Making Multi-Generational Travel Work for Everyone

Multi-generational travel tips for planning successful family reunion vacations with grandparents, grandchildren, and everyone in between. Learn destination selection strategies, hotel vs. vacation rental pros/cons, activity planning for different ages and abilities, navigating money conversations, and managing group dynamics on trips spanning toddlers to seniors.

Episode Highlights:

• Choosing destinations that work for all ages and mobility levels
• Travel agent vs. DIY booking for large groups
• Hotel vs vacation rental decision-making for 6+ people
• Splitting activities by interest while staying connected as a family
• Handling the money conversation before booking
• Managing dietary restrictions and mobility needs
• Real examples from Hawaii, Caribbean cruises, and more

00:00 Welcome to Family Travel Unpacked

01:19 Choosing the Perfect Destination

04:54 Planning the Trip: Travel Agents vs. DIY

08:03 Booking Early and Getting Commitments

10:50 Hotel vs. Vacation Rental: Making the Right Choice

15:19 Flexibility in Activities and Logistics

19:31 Navigating the Money Conversations

23:30 Managing Interpersonal Dynamics

28:01 Final Tips for Multi-Generational Travel

Hosted by Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

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Transcript

  📍  Hey there and welcome back to Family Travel Unpacked. I'm your host, Melissa, and in case you're new here, welcome. You can always check out my detailed destination guides, travel tips, hacks, and more on my website, thefamilyvoyage.com.

Today we're talking about something that can be amazing or completely stressful, but usually both in the same trip, and that's multi-generational travel. I'm talking about trips that include everyone from toddlers to seniors, multiple family units, different travel styles, and all the logistics that come with coordinating a big group.

We've done quite a few of these trips over the years: Hawaii twice, we've done an all-inclusive resort in Cancun, a mountain cabin getaway, weekend city trips, and we're about to take our second Caribbean cruise with a huge group ranging from preschool up to a senior citizen.

And let me tell you, as the primary planner, I've learned a lot along the way. Some things, the easy way. Ah, some things not so much. So whether you're planning your first major family reunion trip, or you're a veteran of multi-gen travel, looking for fresh ideas, I'm gonna walk you through the whole process we use.

I'll talk about how to choose a destination that works for everyone. The nitty gritty of planning, logistics, whether or not to use a travel agent, the hotel versus vacation rental debate, how to balance activities when different people want different things, and probably the trickiest part, navigating the money conversations.

Let's dive in.

First things first. How do you even pick a destination when you're trying to make sure everyone's happy? Because here's the thing, what works for a couple looking for adventure is completely different than what works when you're traveling with a 2-year-old, a teenager, and a grandma who moves slowly.

We're actually in the middle of picking our family's next destination right now for us, the timing usually dictates a lot of the decision, and that's the first thing you need to pin down.

Multi-generational trips often happen during school breaks, particularly winter break for our family, because that's when everyone's schedules can actually align between sleepaway camp, theater productions, band concerts, and soccer tournaments. Coordinating even our immediate family is a challenge the rest of the year.

Add in other families with their own work schedules and commitments with their own work schedules and kid commitments. Winter break is the obvious choice for us. And when you're locked into late December or early January, and most of us are coming from the Midwest where it's freezing, that kind of narrows things down. We are not looking at European city breaks. We're looking at warm weather destinations. The Caribbean and Hawaii are a natural fit, but beyond just somewhere warm, you need to think about what different people in your group actually need. Not just want, but need to have a good trip. For example.

For example, you might have somebody in your group who has a hard time with stairs, so destinations that require a ton of walking or have accommodations spread across different levels, that's out. Then you've got dietary restrictions. My daughter and her cousin both have celiac disease, which means we need to go places where they can actually eat. Costa Rica is amazing. Japan, that'd be a really challenging for them 'cause gluten hides in everything, cruises usually do a good job, and that's part of why we have one coming up this year. All inclusives can be hit or miss for allergies and food sensitivities so you really have to do your research.

When it's just our immediate family, we can navigate those trickier food situations pretty easily. But with a big group, it's important to minimize the stress. You also need to think about the range of activity levels in your group. Some people want adventure and excursions every day- that's me. Others, and this is totally valid, they just need to sit by the pool with a good book during their vacation.

