Merging Into Life: Planning the Perfect Family Trip

[00:03:30] Kim: How has the shift been for traveling as a couple to now traveling with a child, with your daughter?

[00:03:37] Nik: When we decided to do that big, you know, crazy gap year, sabbatical thing, it was one of the motivations for me. It was like, you know, we’re in this window of time where we don’t have kids yet. Now’s our moment. But now that we have kids, the timing is never perfect. To anyone who thinks, “Oh, once I have kids I can’t travel nearly as much,” my big question would be: What’s holding you back? Because if it’s money, that is a separate kind of conversation, right? But if it’s, hey I’m dreading doing a long flight with a baby or a toddler. If it’s a travel safety kind of thing, I would say you might be creating problems in your mind that, don’t get me wrong, getting a toddler asleep on a long flight is such a fleeting short kind of part of the trip, and the attitude we’ve always tried to embrace is difficult things, trying times, things like that, those make way better memories and stories than when everything was perfect and comfy. We’ve had to make some adjustments traveling with kids, but it’s not been the scary, depressing, no fun kind of thing. I think a lot of people maybe make it out to be in their minds.

[00:04:57] Kim: I feel like what I hear you saying is that there is no perfect moment to travel with your kids, and you don’t necessarily have to wait until they’re older to do it.

[00:05:05] Nik: You know, the saying goes, life is hard, and the response is compared to what? I kind of think the same about traveling with kids. It’s like traveling with kids is so hard. And my response is, well, look, if you’re going to have to be changing diapers and wiping noses anyways, why not do it in Italy?

[00:05:25] Kim: I know that right now you’re currently planning a trip for your parents’ 40th anniversary, which is huge. What has it been like being in charge of the planning of big a multigenerational vacation? Like what’s been the biggest challenge that you’ve had so far in that?

[00:05:40] Nik: One of the challenges has simply been adapting to and understanding everyone’s tastes and preferences. I would say, you know, if someone finds themselves in a similar situation, where maybe they’re planning a multigenerational type of trip, getting on the same page about what is the type of trip everyone is wanting to take, is probably the hardest conversation to have. The immediate follow-up to that is what are everyone’s budget expectations, right? Because I came from the finding cheap flight deals via email world. My baby boomer parents have more money than me. Like they just do. And I think like a lot of people kind of my age would find themselves in a similar situation, so the tastes could be very different. And so, the challenge there is simply can we all take a trip we want to take at a budget we can all agree on?

[00:06:35] Kim: So, we were just talking about challenges. So, now I want to ask you, what is something unique or meaningful about traveling with multiple generations, especially when you’re trying, like you said, to make it work for younger kids, older kids, maybe grandparents as well?

[00:06:53] Nik: To get to see your own kids sort of experience something new and see it through their eyes how they react to it, that is, I think, the most powerful piece. So, more practically, for the grandparents, it’s simply just getting to spend more time with the kids and grandkids. I think, as you age, you just really start to think more about those things. And then, selfishly, pragmatically, for us young parents, honestly, just having an extra set of hands, like they say, many hands make light work, and it is so true. I am such a fan of group travel right now while we’ve got a rambunctious toddler.

[00:07:29] Kim: Yeah, it takes a village, right? I know that traveling with kids obviously changes the pace of your trip a little bit. So, what expectations do you think parents need to adjust to when they’re bringing kids or maybe even grandparents on a trip?

[00:07:47] Nik: I think the biggest adjustment for us has been, No. 1, expectations around attractions. We like to go to museums and try and absorb a lot of info while we’re in a place. It’s not the only thing we do, obviously. But the amount of time we can spend in a museum right now with a 2-year-old, way smaller than when we first started traveling. We’ve gone from, hey, as a couple, we’re going to like three or four different museums to maybe we’re going to one. Now we’re more likely to prioritize that kind of science museum that has some fun interactive stuff for kids. The other thing to think about is around nighttime, nightlife. If you have a kid with you, bedtime is going to come. And so that’s a big part of it. The other things we’ve had to build in is to accommodate for nap time. We’re typically planning to go back in the middle of the day to put our daughter down for a nap. In some of the group travel we’ve done with our daughter, I’ve had to kind of set those expectations with the others that are with us. The only other thing I’ll say on that is, which is quite a bit different than when it was just the two of us, is planning for downtime in general. If we’re taking a 10-day trip, instead of every single day, we’ve got this kind of itinerary, and we’re moving locations every two or three days, we’re trying to just build in more rest days generally, because she needs to be able to run around. We kind of need to be able to relax a little bit more.

