Multi-Generational Vacation Tips (From Real Trips with my Real Family)

It’s Day 3 of our family vacation. My goddaughter has just scaled the stairs to the highest waterslide in the park. I watch in amazement, in awe, with pride, to the little 7-year-old come down the slide all smiles, jumping up to do it again. Only two days ago she wouldn’t even try the kiddle slide. Look how far she’s come! These are the moments family trips are made of. This is what a multi-generational family vacation can be, when you plan it right.

Having traveled not just with my parents, but with aunts, grandparents, cousins, nieces and goddaughters, I’ve experienced how special multi-generational family vacations can be. With the holidays approaching, many people may be planning their own multi-generational getaway.

Planning trips for a group of people with such a wide age range, varying vacation expectations, and energy levels is tough. Add the whole family dynamic, and it can be a recipe for disaster – believe me, I learned the hard way! Good news is I learned my lesson, lived to tell about it, and now I’m here to show you that with a little extra care, you can plan an amazing trip that your entire family will never forget.

Why a Multi-Generational Family Vacation Matters Right Now

Time flies by before we know it. That 7-year-old that went down a waterslide is now living her best nonchalant pre-teen life. If we don’t seize the moment to spend time with each other now, travel with each other now, we may miss the moment. Even if we go later, it will be a completely different experience because everyone is at a different place in their lives.

The Clock We Don’t Like to Talk About

When I think of my fondest memories of my grandmother, one of them is seeing her strolling the streets of Spain on her newly replaced knee. I was studying abroad for a year, and my parents and grandma came over for Thanksgiving – sweet potatoes, cranberry sauce and stuffing in tow (luckily, we could order a turkey from the butcher – yes, please pluck her and no, the head, feet and neck are not needed, but thank you for asking!). It was such a special moment to have my family and my host family united for a holiday that’s all about, well, family. It was also special to see my grandmother on a trip, as most of our time together was spent back at home.

Luckily my grandmother lived for nearly 20 years after that, but it wasn’t too long after that trip that she started deteriorating a bit. She eventually got dementia, and I’m not really sure how much of the last ten years of her life she even remembers. Had they not taken that trip when they did, I’m not sure it could have happened again. For that, I’ll always have an amazing memory and will always be grateful.

That’s my long-winded way of saying, stop delaying. Take the trip. Make the visit. You may not get the chance later.

What Kids Actually Remember

That goddaughter of mine on the waterslide? That was actually on a multi-generational family vacation to Disneyland (and no, the Diz does not have waterslides, but our hotel did). And you know what the highlight of their trip was? Not Disneyland. The waterslides.

It just goes to show kids are not interested in the expense of things, or the name brand aspect of it. OK yes, kids may be interested in the moment, but what do they remember years from now? They remember the experience they had. They remember the people they were with. That’s the stuff that matters.

The Gift You’re Really Giving

So, what does this equate to? You’re not just giving your kids a leg up on stamps in their passport. It’s not about getting grandma to pipe down about finally visiting that place she’s always wanted to see. You’re actually giving everyone – yourself included – the gift of time together, of memories, of deepened bonds. Is it hard to coordinate across three generations and 4 family branches? Absolutely! But the payoff? The payoff is so worth it.

The Honest Truth About What Makes This Hard

Yes, I have fond memories of my multi-generational family vacations, but I also have some battle scars from dealing with what can make these trips difficult!

Everyone Wants a Different Vacation (And That’s Normal)

Mom is looking for an exciting adventure. An aunt wants a relaxing vacation. A cousin wants pub crawls, and the teens just want WIFI for their gaming. So, what’s a multi-generational trip planner to do?

Consider everyone’s input and look for destinations that can fit multiple needs. Forcing everyone into one style of vacation won’t make everyone happy – and in fact, will likely have family members bowing out. Instead, focus on the short list of must-haves and must-avoids for everyone. Dad doesn’t want anything too hectic? That packed itinerary with outdoor adventures every day is a hard pass.

It’s actually easier than you think to design a vacation that can fit the desires of multiple people – or at least give the flexibility in the itinerary to allow that to be the case.

The Energy Gap is Real

The type of vacation people are looking for may also correlate to their energy level, or lack thereof. If grandpa is in a walker, he’s not going to have the energy or stamina for a New York trip that clocks 20k+ steps a day. Similarly, a weather wimp like me who has never skied will have to give serious consideration to a ski trip (I’ll be the stay-puff marshmallow at the bunny slopes).

Thinking through this when you’re planning the trip and itinerary is really important, as it will help ensure everyone has a good time.

When Someone Needs to Be in Charge (But Nobody Wants to Be)

When you’re wrangling a large multi-generational group, someone needs to take the lead. Will it be the patriarch of the family? How about the matriarch? Or the cousin who loves to travel and therefore gets into the nitty gritty of planning (I can relate)? It doesn’t really matter who it is, as long as it’s clear to folks who is driving the planning.

Sometimes strong personalities will come in and dominate or steer planning in another direction. My advice is to be open to different perspectives, and be open to parallel plans (more on that later), but if you know the majority is in favor of the plan that’s in place, find a way to kindly convey that….and be prepared for any past family hangups to rear their ugly head. More on that later, too!

Money Gets Weird Across Generations

When you’re working with a multi-generational crew, or doing the planning for your own family tree, money can be interesting. Typically challenges that arise here are about people not wanting to be a burden or wanting to be the caretaker and pay for things. It’s more about sentiment than finances. The key is to validate everyone’s perspective, while looking for ways that can make everyone feel great about the outcome.

Who’s Buying?

Some adults now want to pay their own way, showing their independence. Some parents want to still cover the cost of their children as they always have – whereas other times, the roles start to reverse. Is grandpa dead-set on covering the hotels? Great, be thankful, and let him know you and your siblings will cover meals and activities.

