By Rishika Sharma, on January 9, 2023

Family travel hacks: How to plan and book group trips like a pro

Every group of friends has one and every family too. That booking wizard. The golden individual who’s always responsible for booking their parent’s trips to Europe to see the grandkids or the one who plans the entire gang’s getaway to Cancun. And with the holidays just around the corner, if the designated vacation planner in your circle hasn’t been crystalized yet, you might find the pressure on YOU to deliver. After all, as an avid listener of Out Travel The System, you’re the one in-the-know on how to hack the travel game, so it’s only fair you put all the tips and tricks you’ve learned to good use.

For Nevin Martell, not only is he the group and family trip planning pro in his group, but he’s also the family vacation planning expert for the whole of America. No ordinary travel writer, he has carved out a specialty covering family travel for the likes of The New York Times, USA Today, and National Geographic.  We caught up with him ahead of the end-of-year holidays to understand what the vacation planner of the group should be considering and how to take the stress out of family vacations. Here are Nevin’s top tips:

Get transparent about money

The main point of discussion needs to be about price because you don’t want to book people into accommodation that is out of their budget, yet you also need to find somewhere that everyone is comfortable staying. Otherwise, the trip is not going to be enjoyable.

The key is finding a comfort level for everyone. You don’t want an individual racking up a whole bunch of credit card debt because everyone else wants to stay in a more luxurious property, so if you do want to stay in a nicer house, the group should consider stepping up and chipping in a bit more to accommodate for the family who can’t pay as much. That way, it’ll be worth it for all of you. 

Adjust the planning depending on the size of the group

For my immediate family, my general rule is that every day there’s something that will really appeal to either my son or my wife. For example, our son’s a vegetarian, so every restaurant we go to must have a strong kid-friendly vegetarian option. Or, as my wife is not a huge fan of extreme sports or adrenaline junkie-type of stuff, I avoid booking those types of activities because I don’t want to put her in a situation where she’s going to be stressed out or anxious by an activity.

However, when it comes to extended family vacations, because there are so many people to take into consideration, I pick the destination and help with where we’re staying and then give options to people so they can choose what they want to do when they get there. 

It’s not ‘my way or the highway’

Sometimes it can be hard to coordinate a group trip. With friends, it can be effective for one family to book a trip or plan a trip and then tell the others, “This is the plan, come if you want,” but with family trips, tread more sensitively.

While it can be tempting to just stick your marker into the sand and waltz off into the sunset with no-one else joining you, that’s not what a family holiday is about. That’s just you on vacation by yourself. Having said that, a family vacation shouldn’t mean forced family fun either. The whole point of a family trip is not just to see a place and to experience things, but it’s about spending quality time together through experiences together and also allowing for people to have time on their own or to do the things they want to do. That’s what will make it more enjoyable for everyone, and it’ll ensure you conduct yourself well too. You want to approach it so the trip goes well for everyone and leaves that “Let’s all do this again” feeling.

Bond over shared new experiences

Plan just enough so that there’s flexibility in your schedule and there’s time for people to just enjoy a place at their own pace and do what they want to do. 

Also, I recommend picking activities that are both within people’s comfort zones, and also slightly out. It introduces them to new things, whether that’s new cuisines or a new kind of adventure. 

Split by room

Another tip would be to consider splitting by rooms rather than by individual families or groups. You don’t want the family of six that’s taking up two or three rooms to pay the same as your single aunt. 

Do the opposite of everyone else

For trips around big holidays such as Thanksgiving, Christmas, summer, etcetera, I try to think of the places where most people won’t be visiting, or where they will be going, or what they’ll be doing, so I can plan the opposite. I also think about where it could be shoulder season. For example, we went to New Orleans one year during spring break, and it was perfect because we missed Mardi Gras and all the big parties. Instead, we got to experience the city in its natural state, without all the crowds at restaurants, hotels, and cultural institutions, and minus the hiked-up prices too. 

Get the group’s buy-in

On the topic of finding accommodation that everyone is comfortable with, you also need to have everyone review and pitch in. I also look for amenities that will work for different ages within the group. For example, if we’re staying at a hotel, I’ll make sure there’s a water feature, so either a nearby beach or hotel pool, or if it’s winter, then I’ll look for something like a hot tub. You want to make sure there’s stuff for people to do when the kids don’t want to go out that day or somebody just wants some alone time.

