Multi-Generational Travel: What NOT to Do!

Planning a trip with multiple generations of your family? Before you book, listen to this essential episode! Travel advisors Ryan and Julie share hard-won wisdom about the most common mistakes families make when planning multi-gen vacations—and how to avoid them.

From the planning phase through your actual trip, they cover everything: why you need to nail down dates BEFORE contacting your travel advisor, the importance of having a "team leader" for your group, and why trying to do everything together is a recipe for stress (spoiler: those Disney families of 20 walking in a line aren't having as much fun as you think).

Discover why cruises and all-inclusives work so well for multi-gen groups, how to handle different budgets within the same family, and the critical conversation about who's paying for what. Julie shares real stories from her own family trips and client experiences, while Ryan offers practical tips about room configurations, meeting points, and making sure everyone's expectations are aligned.

The hosts emphasize that while planning some group activities is important, the magic often happens in the unplanned moments—cousins running to each other in the Magic Kingdom, spontaneous trivia sessions on the cruise ship, or simply sharing a meal together. They also tackle the delicate balance of ensuring the person treating the family doesn't have their preferences overlooked.

Whether you're planning a cruise, Disney vacation, or all-inclusive getaway with grandparents, siblings, and kids in tow, this episode will help you create a memorable trip that brings your family closer together—without the drama.

Transcript

j_1_10-31-2025_145008: 0:10

Hello and welcome to All Things Travel. One of our areas of expertise is multi-generational travel. type of travel has become really popular over the last few years as families are truly busier than ever, and a multi-gen trip is a great way for everyone to get away together and have some quality time without. Having to clean the house and do the dishes and all those kinds of things. So today we're gonna tell you about what not to do when you're planning your multi-gen trip and things to think about for during your trip.

ryan_2_10-31-2025_145008: 0:47

Listen in with travel advisors and destination experts. Ryan and Julie. I'm your travel professor teaching you everything you need to know to have a magical vacation, and she's a Disney loving Maryland mom of three and a specialist in family travel. Whether we're discussing incredible destinations, top vacation tips, or sharing personal stories, it's always all things travel. Julie, this is really your wheelhouse, isn't it? I've planned many multi-gen trips, but this is really your bread and butter.

j_1_10-31-2025_145008: 1:22

It's, and I kind of started with that because I was personally taking a lot of multi-generational trips with, my family in-laws extended family, nieces, nephews, things like that. So obviously I just learned a lot from that, that I can share with my clients and I feel like it lends a lot to my client base, to my niche, which is

ryan_2_10-31-2025_145008: 1:42

Yeah. Yeah.

j_1_10-31-2025_145008: 1:43

with young kids. There's always those grandparents that also want to go with them, or maybe a brother, sister, cousins. So there's a lot to think about with these trips we thought it would be a great idea to kind of run down things you need to know when you're thinking about this type of trip.

ryan_2_10-31-2025_145008: 1:57

I love it. Well, before we get into the list, I wanna remind folks if they did not listen to last week's episode. We talked all about Alaska shore excursions.

j_1_10-31-2025_145008: 2:08

so I wanna start with mistakes that you could make. While you're planning your trip, and I think the most there, there's two like very important ones here, and they're ironically at the top and the bottom of my list.

ryan_2_10-31-2025_145008: 2:20

Okay.

j_1_10-31-2025_145008: 2:20

everyone should sit down and plan your dates before contacting your travel advisor. if you're unsure, which season is best for your family or for your. Donation, at least have a few date ranges in mind. otherwise it feels like a little bit of a waste of time to be going around in circles. And then your sister's family says, oh, we can't do that week. when you come to us, we want to make sure everyone is on the page about when you're going.

ryan_2_10-31-2025_145008: 2:49

So the mistake is not knowing when people are available and not having that ironed out. Okay. I gotcha.

j_1_10-31-2025_145008: 2:55

because you could say, oh, we really wanna go at this time of year, and then you forget so and so has a baseball tournament, or this one is in the school play. Or, you know, mom and dad can't go during this time. just have your dates ready to go.

ryan_2_10-31-2025_145008: 3:09

Got it.

j_1_10-31-2025_145008: 3:09

like when multi-generational groups have a group leader. someone that I can contact easily, but I also want everyone to be available on a phone call, or on our zoom meeting,

ryan_2_10-31-2025_145008: 3:25

Yep.