The destination needs to accommodate both if there's a split in your group. That's actually one reason Cruises work well for us and other big family groups. On a cruise if some people wanna go zip lining in port and others just wanna stay on the ship and relax, everyone can do their own thing. You're not negotiating over one rental car or trying to coordinate a bunch of different taxis unless you want to.

If some family members are already really well traveled, they might say they don't wanna go back to a place they've already been. That's totally valid, but with so many other constraints in play, it might not be the top priority that I would focus on personally.

Another factor you might want to consider, and I talk a lot about this on the podcast, is points and miles. When you're booking for a large group, those costs add up fast. Sometimes it makes my eyes water when I see how much it is for 13 people to go on vacation together. If everyone's paying their own way, being able to use points strategically can make a trip financially feasible that otherwise wouldn't be at all. Instead of setting a firm budget, you could look at where you can all maximize award availability to keep costs like flights and hotels in check.

So to sum up destination selection, start with your constraints. When can everyone travel? What's the weather like? Then what are the physical limitations, if any? What are your group's dietary needs? And then look at destinations that accommodate different activity levels and interests. If you can, factor in where you can leverage points to make it more affordable for everyone.

Okay, so you've picked your destination and now comes the fun part, actually planning the trip. But this is where things can also get complicated fast. First, let's talk about the travel agent question because it does come up a lot. Should you use one for a multi-gen trip or book everything yourself?

Personally, I've done it both ways. I booked our Hawaii trips myself because I was able to get excellent small business rates at the hotels we wanted, and I'm really familiar with the destination since we've been there so many times.

But I used a travel agent for both of our cruises and for our Cancun, all inclusive. I really needed help to narrow down our options and try to get better rates there. Here's what I've learned.

A travel agent can be really valuable for multigenerational trips, for a few reasons. First, they can serve as a buffer for challenging family dynamics. Instead of being in the middle of "Aunt Susan wants an ocean view room, and Uncle Bob thinks it's a waste of money", the travel agent can present the options and handle those hard conversations.

Second, they can help you weed through overwhelming choices. There are literally dozens of all-inclusive resorts near Cancun. There could be at least five or six cruises that work for your exact dates and the departure port that you want. A good travel agent knows the properties, knows which ones are better for families, what has a more accessible layout, and which ones have better food options for picky eaters. That knowledge is invaluable when you're trying to make everyone happy.

For cruises specifically, travel agents can sometimes get you better deals or onboard credit. They can also advise on state room locations. Like if you have someone who might get seasick- that's my sister-in-law by the way, you wanna put them midship on a lower deck to keep them comfortable. If somebody's got a bad knee, being near the elevator can be really helpful, but the travel agent can make sure it's on the right deck and not just below the nightclub. Those details matter.

And there are plenty of great travel agents that don't charge you anything. They just get a commission from the, they just get a commission from the cruise ship or the resort for your booking.

The other nice thing about using a travel agent is that if something goes wrong, they can usually help you resolve it. But that's a double-edged sword, and to me, it's the biggest downside of using a travel agent if something goes wrong. You can't usually deal personally with the resort or cruise line directly.

When the massive southwest outage happened, a few winters ago, our family's flight to Mexico got canceled and I couldn't talk to the resort myself. Everything had to go through the travel agent, and that added a layer of complexity and sometimes delay. Lots of resorts and cruise lines have dedicated travel agent divisions, and they won't  bypass that system even in an emergency.

That might be great if you'd rather be hands off in that kind of situation, but I'm used to doing all the legwork myself, and I like talking directly with airlines and hotels so that I can resolve issues as quickly as possible. There might be questions or ideas that come up in conversations that you hadn't thought of when you were having a separate conversation or email chain with your travel agent, and then they're the ones talking to the company.

So my take is this, for a straightforward trip where you know exactly what you want to do and you're comfortable researching the options, just book it yourself. For more complex trips with lots of variables. Or if you're not sure which specific properties or cruises will work best for your group, a travel agent can be worth their commission.