Know when to take a break

The gold standard, of course, is looking for activities that everybody’s going to enjoy, but that’s not going to be the case with every activity that you book. So try to make sure that the agenda rotates between doing big things for different people. I also try to book one big activity a day, because my experience in traveling with kids has taught me that if you do one big thing in the morning and one big thing in the afternoon, you’re burned out by the afternoon. Or, if the one in the morning runs late, then it becomes problematic and stressful. 

Additionally, I recommend trade-offs. For example, my family and I went to Mexico City a few years ago, and I wanted to experience a specific Michelin Star tasting menu, which was going to take three hours. So I went there and did that myself, while my wife was with our son. And then on another day, my wife wanted to go to a specific exhibit, which I would have also liked to visit, but that was her solo thing on the trip while I did something with our son.

Roll with the punches

Traveling with toddlers and young kids doesn’t have to be scary, nor a big deal. OK, so your kid cried on the plane the whole time and annoyed other passengers, or you have to change diapers in the strangest places at the most awkward times. But you’re going to have to deal with things like that anyway. That’s just part of parenting. I think you might as well be doing other interesting things in interesting places while meeting interesting people while all that parenting is also taking place.

I understand it stresses people out, but I think traveling with kids is great for both the parents and the kids in the sense that it teaches you a sense of flexibility and resilience, which are great life skills for both.

For more tips, listen to the episode here or read the full transcript. If you’re the vacation planner of the group and you have additional tips for us, DM us. We’re @expedia on Twitter and Instagram. And let us know where you end up booking for your group. Tag us in your photo and put #ExpediaPic in the caption

Want to learn more?

Listen to the podcast now, check out the complete transcript below, or catch the full conversation on Spotify or Apple.



Nisreene Atassi, Expedia Global Head of Social Media, and host: I’m Nisreene Atassi and this is Out Travel The System. This week we’re talking about what to consider when planning family vacations, how to avoid itinerary stress, and balance everyone’s needs. We’ll talk trends…

Christie Hudson, head of Expedia PR for North America (sound bite): You can actually save between 20% and 30% just by departing on the Monday before the holiday instead of over the weekend. And to avoid crowds, avoid the day before Thanksgiving – the busiest travel day of the entire year.

Nisreene: ..hear from travel writer, parenting journalist, and author Nevin Martell…

Nevin Martell, travel writer and parenting journalist: I think traveling with kids is great for both the parents and the kids in the sense that it teaches you flexibility. You have to be really resilient. It teaches great life skills for both the adult and the child in the situation.

Nisreene: ..and really get down to business.

Nevin: With family, I think you have to be much more delicate, because a point of a family trip is not just to see a place and to experience something, it’s to spend time together as a family. If you’re just going to stick your marker in the sand and, like, waltz off into the sunset and no-one joins you, that’s not a family vacation.*

Nisreene: Here we go!

[Musical interlude]

Nisreene: Today we’ll be talking about planning your next family vacation that will be sure to accommodate everyone’s needs – from the children to the grandparents and everyone else in between. But first, let’s hear the trends. All right, Christie, what’s up for this week?

Christie: Holiday travel can be a bit daunting, to put it mildly. For the past 15 years, I’ve traveled for the holidays every year but one – during the height of COVID. And six of those years, we’ve had small children in tow. So you can trust me when I tell you that this, too, can be hacked. But before I get into the cost-saving tips, let’s talk a little bit about where people are headed. When we think about Thanksgiving travel, we often think about people traveling to see family or heading home for the holidays. Well, that’s not really what the data shows this year. The most popular destinations for Thanksgiving 2022 are Cancun, Orlando, New York, and Las Vegas. Those don’t really scream Grandmother’s house, do they? Clearly people are taking advantage of the holiday break to enjoy a real vacation. Whether it’s warm weather by the pool in Mexico, a trip to Disney World with the extended family, or living it up in Las Vegas, travelers are cooking up something a little less traditional this year.