j_1_10-31-2025_145008: 3:25

it is, because that way I know that everyone is on the same page. It's challenging sometimes to plan a troop when sometimes you have that part of your family that's like, I don't care. Just tell me what to do and where to go. And then you start planning and then they realize

ryan_2_10-31-2025_145008: 3:40

And at, at, at the 11th hour, they swoop in and you're like, I have not talked to this person at all. And now they're changing things up. Yep. I've been there, done that. even with a friends group, you know, I'm thinking of a recent river cruise. with four friends. there was one person who I had worked with before, and that kind of turned into the team leader because I had a rapport with her more than the other women. another thing you wanna make sure you do in the planning phase is make sure that everybody is in agreement with at least the destination, the main activities that everybody's going to do, and also a general price range. Now, I will say as a travel advisor, we can offer differences, so some people can stay in a garden view room versus others who want to stay in an ocean view room. Or we can have some people go on a more extended activity and other people don't. So we can within the group, change those things. But you need to have some of those key larger group things nailed down.

j_1_10-31-2025_145008: 4:43

And what this reminds me of is a lot of times I'll have a multi-gen group come to me and say, we all wanna go on this cruise next summer. And so we start researching cruises. And then they come back, okay, well nevermind. My sister is very much against a cruise.

ryan_2_10-31-2025_145008: 5:01

Right,

j_1_10-31-2025_145008: 5:02

well where are we going then? I have that happen More often than I'd like. Try to choose a destination that offers something for everyone and something that they can do on their own time. cruises and all inclusives really play into this because at an all inclusive, if so and so wants to go sit on the beach all day, great. The other family can go to the pool all day. You don't have to be side by side all day. similar to a cruise, you could be doing activities on board, you could choose different excursions at a port. Disney can be a little bit tricky with this, but I have created multiple touring plans for the same family or written into one touring plan. little kids can do this ride while

ryan_2_10-31-2025_145008: 5:45

Right.

j_1_10-31-2025_145008: 5:46

go do this. Something like that is really doable. or maybe the grandparents wanna take a break that day. it's doable. It just takes a little bit more thinking, We mentioned this briefly, but choose a destination that also offers different price points. Ryan mentioned choosing that garden view room versus an ocean view, or different excursions. This is why I love a cruise for multi-gen, because you could be in an inside cabin and ocean view, a balcony, concierge. There's so many different options to truly fit everyone's needs. can do that similarly with all inclusive, and

ryan_2_10-31-2025_145008: 6:23

Yeah.

j_1_10-31-2025_145008: 6:24

you can do that similar with Disney, but a lot of times what ends up happening with Disney is you may end up at different resorts. so I tend to say let's pick a moderate level price range that everyone's in agreement with for Disney as opposed to forcing everyone to go higher or lower. and along with that, you may not to book that three bedroom. Villa or apartment that everyone can fit into. You might want to have own spaces

ryan_2_10-31-2025_145008: 6:53

some space. Yeah. A lot of people come to us and they say, we want to have a place where everybody can be together, and that's great and there's certainly options for that, but also having distinct places for each family Doesn't really hurt, especially if it's a longer trip. think of number of bathrooms, quieter spots for people that want to take naps, whether it be kids or adults. being on top of each other on a trip like this is not necessarily always the most fun. maybe grandma and grandpa have a larger room and that becomes the clubhouse, And then at the end of the day, everybody leaves and they have their own space.

j_1_10-31-2025_145008: 7:29

I've done trips like that before where grandma and grandpa have like a villa and everyone can congregate in that common space. Or I've also done it where, multiple families are in a club level location. the club level lounge kind of becomes their communal

ryan_2_10-31-2025_145008: 7:44

Yeah. Yeah.

j_1_10-31-2025_145008: 7:45

not private obviously, but still a great place for gathering.

ryan_2_10-31-2025_145008: 7:49

Julie, along with having that team leader, one of the things that is really important and your team leader can help you with is getting everybody's contact information. What's the information that you are going to need to make the bookings to change things around if needed? if the travel advisor's helping you with flights, do you need to know the known traveler numbers or their frequent fire numbers? You know, all this kind of stuff. even if you're not working with a travel advisor. It's important for a person to have all of that because they may be calling the hotel on your family's behalf.

j_1_10-31-2025_145008: 8:25

Yes. And it's hard to be like, well, it's so-and-so's sister, but I don't actually know their email

ryan_2_10-31-2025_145008: 8:31

Yeah.