Now, regardless of whether you use a travel agent or not, you need to book early for multi-gen trips- way earlier than you might just for your immediate family.

First, if you're traveling on points, getting award availability for a large group is extremely challenging. Airlines release award seats 11 or 12 months in advance, and if you want to use points for eight to 10 people or maybe more, you need to be searching the day those seats become available.

Second, good accommodations for large groups book up fast, especially during peak travel times like winter break. If you wanna do a vacation rental, there are only so many options that can fit a huge family. Even at a hotel, if it's important to you that all the rooms be equivalent, so there aren't any hard feelings, you've gotta line those up pretty far in advance. And third, this one's crucial, you need to give people time to commit. Getting everyone on the same page about dates, having PTO approved, getting them to actually book their flights, making sure they understand deposit deadlines, that all takes time. And the more people you're coordinating, the more time it takes.

Which brings me to one of the most frustrating aspects of multi-generational trip planning, getting people to commit and follow through. On one of our trips, one branch of the family kept going back and forth on who exactly was coming and what activities they wanted to do. They finally booked their flights just two weeks before the trip. By that point, the hotel cancellation deadline had already passed, and since I booked everything on my credit card, I was on the hook if they changed their minds.

While they ended up coming, it was really stressful and taught me an important lesson: you need to set clear deadlines and expectations upfront. If there's a cancellation deadline for the hotel, everyone needs to have their flights booked well before that. If people can't commit by a certain date, they might need to sit this trip out. I know that sounds harsh, but when you're coordinating a big group trip, you can't be in limbo. Other people's indecision can have real financial consequences for whoever's doing the booking.

And you know what? Putting those timelines front and center works. For our upcoming cruise, someone backed out just a few days before the cancellation deadline. Cruises are a lot less flexible than hotels, so there were some tense conversations. Fortunately, our travel agent had our back, and she was the one working with the cruise line to understand all of our options. Thankfully, we all had our eyes on that date, so we knew when final decisions absolutely had to be made, and we were only out $250 instead of a lot more.

The other logistical reality that changes with group size is transportation. When we went to Hawaii with six people, that was my immediate family and two grandmas, we rented one minivan and did pretty much everything together. We were small and nimble.  With 13 people, we needed three cars. That meant we couldn't always move as one unit.

also If we wanted to go out to dinner, we had to make reservations well in advance or send someone ahead to put our name on the wait list because restaurants don't just have tables for 13 ready to go. These aren't huge problems, but they require a lot more thought.

Speaking of Hawaii, let me tell you about two very different Hawaii trips. The first time we went on a multi-gen trip to Hawaii, as I said, there were six of us and we stayed in a vacation rental.

It was perfect. We had a big kitchen, multiple bedrooms, a living room where we could all hang out together, and a great lanai where we could watch rainbows over Kaneohe Bay. We packed that house with groceries and made breakfast every morning. We'd come back from the beach, someone would throw lunch together, and it felt like a real home base. The second time with 13 people, we stayed at a hotel and paid for four rooms. Yikes. But it was absolutely the right call.

Let's talk about this decision because it's a big one for multi-generational trips, hotel or vacation rental. Vacation rentals have some real advantages. The biggest one is space. Everyone can spread out. The teenagers can hang out in one room, the little kids can play in another, and the adults can have conversations without whispering while the kids are asleep.

The second big advantage is the kitchen. If you're a large group, eating out every single meal gets so expensive, and it's also exhausting if there are kids in play because somebody might need an early dinner, somebody's impatient, it's tough. Being able to make breakfast pack lunches for beach days or throw together simple dinners some nights saves a lot of money and stress.

There's also something nice about bonding time that happens in a vacation rental. You're hanging out over coffee in the morning, somebody's chopping vegetables for dinner while the other one's telling a story about their day, and you get the little cousin playing on the floor while the adults chat. It feels more like real life, but in a nicer setting.

But this is important. Vacation rentals have downsides that get bigger as your group grows. First, most vacation rentals just aren't big enough for 13 people, 16, 20, however many you have, and the ones that are often have long minimum stays during holiday weeks. We would've been locked into more days than we wanted in Hawaii if we'd tried to go with a vacation rental. Over winter break, some of them require a two week stay, and that just can't happen for us. Some of the other ones might have short stay requirements, but those get booked up super early or they might not have enough capacity for your family.