All right, so let’s talk about holiday travel tips. First, here’s what Expedia traveler data is saying about holiday travel for 2022. Airfare is pricey. The combination of strong traveler demand and airlines not fully up to their pre-COVID capacity levels means that ticket prices are higher than normal for the holidays. So the key to saving a bit of money on airfare is to be strategic about your travel dates. You can actually save between 20% and 30% just by departing on the Monday before the holiday instead of over the weekend. And to avoid crowds, avoid the day before Thanksgiving, which is not only the busiest travel day around the holidays, but also the busiest travel day of the entire year. Finally, one more tip for you if you’re flying this holiday season. According to Expedia’s Air Travel Hacks Report, flights that depart after 3 pm are 50% more likely to be canceled. So take the earlier flight and you’ll get there in time for turkey dinner.

[Musical interlude]

Nisreene: My guest today is travel writer, parenting journalist and author Nevin Martell. Nevin is an expert in planning family vacations and a strong proponent of traveling with children, which I love. His work has appeared in The New York Times, National Geographic, Fortune, USA Today, and many more. Can traveling with the entire family be a breeze? Let’s find out.

Hi, Nevin. Welcome to Out Travel The System. It’s so great to have you.

Nevin: Nissi, thanks so much for having me. I’m super stoked to be here.

Nisreene: So you’re, like, a family travel planning expert. I love that.

Nevin: It’s a job that I’ve taken on because I love travel. I’ve loved travel since I was a little kid. I went on my first trip when I was six months old, and I always knew that when I had my own family, I was going to drag them around the world the same way my family dragged me around the world when I was growing up. And it’s just a real pleasure to get to travel with the ones you love like that.

Nisreene: You know, I read captions all the time about people, like, talking about when they’re preparing to travel with their loved ones, they’re in, like, total survival mode. They’re like, “Okay, I was able to pull it off. We did it. We made it to the end.” Why do you think family travel planning is so anxiety-inducing? I mean, like based off of – you’ve got your professional experience and you’ve got personal experience. What is it that creates just so much stress for us when we’re trying to do this? Because we know the benefits of it, but it’s still, like, it’s become so stressful.

Nevin: Well, you’re basically taking the people that you love the most and putting them into, like, cramped quarters and unsure situations and throwing in a whole bunch of, like, chance, both good luck and bad luck. You know, it’s a… you’re put into, like, a boiler room, almost, with them when you travel, because there’s only so much you can control. But travel is also about letting go of the idea of control. But, of course, the people that you love just want you to say, like, “Well, this is where we’re having lunch, and then this is where the snorkeling expedition is, and later on this is what we’re going to be doing,” and everything’s going to go perfectly. But that’s not the way that it ever goes. And, you know, kids have high expectations of you, spouses have high expectations of you, and it can be a real recipe for disaster. So I understand why people really, really stress out about it.

Nisreene: Yeah. I think from my personal experience, when I get the sense that my daughter’s, like, not having fun or my husband makes a comment about something, I get… I’m so sensitive to that, because I feel like it’s completely on me to make this trip the best it can be. And so any, like, sense of dissatisfaction is so gut-wrenching. Do you agree? Do you feel like that happens to you as well?

Nevin: Oh, my God. I take it so personally, because you spent all this time researching, you spent all this time booking, you spent all this money, and then when something doesn’t go right or something isn’t the way you thought it would be, or it doesn’t land with a spouse or a child the way that you thought it would… So I do take it very personally, but I try not to show how much I am taking it personally in the moment. And also, you know, then there’s the question of like, you know, “Why are we doing this like this? This isn’t that cool.” And you’re like, “Trust me, I looked at every possibility for today and this one looked like the best use of our time, given what we wanted to do in our budget.”

Nisreene: Do you approach travel planning differently when you’re looking at planning a trip for, like, your immediate family versus your extended family?