j_1_10-31-2025_145008: 8:31

that.

ryan_2_10-31-2025_145008: 8:32

Yep, absolutely.

j_1_10-31-2025_145008: 8:34

the next one is, Really important. Decide who is paying for what in advance. Sometimes this looks like grandma and grandpa are paying for everything, but when they say everything, do they also mean meals? Do they also mean flights? Do they also mean transportation or they truly mean or the cruise itself? you could also divvy this up as far as. Things like, so-and-so is paying for transfers and this person's paying for an excursion. we need to know, and you need to know in advance who is paying for what. So there's no confusion on that. I also wanna say to plan to arrive together, and this is more for ease of transportation. You know, it doesn't make sense if you're all arriving on the same day to have flights coming in at very different times. It's just easier to just do one transportation. And the very last one for this is to make sure you have expectations set in advance. This can just avoid a lot of arguments. that this family has must dos and the other family has must dos, and it's okay if those are different. Must dos.

ryan_2_10-31-2025_145008: 9:45

and it really is hard for us sometimes when we see, one person is really treating their family to a trip

j_1_10-31-2025_145008: 9:52

Mm-hmm.

ryan_2_10-31-2025_145008: 9:53

their expectations are the last ones to be considered. it is sometimes balancing priorities within a group and, and not often, but, you know, there's been some interesting conversations when it comes to planning these types of trips.

j_1_10-31-2025_145008: 10:07

Always.

ryan_2_10-31-2025_145008: 10:08

Julie has a lot more suggestions for during your travel, but first she's gonna talk about a cruise when it comes to where in the world is Wonder and Beyond Travel.

j_1_10-31-2025_145008: 10:20

Yeah. And this one is exciting because it's a personal cruise and

ryan_2_10-31-2025_145008: 10:24

Nice.

j_1_10-31-2025_145008: 10:25

soon. I'm pretty sure by the time this episode comes out, I will be back and I can't wait to talk about it later. this is exciting because it's a seminar at sea, so that means that we were invited to go to some training with Royal Caribbean, and that training just happens to be on a cruise ship in the Caribbean. I will be doing a four night cruise on the Wonder of the Seas, which is in oas. This class ship similar to Utopia of the Seas that we were just on, but a little bit different. my husband is coming with me. We have a Ocean View balcony room, which was assigned to us. I was very pleasantly surprised. we have a couple days of training, we go to Nassau, but I believe the day we're at Nassau, we have a, a morning of meetings and trainings and, and meeting with Royal Caribbean. so I'm excited for that. Our day at sea, we're in meetings a lot of the day, but we also get to try some of the specialty restaurants throughout the day, so

ryan_2_10-31-2025_145008: 11:18

Awesome.

j_1_10-31-2025_145008: 11:19

for that. and then of course we have Perfect Day Coco K, we are getting a tour of the island. And then I have booked us for Hideaway Beach. I wasn't gonna do that'cause I just wasn't sure if I wanted to spend the extra and you know, would we have time? But then I kind of thought, when else are we going to be going on a careers without children that

ryan_2_10-31-2025_145008: 11:42

Yeah.

j_1_10-31-2025_145008: 11:42

to Hideaway Beach?

ryan_2_10-31-2025_145008: 11:44

even if you just go for a couple hours after you're done with your stuff, I still think it's worth the price.

j_1_10-31-2025_145008: 11:49

yeah, absolutely. Steven's not going on the tour, so he can go hang out at Hideaway Beach

ryan_2_10-31-2025_145008: 11:53

Yeah.

j_1_10-31-2025_145008: 11:54

I will be working a lot on that trip. So Steven is also planning on working a lot on that trip, and that's how we're, justifying this one.

ryan_2_10-31-2025_145008: 12:01

Okay. we will be anxiously awaiting to hear how much work you and Steven actually get done on your adults only crews

j_1_10-31-2025_145008: 12:09

I'm excited.

ryan_2_10-31-2025_145008: 12:10

we love learning about where our clients are traveling, even when we're the clients. That's part of the fun, and we also love to highlight them on the podcast. So who knows? Maybe if you work with Wonder Beyond Travel, your trip will be featured next. All right, Julie, we are doing the trip. We've done the planning. The number one thing is, like you said, set the expectations. and I say this every time I work with a multi-generational trip, do not try to do everything together. If you're the Disney family of 20 walking down the sidewalk, or if you think everybody needs to pick out their pool chair by 7 45 in the morning, you're gonna be. Really stressed out and disappointed by the end of the trip.