Second, and I'm gonna say this really honestly, when you have that many people, personality clashes are inevitable.

Somebody's idea of clean is different from another person's. One person thinks the dishes should be done right away. Another person thinks they can wait until morning or maybe be done by the dish fairy. Someone's offended that the others aren't helping to cook, while those people think they're on vacation and they shouldn't have to.

In a hotel, housekeeping comes every day. You probably have each household in their own room. So there's no issue with different expectations. Nobody's fighting over who's turn it is to do the dishes. Different ideas of cleanliness don't matter because the staff is handling everything and you all have your own space, plus you're probably eating out, so there's no argument about food.

The third issue with vacation rentals for big groups is coordination. Who's buying the groceries? Who's cooking? What if some people are vegetarian and others want meat at every meal? What if someone has celiac disease like my daughter, and you need separate cooking surfaces and utensils? It can get complicated.

Now there are ways to make vacation rentals work really well for big groups. You could hire a chef to come in and cook some of the meals. That's really popular on smaller Caribbean islands. You could also designate specific people for different tasks, so it's not ad hoc. You can set clear expectations ahead of time about cleanliness and sharing responsibilities.

But for us, with 13 people representing different family units and different standards and expectations, the hotel was the path of least resistance. Everyone had their own space. We could all choose what to eat without negotiating with 12 other people, and nobody was passive aggressive about bathroom scheduling or whose kids left toys everywhere.

Here's my rule of thumb. Up to, let's say six or seven people, especially if it's mostly one immediate family, plus a grandparent or two, a vacation rental can be wonderful. Heck, we could even do it with up to about 10 people if it's a big enough place. You get space, the kitchen, the bonding time, and the cost savings without too much interpersonal friction.

Beyond that size, or if you're combining a bunch of different family units that don't live together normally a hotel is easier. Yes, you'll spend more on food, but you'll save your sanity and probably your family relationships too.

The one exception might be if you're going somewhere remote, where hotels really aren't an option, like a mountain cabin or a lake house. We did a cabin in the mountains when the kids were little and it was great, but that was a weekend getaway. Everyone drove so we could bring tons of food with us, and by the time we were getting annoyed and tripping over each other, it was time to go home anyway. For a week long trip in a more traditional vacation destination, I'd probably lean hotel for a group that size.

Now, here's something people don't usually talk about with multi-generational travel. You are probably not going to do everything together, and that's okay. In fact, it's more than okay- it's often really important. When it's just your immediate family, you can push everyone a little bit. Your teenager might not be thrilled about the museum, but they'll go. Your younger kid might find the hike challenging, but you'll encourage them and they'll make it to the top. You're working with a smaller group that knows each other's limits and can negotiate them.

With a multi-generational group, you've got a much wider range of abilities, interests, and frankly, willingness to compromise. Our family's bookends are four and 78, with a lot of different ages in between, and that really has an impact on how we structure our trips.

Let me give you some specific examples from our recent visits in Maui. I booked a kayaking and snorkeling excursion for 10 of us. It was several hours on the water, physical activities, definitely an adventure. The other three people in our family opted out and drove the road to Hana. Instead, they wanted to see the scenery and weren't as interested in the water activities, and that was perfect. Everyone got to do something they actually wanted to do.

In Cancun when it was just our immediate family and my mother-in-law at the end of the trip, the four of us went caving at Rio Secreto and that is not a casual activity. You're underground in the water, there's climbing, it's adventurous, it's kind of intense. We're talking wetsuit, life jacket and headlamp. There was no way my mother-in-law could do that and she wouldn't have wanted to anyway, so we sent her to a spa day instead. She had a great time. We had an adventure and we all met up happy later.

The key is building in the flexibility from the start. Don't plan every single moment as a group activity and then feel disappointed or frustrated when people want to split up.

Instead, pick the moments that are really important to have everyone together. Maybe it's dinner every night or maybe it's breakfast for your family, and leave the rest flexible.