Nevin: Absolutely. I mean, my immediate family, my general rule is that every day there’s something that will really appeal to either my son or my wife. You know, also something that will appeal to me, usually. But I want to make sure that they’re happy. When we go out to eat, our son’s a vegetarian, and so, like, every restaurant has to have a strong kid-friendly vegetarian option that they’re going to enjoy. You know, my wife is not a huge fan of like, you know, extreme sports or adrenaline junkie type stuff. So I would never, ever book something like that on our trip. Though she surprised us and when we were in Taos, New Mexico, she actually wanted to do a hot air balloon, which we ended up doing and we all loved. But I – she was like, “Why didn’t you suggest this?” And I was like, “Well, you know, I don’t want to put you in a situation where you’re going to be stressed out or, you know, freaked out by something.” But, then, when it comes to the extended family, you know, that’s so many people to take into consideration. So for an extended family plan, I really just like to pick the destination and help with where we’re staying and then give options to people. And people can kind of do what they want when they’re there.

Nisreene: Yeah, I think that’s a great tip. So, like, sort of adjusting how in-depth your planning process is based on how big or how well you know the group that you’re going with. That makes a ton of sense to me. And I feel like just this idea of not trying to force everybody to do everything all together all the time is probably a way to reduce some of that planning anxiety, because then it’s kind of like a Choose your Own Adventure.

What about choosing hotels? Like, what tips do you have for that? Especially when you’re looking at sort of large, you know, large groups, different budgets. How do you sort of alleviate the stress when you’re picking your lodging? Do you typically do vacation rentals? Do you typically do hotels? Like, do you call, like, a planning meeting together with your family? How do you choose the lodging bit or do you just do it solo and everyone trusts you?

Nevin: No. Again, you have to have buy-in from everybody, because you don’t want to book people into accommodation that is going to blow out people’s budget or be beyond what people are comfortable with, or, again, put them in a situation where they’re just not going to enjoy it. I find when traveling with big groups that, you know, something I always look for, whether we’re renting a property or we’re at a hotel, you know, a water feature, whether it’s on the beach or it has a pool, if it’s that time of year. If it’s in the winter, if there’s a hot tub. You know, that’s always a great feature for every age group in the family. The other thing I look for is, you know, you look for the general amenities of a home or of a hotel. You know, you want to make sure there’s stuff for people to do when the kids don’t want to go out that day or somebody just wants some alone time. Like, make sure there’s activities at the hotel or close to the house that they can, you know, just take advantage of. That’s really important. And, of course, you know, reading all the reviews, if you’re doing a rental property, so you don’t find out that the owner’s living in a casita on the back end of the property when you all arrive or something like that, you know?

Nisreene: Yeah, yeah, totally. I want to… you mentioned the budget thing and sort of splitting money and that kind of stuff. And I want to sort of dig in a little bit more on that one. So, one, how do you recommend people split up a budget for a vacation rental? Is it based on… because, especially when you’re traveling with a lot of people, let’s say you’re getting this amazing place. Do you recommend people split it by rooms, right? Because, like, this family needs three rooms, that family needs two rooms, that type of thing, or they’re going to share a room. Like, how do you recommend people split that up? And then my part two to that question is how do you even begin to broach the subject about money and spend with family so that everybody feels like that they can share what their real comfort zone is, I guess?

Nevin: Yeah. I think that approaching the split of a rental property or wherever you’re staying by room is great, because you don’t want your, like, single aunt to have to pay an equal sum as the family of six that’s taking up two or three rooms. I think by room is a great way to do it. If – you know, everybody doesn’t want to talk about money, but everybody should talk about money, you know, and transparency when you travel, when it comes to the budget, is really key to a happy trip for everyone, because you don’t want somebody, you know, racking up a whole bunch of credit card debt with that rather than just saying, like, “Hey, this is out of my comfort zone as far as the budget goes.” So if you do want to stay in a nicer house and, you know, you have the extra money, step up and chip in more for the family that doesn’t. Everyone will have a – you know, it’ll be worth it for all of you.

Nisreene: Okay. Do you feel like there’s a sweet spot on the max number of family members that you should travel with, especially when you’re, like the planner? Like, for you, do you have a threshold? Are you like, “I will not plan on family gatherings over ten people,” type of thing?

Nevin: I think four families within a larger family is, like, pretty much my max, because that’s the most you can – you know, you can fit that in one or, like, one very large rental property, or two that are next to each other on a cul-de-sac or whatever.