[00:09:20] Kim: I wanted to briefly go back to expectations because you said something in one of your videos I thought was really interesting. And you were talking about how sometimes parents can have expectations and maybe some assumptions about a place regarding kids, but that may not be true.

[00:09:40] Nik: My mindset at least, and I think a lot of Americans, go in expecting that people are going to be annoyed you have your kid with you. That just really hasn’t been our experience. I have found most of the places we have been to be just as if not more family friendly than the U.S.A. And what I don’t mean is, oh, because they have way more playgrounds. I don’t mean that, those things are more child focused. What I mean, these places to me have felt more family focused and more like families were a priority. Even when we’re in a restaurant or something, a waiter going out of their way to bring our daughter a dessert on the house or something or try to make her smile. We had a couple of recent experiences. Portugal knocked our socks off in terms of like how kid and family friendly they are there. They love kids. We were in Sintra just outside of Lisbon. It was one of our last days of the trip. And there was just this absolute mob of people waiting to get on a bus. The bus driver saw us. We weren’t anywhere near the front. He parked his bus, got out of his seat, came to the back door of the bus, pulled us out of line and said, “you board first.” He closed the doors behind us. And then, he said, “families are a priority here.”

[00:11:02] Kim: It kind of also goes back to what we were saying about it takes a village and having community. And sometimes that is also people that you don’t know, just people living in that city or the community that already lives there can also be part of your village while you’re traveling.

[00:11:17] Nik: For sure, we met awesome people before we had kids while we were traveling, but I would say we’ve had way more of those kind of kindness of strangers sort of moments with our child. And this is the other reason why people shouldn’t be worried about traveling with kids. It’s one of those irrational fear kind of things. Our species makes children all over the world. You know, there are kids everywhere. If you run out of diapers, you’re going to be able to go get them at the grocery store. It’s the most relatable thing on planet Earth, seeing a parent with their child.

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So, let’s talk about some practical tips. When you’re planning a multigenerational trip, where do you suggest someone starting? Should they start with the budget, destination, accommodation?

[00:12:38] Nik: The first place I would start, 100 percent, is aligning on where to go. A common mistake I see when it comes to Europe travel specifically, trying to cram too many destinations in. And there’s that mindset of, well, we’re already taking that long flight. We’re already over there. Why not hit a bunch of, you know, so we got to do London and Paris and Rome and Amsterdam. And that was a big sort of coaching point with my parents. It’s, listen, you are going to have such a better time if we can pick, like, two places or maybe just like one region and then sort of go deep in exploring that. First, is getting clear on where, right? Then, I would ground that very fast in looking at flights. The flights is where it gets reeled. If you can be flexible even by just a day or two, sometimes that can save you hundreds, maybe thousands of dollars. So, you got to appoint kind of a money person in your crew. Once you know the flights, then it gets much easier. You’re setting kind of basic day-by-day flow of, all right, here’s the places we think we’re visiting. And then this is where I tend to hand things off to my wife a lot of times. Like, I’m the big logistics guy. She helps us make the trip fun. What’s a cool experience or tour we could take together. What’s an amazing highlight I would love us to be able to look back on.

[00:14:04] Kim: So since you are more of the analytical guy, what do you look for in accommodation when you’re traveling with multiple generations?

[00:14:16] Nik: Typically, if we’re doing more than just our core family, we’re almost always looking at, hey, could we do a short-term rental with multiple rooms, preferably multiple bathrooms? The problem with hotels, you’re really not hanging out with your group. It’s only when you’re out doing the stuff, but having an apartment, a short-term rental, whatever it is, you have that shared space, right? So, you get to hang out and everybody gets their own bedroom and can have their own private time, but it’s awesome to be able to, especially if you have young kids with you and you need to kind of get in early for bedtime, well, then the adults are hanging out in the living room. Those are some of the great memories on the trip, too. It’s not just in all the photogenic Insta-worthy spots.

[00:15:04] Kim: So let’s talk a little bit about packing. What are your go-to tips for packing efficiently for yourself, for your toddler and also for the whole crew?

[00:15:17] Nik: It’d be four things. The first is make a list. Before even touching your bag, make a detailed list of what you need. I am one of those people that, in the hours leading up to a trip, I’ll start to have these like what ifs creep in. And what I’ve found works great for me, if you’re that kind of person, you could always do a test pack, right? Maybe pack your bag like a week, two weeks before the trip? And then live out of it for a few days. That’s a really fast way to realize, oh, I’m forgetting something or, oh, I haven’t used this at all, right? So, make a list, think about what you’re actually going to need.