That said, you do need to think about logistics if you're going to split up. On Maui coordinating two different activities meant two different groups needed transportation. We had to plan ahead for that and make sure we had enough seats in each car.

In Cancun, when we booked offsite excursions for our big group, we needed to charter a large enough van for everyone, and in one case, I even had to charter a second snorkel boat.

These things don't just happen spontaneously. Someone, usually me, is working hard behind the scenes to pull it all together.

For our upcoming cruise, the nice thing is that the main logistics are already built in. Everyone's sleeping in the same place, dinner brings us all back together naturally, and during the day we can go our separate ways without complicated transportation if we need to.

There's also something to be said for what I call parallel play when everyone's in the same location but not necessarily doing the same thing. At the pool some people are swimming, while others are reading on a deck chair. At the beach. Kids are building sand castles, i'm out snorkeling and my teenage niece is napping under an umbrella. You're together, but not forcing identical activities on everyone.

Part of the reason we loved our time in Maui is that we were smart and stayed at the Andaz Wailea. It's the perfect kind of hotel for groups with some relaxers and some people who want to stay busy because there's a fully serviced beach and tons of pool deck space. Plus they include kayaking, outrigger canoe excursions, snorkel gear, and all sorts of other activities in the resort fee, which is waved on points by the way, and there's great snorkeling right off shore. I could stay super busy doing all these amazing activities without driving offsite or spending any extra money.

And that parallel play I was talking about works really well for multi-gen groups because proximity creates connection. The thing to avoid is having rigid expectations about togetherness that can end up creating resentment. If someone's forced to do an activity they don't wanna do, they're probably gonna be grumpy about it and that affects the vibe of the whole group. It is much better to say, Hey, we'll do this one together, but the other one's optional and we'll meet up later.

And look the dynamics of who wants to do what can be complicated. Sometimes a teenager doesn't wanna hang out with their younger cousins. Sometimes people have different ideas about how much food to order, and every car ride can feel like a game of musical chairs because people might wanna ride with relatives they don't see all the time, or with the ones they're closest to.

These interpersonal things are real and they're magnified when you're all traveling together. The more people you add to a trip, the more these dynamics come into play. You can't eliminate them, but you can minimize friction by building in flexibility and not expecting everyone to move as one unit every moment of the day.

It's time to talk about probably the trickiest part of multi-generational travel: money. Nobody really wants to have these conversations, but if you don't address it upfront, it can cause problems later. I've seen it happen and I've heard from enough readers and listeners to know that this is where things go sideways .

 Let's talk about the different ways families handle costs on multi-generational trips. There's no wrong way. The first model is splitting everything equally. If you're three couples on the trip, you split the vacation rental costs three ways, or everybody pays for their own hotel room. You split the rental car three ways. When you go out to dinner, you split the check three ways. It's simple and straightforward.

The problem is that it's not always equitable. If one couple has three kids and another couple has one kid, is it fair to split exactly equally? The family with three kids is using up more space in the rental, eating more food and taking more seats in the rental car. The family with one kid might say, we needed a vacation rental big enough for everyone, so we're paying for space that we don't need for your kids. See? Complicated.

The second model is each family unit pays for their exact share. So you divide the vacation rental costs by square footage or bedrooms, itemize the groceries, and everyone pays for what their family ate. When you go out to dinner, you each get a separate check or carefully split based on what you all ordered.

This feels fair in some ways, but it's also exhausting. Do you really want to be tracking who ate how many eggs from the shared grocery haul? Do you wanna be doing math at dinner while you're supposed to be relaxing and enjoying family time?

The third model is that one person or couple treats for the trip. In some families, the grandparents do this as a gift. It's their way of creating memories with grandchildren and bringing everyone together. In other families maybe one sibling is more comfortable and offers to cover the accommodation so that everyone can come.

Of course, when someone is treating, it's important to be gracious and not take advantage. If a family member is covering the accommodations, maybe you offer to pick up a few extra meals or get your airfare on points. Be thoughtful about what treating covers and what it doesn't. Regardless of which model you use, the important thing is to have those conversations before anyone books anything.