Nisreene: Oh my God, it’s a nightmare. Yeah. I was having a conversation on the show with somebody previously, and it wasn’t… it wasn’t about family travel, but we sort of got on the subject of when you’re trying to plan travel with your friends, it’s all just really theoretical until somebody just says, “Hey, I’m going here in this week. If you want to come, let me know.” Do you feel like that kind of tip sort of stands for families as well, or do you feel like you have to be a little bit more thoughtful about it? Like – and how do you kick off those conversations? Are you doing email, like, group chat? Are there any, like, tools or apps that you’ve used that you find to be really helpful? Because I feel like that happens a lot with me and my family, especially, like, my sisters. We just… we chat, we’re like, “Oh, we should do a spa weekend getaway. Oh, that’s great, let’s do this.” But, like, it really only happens when someone says, “Hey, I’m going to go here for this long weekend. If you’re in, great. If not, see you next time.”

Nevin: “We’re going to go this week. If anyone else can join us, it would be awesome. If not, so be it.” With family, I think you have to be much more delicate, because, you know, a point of a family trip is not just to see a place and to experience something, it’s to spend time together as a family. And, so, if you’re just going to stick your marker in the sand and, like, waltz off into the sunset and no-one joins you, that’s not a family vacation. That’s just you going on vacation by yourself.

Nisreene: So what, from your experience, have been some of the best sort of family destinations for holidays that you’ve seen? Or what are some of the most important tenets that you think people should look for when they’re planning, or when they’re choosing a destination?

Nevin: Yeah. I mean, holiday destinations, you know, if we’re talking the year-end holidays, somewhere warm always goes over well. You know, if you want to get to Central or South America, the Caribbean, you know, no family is going to complain that, you know, a day after Christmas or Passover, you’re going to hop on a plane and go to Hawaii for a week, or go to Nevis, or go to Mexico. Like, that always goes over well. If you want to stay, you know, on the continent, you know, you can always embrace the snowy side of life at the holidays and just do a ski trip or, you know, do something that’s going to take you to, you know, the Midwest and really enjoy snowshoeing or cross-country skiing, if that’s more your speed. But what I always look for is kind of like counter-programming. Like, when we’re going on spring break as a family, you know, I, of course, don’t want to go anywhere that’s like “Spring break USA” with my wife and now our nine-and-a-half-year-old. So, for example, we went to New Orleans one year during spring break, which was perfect because we missed Mardi Gras. We missed, like, all the big parties in New Orleans and we got to experience the city, you know, kind of in its natural state. And that was the best time I could have thought to take my family to New Orleans at this stage in my son’s life. Don’t go where everybody else is going. You know, think about the places where it might be shoulder season so that you’re, you know, at the tail end of people coming or, you know, the beginning of people coming, but it’s not overrun. Not only will you have fewer people to deal with, but you’ll get better rates and you’ll have easier access to all of the activities and cultural institutions that you want to go to. So that – I always try to kind of think what a lot of people are doing, and then I try to do the opposite.

Nisreene: That’s smart. Especially because if you have a bigger family, as well, when it’s super-crowded, it’s impossible, I feel like, to go out to dinner, getting reservations, getting cars. Like, it all just adds to the stress when the destination that you’re in is also a super, super busy place. I always love the tips for traveling with shoulder season. Which is tough when people, when kids are in school, but if you can swing it, it’s always a great tip for sure.

Nevin: Yeah, it’s always shoulder season somewhere. You just – it just might take you a lot longer to get there than you want to.

Nisreene: How did you start actually making this a career and start writing and becoming this expert in family travel?

Nevin: Well, I started early. You know, like I say, I took my first trip when I was six months old and we went to France, my mother and father and I. And I have absolutely no memories of the trip. I have some great pictures from it. But from that point on, you know, we traveled a lot, growing up. We did a lot of the South Pacific, we did a lot of the Caribbean, we did parts of Central and South America. And, so, travel was just something that was a part of my life as a child and I always loved. And when I became an adult and had my own family, you know, I knew that I wanted to share that with them. And, so, ironically, kind of my first foray into travel writing was right before my son was born. My father and I took a trip to Costa Rica as a bonding trip. We went back to Lake Arenal, which was a place that my father had been to, like, before I was born, and he had loved it and had always wanted to go back. And I’d been to Costa Rica a couple of times before, but not to that particular part. And we decided to take this epic, you know, kind of fishing trip there. And I wrote a story about it for the Washington Post travel section, and it got picked up and syndicated in a lot of other newspapers. And, you know, I really enjoyed the experience of it. And then we had our son and I realized that I couldn’t be on the road as much as I would need to be in order to be a travel writer. So I waited about three years until our son, you know, was up and running, so to speak. And then I started just traveling more and writing about it. And I had already been writing about food for a number of years and parenting. And so a lot of my travel writing kind of combines my love of food and focus on family. And so, yeah, I’ve really been able to carve out a little bit of a niche for myself as, you know, a family-focused, food-focused travel writer.

