(upbeat music) - You traveled a lot as a solo traveler, you just got married, congratulations. I've heard you on a couple podcasts say, you know, one day maybe there's a family, I have one. How do you think that changes? Or, you know, you haven't been through it yet, but you've probably met lots of travelers.

You know, the idea of spending the afternoon kind of sitting in a bar, meeting some astrophysicists, going out to a random show, is not the kind of experience it's easy to have with, you know, young kids around. So, how do you kind of create these interesting experiences when you probably have a tighter schedule?

And you, have you thought at all about that or talked to anyone that's done it successfully? - I'd be curious actually from you actually, if you've felt, you know, as you've, as your travel style has been, has changed, how you've felt yourself adapting. I think what's exciting about traveling with kids and having kids is that you now get to instill that curiosity and that sense of serendipity in someone new, right?

And encourage that in someone and have them grow into the kind of traveler that maybe it took you longer to be. And I know that that's much easier said than done when there's like nap time and, you know, meal time and all these things that are pretty set in stone when you're traveling.

But I do wonder if there's not like, of course, yeah, you can't be like, peace out partner, I'm gonna go hang out at the bar and meet some astrophysicists, have fun with the kids. But I do wonder if there are like micro moments of serendipity that you can create, where you can be like, you know, we're gonna go for, we've rented this car, we're gonna go for a drive on this route that we've researched, but we don't know where we're gonna stop yet.

We don't know where we're gonna have lunch. We don't know where we're gonna go for a little hike. These little things that you just leave open enough so that when you do do it, you're discovering it together. You're discovering that moment together. You're having that moment of uncertainty and you're like, oh, is this the right place for the hike?

Ooh, this looks like a little intense, but then you do it together and you're like, wow, we did that, that was crazy. Remember when we did that thing? And I think I learned that from my parents too. And my parents were very good about doing that. I don't, I have like this problem.

I like, I don't remember a lot of things concretely from my childhood, but I have like vague, like more like snapshots. And I have so many like mental snapshots of family trips, of like the car pulled over on the side of the road, the physical map out over the hood of the car while my parents are like tracing our route and trying to figure out where the hell we are and where the hell we're going.

I have so many memories of us before smartphones, before the internet, pulling into hotels and like knocking on the door and being like, hey, do you have space for five at like 10 o'clock at night? Like my parents did that stuff a lot. And I think that they still, of course, their safety was the first priority when we were younger.

There was all these other needs they had to cater to, but they still kept that little bit of mystery to travel. And that little bit of, we're kind of gonna make it up as we go along. We're gonna improvise a little bit and we're gonna do it together. And we're gonna have a conversation about like, ooh, which of these two restaurants looks better?

What do you think, little Jimmy? You know, like bring them into it, bring them into that experience. So I think there's ways. I think, yeah, maybe you can't do it like you used to, fully kind of flying by the seat of your pants. But I think in micro moments and through little adjustments and through involving them in your decision-making process as you go, you can still keep that mystery of travel alive.

- Yeah, it's funny. As you were talking, I just started thinking about a trip we haven't planned yet, but different ways that we would kind of bring it to life with children. And our kids are two and two months. So, you know, we're not quite old enough to take them on all the adventures, but a few things came to mind.

One, in the last few, I don't know, months, year, we've met a number of interesting people that live in our neighborhood going to the park. Like just the park down the street from our house, we meet parents almost every time. So for some reason, I hadn't thought about it until you were talking, but I feel like we could just, if you want to meet random stranger, instead of doing it at the bar where you're sitting having a drink, which might be, you know, the solo traveler, you know, place of choice, you could also just go to a park.

You probably meet other parents. They probably have other kids your same age. You could make that your place to serendipitously strike up a conversation. So that was one that came to mind. Another thing that I think every person I know that seems to have unlocked travel one level beyond with children does is they all contact their hotel in advance or wherever they're staying and try to find some trusted source of childcare that can, not for the entire trip, but maybe help out one night so the parents can go out and have that kind of interesting, unique adventure of just walking down the street, finding a place to eat, et cetera.

- Another way to do that, and I know I have some friends with kids who have taken this route as well, is traveling with another family or another two families that are friends of yours with kids the same age. Then like you either can kind of rotate who's in charge of the kids that night while the others go out to a show or dinner or to meet people or whatever else, or you all kind of pull your money together while you're hanging out in France for some childcare that can take care of the kids one of the nights or two of the nights or whatever, and that way you're doing it together and it's a little easier.

So I know some people who have gone that route too, and I think that's a great, great way to tackle it as well. - The last one that I'm really excited about, and Japan hasn't opened the borders yet, but I'm a big fan. We've been a few times. It's like re-experiencing the places that you know a little bit, right?

Like I've never lived in Japan. I've been three or four times. I wouldn't consider myself an expert, but I do feel like I know it well enough to make it easier to kind of wander the streets and have a serendipitous experience than I would if I'd gone to Uzbekistan, which I've never been to, and I feel like I would be trying to get my bearings as well as lead the family through the public transportation.

So one thing I'm excited about is just going to places I've been to kind of share that experience and make it a little easier, right? Like the first trip with two kids running around a city, probably nice if you'd go to a place you know. Maybe you even test it out locally.

Maybe we go to New York for a long weekend 'cause it's like I know that city even better. You know, we've already tested it in San Francisco. You know, we take the Caltrain. We actually throw our bikes on the Caltrain, ride the Caltrain up to San Francisco, bike around, and then come back.

So like we're trying to get a feeling for what it's like to adventure in a city. You know, we have our own travel training wheels as new parents that we're kind of trying to take off before we take a big adventure. - But also like what a fun thing to like see a place that you thought you knew well, like to see it anew through the eyes of someone else too, right?

Like I think that's why people love taking friends to places that they love or whatever. I'm in the middle of planning a bachelor party for friends of mine, and I'm really excited that they've chosen New Orleans, which is like a city that like I love so much. And now I'm gonna be able to like see it anew through their eyes, seeing it for the first time and go to all the restaurants that I love and all the bars that I love and do all these things.

And I think that's just like such a fun thing to do. I can imagine with kids too, to like see them get excited about something that maybe you've taken for granted by the fourth or fifth visit.