If you're splitting costs, you all need to know upfront what the expected per family cost is. If someone thinks they're splitting a $3,000 rental three ways and it turns out to be $6,000, that's a huge problem. If one person is treating, everyone needs to know what's covered and what's not so there aren't any awkward surprises. These conversations are uncomfortable, but they're really necessary. And honestly, the bigger the group, the more important they are.

One thing that can help offset costs for everyone is being strategic about flights. If you're using points and miles, that's one less expense to negotiate. Even if you're booking with cash, booking early and being flexible about departure times can save money. That makes the trip more accessible for everyone regardless of their budget.

This is also a great opportunity to get everyone involved with points and miles. If there are six adults going and you each open a Chase Sapphire Preferred, which I'll link to down in the show notes, that gives you 150,000 points per couple. That's basically enough for a week at some of the dreams all inclusive properties, and then you just have to call and add the kids for maybe a hundred bucks per night in cash.

Throw in some Southwest companion passes to fly the kids for free, and all of a sudden you've made the money conversation a whole lot easier.

You also want to think about activities. If everyone's expected to do the group excursions, are those included in the budget you've talked about? Or are they optional extras that each family pays for only if they want to participate? On our Hawaii trip, the kayaking and snorkeling excursion was optional. People could join if they wanted, but it wasn't included in the base cost While we decided that the whole family should go to a lu out together, and that was included in the budget.

I think the worst thing you can do is avoid the money conversation because it feels awkward, and then have someone feel resentful or stressed out about costs during the trip. That poisons the whole experience. So before you book, have the conversation, decide on the model and get everyone's agreement. And then if somebody can't commit financially, it's better to know that before the cancellation deadline rather than after.

Let's be real and talk about the relationship part of multi-generational travel. The more people you add to a trip, the more interpersonal dynamics you're managing, and sometimes those dynamics are challenging. I've touched on some of this already, but I wanna pull it all together because this is the stuff that can make or break your multi-generational trip.

First, there are dietary restrictions, and these can be easy or complicated, depending on your family. In our immediate family, we don't eat pork or shellfish. My daughter and her cousin have celiac disease. Someone else is trying to avoid dairy. If it's just your immediate family, you know everyone's restrictions and you can navigate them pretty automatically.

You know which restaurants work, you know how to read the labels and what questions to ask. With a bigger group, you're coordinating different sets of restrictions, and not everyone fully understands other people's needs. You have to communicate clearly and plan ahead. For restaurants that might mean calling in advance to make sure they can accommodate food allergies or choosing restaurants that have options that'll meet a lot of different needs. For grocery shopping if you're in a vacation rental, you've gotta be really clear about what everyone can and can't eat, and sometimes you'll have to buy separate items.

We've done a family card on Instacart, and this was, and it was perfect for that. Basically every Chase credit card that charges an annual fee gets Instacart Plus as well as a monthly credit. So be sure to use those benefits to make this even cheaper.

There's also the mobility and accessibility piece. Like I said, grandma moves pretty slowly now and she has a tough time with stairs, so we have to think a lot about accommodations that are accessible, activities that don't require a ton of walking,  and building in extra time for everything because we're moving at her pace.

If somebody in your group has those kinds of mobility limitations, it really affects the whole group, and that's okay. It's part of multi-generational travel, but you have to plan for it. Sometimes I'm guilty of not allowing enough transition time and then rushing because I'm used to traveling with just the four of us. Call it an area for improvement.

One thing that works really well if you have mobility challenges is the vertical layout of cruise ships versus the horizontal layout of resorts. I know that sounds counterintuitive. Wouldn't stairs on the ship be a problem? But cruise ships have plenty of elevators everywhere and things are relatively close by. At a sprawling resort, you might have a long walk from your room to the restaurant, from the restaurant to the pool, and from the pool back to your room. For someone with limited mobility, that gets exhausting and you're stuck waiting for a golf cart all the time if it's a huge property. We actually nixed our plans to take a big multi-gen trip to one resort that I love because we just felt like it was gonna be too difficult for grandma.

On a cruise you're never more than a short elevator ride away from anything, and you can choose your cabin location in advance to be close to the things that are priorities for you.