Nisreene: You’re living the dream, Nevin! You’re living the dream. Like, it’s so great. I love that for you.

So you started traveling with your son when he was around three years old, which I feel like is a very tough time to travel with kids, because toddlers are, like, really tough in general – the threenagers. Why shouldn’t people be afraid to travel with toddlers, particularly around the holidays?

Nevin: Sure. I started taking travel-focused trips for work on my own when my son was about three. But we traveled with them first when they were about half-a-year old. And, you know, everyone talks about the terrible twos, threenager, etcetera, etcetera. I can’t claim that we ever had those experiences with our son. I think traveling with kids is great for both the parents and the kids in the sense that it teaches you, you know, a sense of flexibility, a sense of… You know, you have to be really resilient, you have to be really smart. You know, it teaches great life skills for both the adults and the child in the situation. And so, I would encourage people to do it, you know? Yes, your kid is… My kid cried on the plane all the time and annoyed other passengers, myself included. Like, we had to change our son’s diaper in the strangest places at the most awkward times, you know. And, like, who wants a blowout in the middle of LEGOLAND? Nobody. But you’re going to have to deal with it. Like, that’s just a part of parenting. You might as well be doing interesting things in interesting places while meeting interesting people while all that stuff is unfolding. I understand it stresses people out or people are hesitant to do it, but get out there. You know, the world is not going to wait for you. You got to go out and experience it. And it’s a good lesson for your kid too.

Nisreene: So for your writing, what is really the source of the inspiration for your family travel?

Nevin: You know, I do a lot of research – both talking to people that have been to a destination that I’m going to, people that I know from that destination. I spend a lot of time online going down Instagram rabbit holes, you know, and other social media rabbit holes. I read a lot, you know, in terms of both what’s in print and online. It’s kind of split between what I find in my research and what I experience in the field, because oftentimes you’ll have what you think is a great idea for a story and then you’ll go to a place or have an experience and it just won’t be what you expect it to be or what you plan on pitching an editor on. But then something else will happen or you’ll meet somebody else and it’ll just be, you know, an unexpected great moment in your trip and you’ll be like, “Oh, that’s my story.” But you won’t have that moment unless you’ve put yourself out there, unless you’re on the ground and you leave yourself open to those kinds of possibilities.

Nisreene: Well, so, what info have you gotten that has been, like, the best? Like, what tips have you gotten from people that have really sort of stuck with you the most?

Nevin: Well, I mean, like, so I went to Tulum right before the shutdown, and the first night – or I think it was the second night – I had a dinner at this high-end restaurant and the chef had worked at Noma, and it was an amazing meal. But my first question for him is like, “Okay, so where do you go for tacos when you get off work?” And he gave me the name of this taqueria in town that, you know, you could have driven by and not seen. And I went, like, four times when I was there. They were the best al pastor tacos I’ve ever had and they were a pitingly small sum of money for each one. But, you know, then the next time I interviewed the next chef at the next restaurant, I asked him for his taqueria recommendations, I found another amazing, like, roadside taqueria – some of the best food, at both those places, I ate the whole trip. I was staying in a hotel and I asked somebody like, you know, “What’s something that you know?” The question I always ask is, “What’s the thing that locals do that tourists never get a chance to do, or never do?” Yeah, he turned me on to this amazing cenote – these sunken, you know, pools.

Nisreene: Caves, yeah.