j_1_10-31-2025_145008: 13:01

Yeah, that sounds exhausting. And, you know, it sounds so tempting to, have one big plan and we're all gonna do this and it just doesn't end up working out. What I've found in larger groups, especially at a place like Disney, is you spend half the time waiting for people to go to the bathroom. As silly as that sounds

ryan_2_10-31-2025_145008: 13:22

Oh, it doesn't sound silly at all. Yeah.

j_1_10-31-2025_145008: 13:24

and it's like, oh, so and so has to go. We're gonna stop and so and so's gonna go. You don't have to go,

ryan_2_10-31-2025_145008: 13:28

Yeah.

j_1_10-31-2025_145008: 13:29

now we're gonna walk. And then it's like, oh, now I have to go, or now the baby needs to go, So just setting the expectations that it's okay that you're gonna do this and I'm gonna do this and we'll meet up later.

ryan_2_10-31-2025_145008: 13:39

sometimes it's people doing stuff separately during the day and then meeting up for dinner. Sometimes it's setting an evening where, the young adults can go out and grandma and grandpa watch the kids. or maybe it's a time where grandma and grandpa get to go out and have a date. one of the first times I took my parents to Disney, my dad actually found out through social media. That one of his high school friends was staying across the lake at another resort and he went over and talked to him, this family goes to Disney all the time. What the grandparents do is they spend one day with each family. So Wednesday they spend the day with your family, and then they spend the day with the next family, and then they have a day off. they're rotating around. They're not feeling like they have to be with everybody all the time. I kind of like that idea.

j_1_10-31-2025_145008: 14:24

That's so interesting. I haven't thought about doing it that way. I'll also mention, if you are traveling with multiple rooms, we can put a request in for those rooms to be near each other or connecting, but it is not guaranteed. which could be a pro or a con depending on your family.

ryan_2_10-31-2025_145008: 14:41

Absolutely. one of the things to consider is maybe there's meeting points, throughout the resort. So maybe, you know, hey, we know that we always meet for dinner in the lobby, or we always know we meet at the pool, in this spot. this is the. Exit to the, to the resort that we always leave from that can really help folks. obviously, this has changed a lot with apps for the resort that maybe has messaging the same with cruises, being able to message with the wifi at the resort or on the cruise so people are in much more contact. planning some of those things ahead of time, really helps out. I will say with all of this As much as we're saying, don't try to be together all the time. Do plan at least a couple times where everybody's together. This is the time to get your pictures. This is the time to have a meal and say thank you to the person that maybe has paid for the trip. have a couple times where you are connecting as a larger group and take those pictures and have that fun.

j_1_10-31-2025_145008: 15:44

so the last big thing I don't want you to make the mistake of is don't miss the little moments. It's really fun to plan the big moments, to plan the big excursions, to plan a fancy meal or to plan the big character meal, or that we're all gonna go on this ride together. But a lot of times those little moments are. cousins running up to each other when they first see each other in the Magic Kingdom. going off and doing the water slides together at your resort, going to a trivia session or a silent disco on your cruise ship. Things like that, that happen much more spontaneously that you can't really plan. I struggle with this, traveling with my family and I know many families do. feel like you're on a schedule to get and do the things that you've planned in advance, and you don't wanna miss anything. But please make sure you slow down, especially with a larger group, and enjoy those little moments, seeing all the little kids watching the fireworks together. all the adults being together in one space, sharing a meal, things that don't happen in your everyday life.

ryan_2_10-31-2025_145008: 16:55

I really love that. I think that's the perfect, cherry on the top with our discussion today when it comes to multi-gen travel. And the last bit of advice that I would have is if you haven't done it and you like your family, try it. It's a lot of fun. But notice I said if you like your family, the world is full of wonder Your next adventure is waiting at Wonder and Beyond Travel. We work with you to create a one of a kind journey, taking the stress off your plate so you can focus on the joy of exploring and the memories that will stay with you forever. If you're ready to start planning or you just want to dream a little bigger, head on over to Wonder and beyond travel.com, and we would love to help you get started. We look forward to talking to you next week on all Things Travel, when we discuss one country, three budgets in Japan.