The other dynamics that come up are about different travel styles and expectations. Some people in your group might want to lounge by the pool all day. Others like me would go absolutely crazy doing that. You've got early risers who wanna maximize every minute, and you've got people who wanna sleep in 'cause they're on vacation.

Some of you might want every meal to be a perfect insta worthy moment, and others, again, like me, just want decent food without a lot of fuss. There's no right or wrong here, but there's definitely the potential for conflict if expectations don't line up.

One way I try to manage this is by balancing out our days. We might have a big activity one day and the next day just chill. And if some people wanna be adventurous while others relax, that's okay too. On a sea day on the cruise ship, if some people want to sleep in while others want an early start, the early birds can grab breakfast without waiting around. If we're going out to dinner every night, we might alternate between a fancy sit down restaurant one night, and counter service the next night.

And look, sometimes someone's just having a bad day. We've all been there. Travel is tiring and being around family constantly is exhausting even when you love them. Jet lag is real. Heat is oppressive. Somebody didn't sleep well. Your teen is homesick or they miss their friends.

If somebody's grumpy or withdrawn, try to give them space if you can. Don't take it personally, but also don't force cheerfulness. Sometimes people just need to reset and they'll be fine tomorrow.  The biggest lesson I've learned about managing interpersonal dynamics on our multi-gen trips is this: you cannot make everyone happy all the time. But you can be thoughtful about planning, and you can communicate clearly and build in flexibility, and then just extend grace when things get tense. If you do those things, most of the interpersonal stuff resolves itself, or at least it doesn't blow up into a major conflict that ruins your trip.

So let's pull this all together. Multi-generational travel can be incredible. It creates memories that last and strengthens family bonds. It gives far-flung cousins time to really reconnect and and let's grandparents be present for experiences they'll treasure. I know my kids look forward to this every single year, but it requires a lot more planning, more communication, and more flexibility than just traveling with your immediate family.

Here's my advice. If you're planning your first big multi-generational trip, start small if you can. If you're not sure how it's gonna go, don't commit to two weeks in Europe with 12 people moving from place to place every day. That's a lot.

Even if you're experienced at multi-gen travel, try a long weekend somewhere closer first. See how the dynamics play out with that specific group because they're always different. Learn what works and what doesn't before you invest in a bigger, more expensive trip. Be really clear about expectations, dates, costs, who's paying for what, what's included and what's not. Have those conversations early and make sure everyone's on the same page before you book anything.

Choose destinations and accommodations that naturally accommodate different needs and activity levels. Cruise ships, all inclusive resorts, places with lots of excursion options. Those work really well if you're just getting started as multi-gen travelers because there's something for everyone without constantly negotiating.

Build in flexibility. Don't try to keep everyone together for every single moment. Let people split up by interest or energy level. Pick the moments that matter for togetherness. Maybe it's dinner most nights, but leave the rest loose. If you can, book early especially if you're using points, and set clear deadlines for when people need to commit so that you're not stuck holding the bag if someone backs out after a cancellation deadline has passed.

Consider using a travel agent for more complex trips, especially if you're navigating challenging family dynamics or you're not sure exactly which property or cruise will work best for your group. And finally, extend grace- to yourself, to your family members, to the situation.

It's not gonna be perfect. Someone is gonna be grumpy At some point, plans will change, a flight will get canceled, things will go wrong. That's travel and that's family. But if you're thoughtful about planning and flexible in execution, you can create trips that everyone looks back on fondly. The teenager might have complained about spending time with little cousins in the moment, but years later, they'll still remember that trip. The grandparents might have slowed the group down, but they got to be there with everyone, and that matters a  📍 lot.

 Multi-gen travel is about creating shared experiences across the generations. It's messy and complicated and sometimes frustrating, but it's also really special.

As we wrap up, I'd love to hear about your multi-generational travel experiences, what's worked for your family and what's been challenging, any lessons learned that might help other families. You can find me on my website, thefamilyvoyage.com, or leave a comment here. If you found this episode helpful, be sure to give it a like and a five star review and share it with anyone you know who's planning a big family trip.

This stuff is hard and we're all figuring it out together. Thanks for listening and happy travels.