Nevin: There are a lot of them in Tulum. Most of them are totally commercialized and, you know, overrun, and very – you know, you buy a ticket, and you can zip line over it. He turned me on to one that, you know, nobody was going to and was, like, in the middle of the jungle and was, you know, the real cenote experience. That was phenomenal. Sometimes you find – I find the best coffee on my trips, always, from asking people in hotels, you know, “Where do you go for coffee?” or asking a driver. Drivers always know the best cheap eats and good coffee shops. So, you know, I’m always… Like, I’ve usually planned out my cultural experiences, but finding good niche food and good local food and coffee always comes from talking to people on the ground.

Nisreene: Yeah, no, I agree with that for sure. I want to talk about activities. How do you sort of tackle planning activities for your kids while still giving parents time to sort of relax and things like that. Or, like, do you try to find activities that both the parents and the kids will enjoy? Like, what are your recommendations?

Nevin: Yeah, well, you know, the gold standard, of course, is an activity that everybody’s going to enjoy. But that’s not going to be the case with every activity that you book. So I try to make sure that, you know, it kind of rotates – that we’re not doing two big things for me back-to-back, or even for our son back-to-back. So, you know, what I really try to do is say, “Okay, today we have one big activity.” Like, I try to book one big activity a day. If you do one big thing in the morning and one big thing in the afternoon, which is what a lot of people recommend, I just find that you’re burned out by the one in the afternoon. And if the one in the morning runs late, then it becomes problematic.

Nisreene: Yeah. Do you ever trade off with your – or do you recommend that parents maybe trade off so that they can also get a little bit of alone time to do whatever they want to do? Like, for example, do you say, “Okay, this morning I’m going to take the kids and go do this so you can go and do whatever you want” and then you sort of flop? Do you recommend doing that just so that the parents can also get a little bit of relaxation as well?

Nevin: Totally. You know, we went to Mexico City a few years ago, and one day I wanted to go to Pujol – the high-end Michelin star tasting menu restaurant to do their taco omakase, which was going to take, like, three hours. So I went there and did that. No-one else in the family even had an interest in it. And my wife wanted to go to an exhibit of Björk memorabilia that looked super cool, that I would have loved to have gone to. But it was, like, that was going to be her thing. So she went off and did that, and our son and I did something together. I think it’s really… that can get over the hump for people, you know? Sometimes there’s just something that somebody in the family, one of the adults, wants to do that, just, nobody else has any interest in. You should just let them go do it and take care of the kid or kids while they’re gone.

Nisreene: Yeah. And I feel like people get really weird about doing things on their own while they’re on a family vacation. Like, they feel like it’s not something that they should do, because they have to – it’s like forced family time. But I don’t know. I think there’s just something really nice about getting a little bit of, doing whatever you want to do while you’re on vacation that people maybe don’t always focus on or appreciate.

Nevin: Absolutely. I think you’re right in the sense that people feel like, “This is our family time together, so it has to be all family, all the time.” But think about your normal life. That’s not the way normal life is. Like, people go off to work, people go off to school, people go off to do their extracurriculars, they take their jog in the evening, whatever. When you suddenly say, like “For the next seven to ten days or whatever it is, we’re all going to spend all this time all together,” that’s, that’s just weird and abnormal for people. People need their time on their own, and people have their own interests that are specific to them. Let them enjoy themselves.

Nisreene: Yeah. And I feel like, particularly around the holidays, people feel a lot of that pressure even more so – that they feel like they need to sort of be together all the time when, in fact, I feel like the holidays is when you should take a few moments just for yourself. Well, let me ask you this, Nevin. Are you always the planner or do you ever take a break from planning? And if you do, is it difficult for you to relinquish planning control?

Nevin: For my family, I am always the planner of trips. First of all, it’s what I do. Second of all, I have more flexibility in my schedule, you know, than my wife does. Third of all, I love it. And, you know, and my wife and son both trust me to put together trips that they’re generally going to love – you know, with their feedback, of course. When I travel, you know, in larger groups, or I have a group of three friends that I travel with every year, you know, we all pick a destination together, we all choose the accommodations together. But then, you know, with input from everybody, I end up doing a fair amount of planning. But I’m actually okay with letting it go, because it is a lot of work.

