had recommended. And so, you know, Gem and I saved my butt. But, you know, I don't think everyone would think that they need to ask multiple AIs about that kind of thing.

So that was great. Yeah, I think it's probably important in general, especially as we're in kind of a young stage of AI here, to double check whatever it's told you. You know, if it tells you that there's something that is important to you, probably should double check and make sure that that's true. It's really helpful for identifying what's probably true. But Greg's example here is a really important one that's like, but it might be way off. Right, right. Well, that example is both a great example of why it could be way off, but also a great example of how helpful it can be. Because had I just gone to Google Maps, I might have put in the default one, not knowing that I didn't know there were two different Leonardo Royal Hotels.

Who would have thought? And so I might have put in the wrong one and just followed Google Maps directions to get there. And that would have been a problem too. So it was great that Gemini was more proactive than that. Okay. So now I'm in Barcelona. Most restaurants don't open until 7 or 8 p.m. It's around 5 p.m.

I'm getting a little hungry. So I turned a Gemini now. Gemini had just saved my butt. So Gemini, hey, where can I get some food right now? I know it's early. And so Gemini's like, oh, LTO Che is nearby you. And here's all the reasons that's great and you'll love it. And I look it up on Google Maps.

It's closed. So I write to Gemini, according to Google Maps, it isn't open today. Gemini says, you are completely right. And I'm so glad you checked maps. They are indeed closed today. Good catch. So Gemini went on. Yeah.

So Gemini went on to recommend another restaurant. and I looked it up and I wrote back to Gemini. I said, Google Map says that L-58, the name of the restaurant, opens at 8 p.m. Gemini says, well, I'm officially 0 for 2 on timing today. You're completely right again. Google Maps wins. L-58 splits at shifts and doesn't reopen until 8 p.m. I apologize for the bad intel, blah, blah, blah.

And then Gemini recommends another restaurant. And then I say, again, this one's not open to date. day. And now this is literally word for word. Gemini says, I'm officially banning myself from guessing any more hours from memory. Barcelona's siesta slash afternoon schedules are a minefield, and I deeply appreciate you fact-checking me. Let's get you a win right now. I just pulled the live verified schedules for this afternoon. There's an absolute gem of a spot that is 100% open right now, highly rated by locals, and has exactly what you need. Go here right now. Bar Nuri, and it told me where to get it. And that actually was truly opened, according to Google Maps. My plans actually

changed last minute. So I didn't go there. But isn't that crazy? It took me, what, five tries to get Gemini to tell me a restaurant nearby that was actually open? Yeah, I mean, that is. It really, and it, and it's interesting that the AI apparently recognized that you were right, you know, maybe double-checked after you. You made it double-check. And I wonder now, like, playing Monday morning quarterback on this. If you had asked, can you make sure that's open right now? I wonder if it would have caught it on its own or, you know, it was just agreeing with you. You know, it's hard to, hard to know.

But yeah, I think that's a really good example of why you can't just trust. You have to like trust but verify, right? Like say, okay, this is probably good information, but I should verify and make sure it's actually open before I walk there. Exactly, exactly. So, yeah, it's still, even with that, you know, example, I'm still pretty high on the power of using AI to weed through the internet to find recommendations for things. And I think it's done a fantastic job. It's really shown us led us to some amazing restaurants that we have loved, really great hotels and things to do. All, you know,

I think we, as you said before, Nick, you could come to those. conclusions yourself, but it would take a long time and this saves a lot of time. It really does. And I think the point that you made earlier is also an important one, that it asks follow-ups or adds additional information that I wouldn't have thought to ask. And that I find is perhaps the most useful piece of it, that it thinks of the things that maybe I didn't consider, but I realize, oh, that does actually matter to me. We were looking for a place to go for my wife's birthday the other day, but we were coming from a trackmate. And so I wanted it to be casual.

and good food for the adults to enjoy, but something for the kids. And it came back and said, well, this restaurant has some outdoor lawn games. And I was like, oh, well, that's a great idea.

I've got kids. Exactly. I wouldn't even thought to ask it, which restaurants have lawn games, you know, so, great. So,

you know, that kind of thing. I find it really helpful for that. So I'm, I'm very, I guess, positive on the future of this for trip planning.

I think it's going to be, continue to be really helpful for planning, as long as we recognize the limitations. This happens. was produced and edited by Carrie Yoder, music by Annie Yoder. If you've enjoyed what you've heard today and you'd like to get more of this in your email inbox each day or each week, go to frequentmyler.com slash subscribe to join our email list. Follow us on all the various social media. Join our Frequent Myler Insiders Facebook group. And wherever you're watching or listening, don't forget to like this or give it a thumbs up. If you have a question that you'd like to be considered for a future question of the week or a piece of feedback that you'd like to be considered for our giant mailbag, you can send that to Send it to mailbag at Frequentmiler.com. Hi, I'm Mike Siegel comedian, and since 2011, host of the Travel Tales podcast. When I'm not traveling the world telling jokes for money, I'm traveling for fun out of curiosity and love of new places.

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