And so, then, in terms of how you pack, we’re big on compression packing cubes, group like items together and then compress them down. Packing cubes are a great way to save space. And you don’t even, you don’t have to spend a bunch of money here. Like for years, I used gallon sized Ziploc bags. Those work great too, because you can press all the air out of them. It groups your stuff together.

In terms of nifty hacks, we always plan to have a midway laundry stop on our trip. And to me, like that is one of the ultimate ways to pack less. When I say laundry, people roll their eyes, and they go, “oh, I don’t want to do laundry on my trip.” But here’s the deal, you’re not doing a massive load like you are at home. You didn’t bring that much with you to begin with. If you’ve planned to pack light and do laundry along the way, and if you stay in a rental that has a washer, it is really not that hard to throw a few pieces in the wash in the morning and then hang them up to dry overnight when you’re back in for the day.

A couple of just like toddler specific things, I’ll throw in our travel stroller. And I would say this is probably one of the most important purchases you’ll make. It’s this travel stroller with the touch of one button. It collapses down very kind of flat enough that it can go through the conveyor belt at TSA security. But it is a champ on cobblestones, sidewalks, and it’s really good for, hey, you’re hopping on a train. You’re getting on public transport. We can grab her out of the stroller and then one button, boom, it’s collapsed down, it goes into the luggage area. That is by far our No. 1 recommended travel item.

[00:17:43] Kim: Love that. Thank you so much for sharing those tips. I know that you are a big points and miles guy, and I’ve watched your video of you flying Emirates first class on points and miles, which was awesome. So can you just share with us maybe one or two tips for using rewards to help offset travel costs for big group travel?

[00:18:05] Nik: Well, points and miles were a huge reason we were able to do that. And I was tallying it up not long ago. Points and miles covered about $37,000 in travel experiences during that trip. So, if you know how to redeem well, it can be a huge money saver. In total, points and miles has saved me over $150,000 in travel expenses. So, the really simple version of this is, for anybody listening in disbelief, because I was you a few years ago, you’ve probably already taken a flight or you’ve heard the pitch. Most credit card companies offer some kind of signup bonus, like, 60,000 points, 100,000 points if you spend a certain amount of money in the first few months. That’s not a scam. That’s real, right? So, the trick here is sign up for the card, but don’t go spend a bunch of money on stuff you don’t need. Use that to pay for your actual life expenses. All the points and miles we’ve accumulated has come from paying our bills. Look for opportunities to meet these minimum spends. That is the biggest way you’re going to earn a lot of points.

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[00:19:20] Kim: For someone listening who feels nervous about coordinating a big multigenerational trip, what’s your biggest piece of advice?

[00:19:30] Nik: I would say just begin with the end in mind. Why are you doing this, right? Because it’d probably be easier to travel without your family. Probably the reason someone would be considering doing this is in creating some shared memories. Just know going in something is going to go wrong, right? So, think about that, that shared trial, that shared frustration. With travel being kind of that shared purpose for my wife and I, I would say 75% of the funny stories we recount, we think about is somehow relating to, you remember this crazy thing that happened? There was a quote that really inspired me when we first launched our channel. On your journey through life, make sure your story has at least one extraordinary chapter. I think travel is such a beautiful way to do that. And if you’re trying to write a story that includes your family, includes other loved ones, this is such a powerful kind of like accelerant to creating that possibility for you.

[00:20:30] Kim: I love that. Nik, what’s the best way that our audience can find you?

[00:20:35] Nik: The best way is check us out on YouTube. Our handle is Away Together. That’s really the best place.

[00:20:58] Kim: Thank you Nik for sharing your story with us and for kind of reminding us that you can plan a good trip with toddlers, with teens, with grandparents. So it is possible. So thank you so much.

[00:21:11] Nik: Absolutely. Thank you for having me. It’s really worth it.

[00:21:17] Kim: Big thanks to Nik for showing us that you really can plan a trip that works for toddlers, teens and grandparents without losing your mind. A good trip isn’t just about where you go, it’s about who you go with and how you show up for each other along the way. If this episode helped you rethink your next family trip, leave us a review, share it with someone planning their own reunion, and we’ll catch you next time on Merging Into Life. The views and opinions expressed in this podcast are not necessarily the views of AAA Northeast, AAA and or its affiliates.