Nisreene: So what I try to do, I try to find the balance. I’m like, “Okay, well, I’m going to plan the big – some big pieces, but I’ll let other people plan other small elements that, if they don’t go right, then it’s not going to, like, totally ruin my trip.” So, like, for example, I absolutely would never let anybody book the lodging.

Nevin: (Laughs) Yeah.

Nisreene: Like, I would never.

Nevin: Yeah.

Nisreene: Because I don’t think they’re going to spend the hours that I would spend reading reviews, cross-referencing, like, looking at the locations and all the amenities and things like that. Are there any other tips that you can give for people to help – who are the core planner and it’s super-tough to let go, but, like, any tips that you can give them to help them alleviate just a little bit of the stress, or maybe delegate a little bit of that planning work?

Nevin: Well, what I like to do is – like, my rule in life is, “If you’re the cook, you don’t clean up.” And so if you plan the trip, you know, there’s going to be drudge work that happens on that trip. Delegate and give people stuff that you don’t want to do. And, you know, if they give you grief about it, just remind them how much work you did to get them there and how much work you’re doing as you’re there.

Nisreene: My one last question for you is, of all the experts that you’ve spoken to, of all the people that you’ve met on the ground, from your experience of traveling with family, what are some of the best tips that you can give people for booking a, you know, family vacation for the holidays that really sticks out to you most? Like, if people walk away with one or two tips, what do you want them to walk away with from this show?

Nevin: Don’t over-plan. Plan just enough so that there’s flexibility in your schedule and there’s time for people to just enjoy a place at their own pace and do what they want to do. Try to pick activities that are both within people’s comfort zones, but also pick a couple of activities that are slightly out of people’s comfort zones, that introduce them to new things, whether that’s new cuisines or new kind of adventure elements to a trip. Nothing too far out, but, you know, push people to get out of their comfort zones and really experience the place that you’re in, the people that you’re meeting, the things that you’re doing. The last piece of advice I would give is that every trip you take is really prep for the next trip you take as a family, so that if things go really bad because of you – you know, I am always thinking, like, “I want this trip to go well enough that we all want to go on a trip together again soon.” And just conduct yourself well in the world.

Nisreene: Yeah. No. Beautiful words to end by, honestly. Nevin, thank you so much for coming on the show today. It’s been an absolute pleasure and I feel pretty inspired to take my little threenager on a big trip. Maybe we’ll go to Mexico. Maybe we’ll go to Tulum. I like it. Thanks for coming.

Nevin: I hope that you guys go somewhere and have an amazing time.

[Musical interlude]

Nisreene: While I’m still a little jaded from all of the stress of planning my last big family vacation, this has really inspired me and armed me with all the tips to really think about potentially doing it maybe one more time. We’ll see.

Are you the holiday booker in your family? Tell us how you deal with all the stress. Tag @Expedia and @PRX.

For more info on episodes, guests, and to find travel inspiration, be sure to visit Out Travel The System’s blog at

I want to thank our listeners so much for joining us today and, of course, I want to thank our guest, Nevin Martell, for all of the great tips. If you have any questions, comments, thoughts or, better yet, travel suggestions, be sure to DM us. We are @Expedia on Instagram. And don’t forget to give the show a follow and subscribe on your favorite podcast player so that you don’t miss an episode as soon as it drops.

Out Travel The System is brought to you by Expedia, with special thanks to PRX and Sonic Union. I’m the Executive Producer and your host, Nisreene Atassi. Special thanks to the following:

Additional writing by Kimu Elolia.
Producer Rishika Sharma.
Associate Producers Syma Mohammed and Nathanael Taylor.
Production assistant is Alex Thiel and Carolina Garrigo.
Theme music and original composition by Kevin J Simon.
Music edit, sound design, and mix by Rob Ballingall, and music supervision by Justin Morris.
Executive Producer and Writer Halle Petro.
PRX Executive Producer Jocelyn Gonzalez.

Out Travel the System is recorded with Sonic Union in New York City.

Join us next week as we speak to Maria Perrett about travel immersion and how to ensure you are fully experiencing the culture and community of the destination that you’re in.

Till next time, this is your host, Nisreene Atassi, for Out Travel The System. Find us on Apple Podcasts or wherever you listen. Happy travels!