There’s no one right way to split up costs, but the one thing you do want to get right is how people feel about it. Years from now, people won’t remember how much they spent, but they’ll remember how they felt about how finances were handled (especially if handled poorly). Your goal is to make this so seamless, there’s nothing unjust to remember at all!

How Much Can People Afford

Once you align on how costs will be split up, you also need to understand how much people actually have to spend. That budget question is a big one that can be a dealbreaker. I found this out recently when I started planning a family trip to celebrate my grandmother’s birthday. She had wanted to see Hawaii, and can’t walk too far, so we opted for a cruise. Everyone seemed up for it, and we aligned on dates, so I booked a block of rooms. Turns out, we didn’t get into specifics about the costs once people added flights, activities, etc. It ended up blowing up the trip because we didn’t want to leave people out. Luckily cabins were fully refundable, but I learned to get a bit deeper into these types of questions when planning.

The Foundation Conversations (Before You Book Anything)

Before you jump to it and start booking hotels and activities, take a beat and meet. You want to connect with the fam to get the lay of the land. These foundational conversations will make planning the trip – and enjoying the trip – much easier!

The Family Meeting that Changes Everything

When you connect as a family, you can get aligned on some core components of the vacation. Is this trip celebrating something special? If it’s for someone’s birthday, maybe they get two votes on the destination. You can chat through those energy levels and what type of vacation everyone is looking for.

You’ll want to ensure everyone has a voice, even the kids and the older generation. For kids, maybe they weigh in on types of activities they want or types of weather they’re looking for. For the older generation, perhaps there’s places they’ve always wanted to see; or wisdom they can share about places they’ve already been. Either way, it’s great to get input from everyone so the whole family feels invested in and excited about the trip.

Questions You Must Ask (Even the Awkward Ones)

During this meeting, it’s key to get into the (sometimes hard) questions. What budget are people comfortable with, how much time can people realistically take off, and when?

Another important aspect are physical realities beyond the energy levels we need to think about. Mobility issues, medical needs and dietary restrictions can all impact your vacation choices. My 80-year-old father, as an example, can walk just fine. But walking long distances can be tough. We’ve found it’s easier at the airport to use wheelchair assistance. It was a tough thing to do at first and was hard for him to accept the help. But ultimately it made traveling easier for everyone, and less strenuous for him.

Not understanding this up front can either exclude people from a vacation or derail the vacation completely.

Choosing Destinations for a Multi-Generational Family Vacation

Now that you have the basic structure and parameters outlined, along with ideas from the group, you can pick the actual location. This could be as simple as doing it during the family meeting after someone pitches an idea, or it could take a bit more discussion and research.

The Goldilocks Zone: Not Too Much, Not Too Little

The key here is to look for commonalities across the ideas, or places that can accommodate a variety of needs. It can’t be so mellow the kids get bored, but it can’t be so packed that mom and dad can’t keep up. Some good options here include all-inclusive resorts or cruises, which typically have plenty of kids programming, water activities, and plenty of places to chill for the folks that want a breather. It also gives people a chance to do their own thing and meet up for dinner or key activities, padding in that alone time people may want.

If your family is aligned on a more outdoor-themed activity, renting a shared house in or near a National Park, or at the beach, can be a nice way to get together. The more active can hike, swim, or surf, while others can relax at the house. This is where location flexibility really shines. We once rented a house near Yosemite. My mom, close family friend and I would tackle day hikes, while my dad did more mellow walks along the lake near our cabin. Same destination, totally different energy levels, everyone happy. The shared house allowed for reconvening for meals, but nobody was forced into activities they’d resent (or couldn’t do).

When Locations Makes or Breaks the Trip

As you’re planning this trip and picking your location, there are some things to avoid. If you’re working with a large multi-generational group, try to avoid anything that requires extreme coordination. The more logistics and coordination, the more things can go awry. 5 flights to get to that iconic island during hurricane season? Probably not the group to risk it with.

If you have older folks in your group, or people at heightened risk of needing medical care, you’ll want to make sure you have that close by. Similarly, if Grandpa can’t handle a flight over 4 hours, that narrows down where you’ll want to go. We’ve had to rule out locations plenty of times due to these basic but critical components.

Cities can be a little harder for people with mobility issues, or who just want less activity. That said, don’t write off cities completely. We did a large family trip to Las Vegas, and the key was having a home base (we rented a house) and letting everyone choose their own adventure. The younger cousins went out to enjoy all the Strip has to offer, we all caught the Nascar races and visited the Neon Museum together, and the older generation opted for quiet meals out. Staying at a hotel would have worked too – the key to success is giving people proximity without forcing participation.

The Underrated Power of Proximity

Believe it or not, sometimes you don’t have to go all that far to get together. Locations closer to home are often more budget-friendly, time-friendly, and family-friendly. You may remove the need for a flight, make it easy for folks to come in on their schedule, and it can feel more accessible. We rented a house in Palm Springs one week, which is about 1.5 hours from where we live. It was a great getaway, where again everyone had time for the activities (or lack thereof) that they enjoyed. We cooked most meals at the house, enjoyed the pool and played games. It was a lowkey multi-generational getaway that didn’t break the bank or use up everyone’s vacation.

We’ve even talked about renting a beach house here in San Diego. Remember, the intent of a multi-generational family vacation is less about where you go and more about the memories you make. If you’re together, removed from the distractions of day-to-day life, you can make these memories anywhere.

Planning an Itinerary That Doesn’t Make Anyone Miserable 

Now that you have everyone aligned on where you’re going, now you get to decide what to do – or what NOT to do! Again, working with multiple generations, multiple desires and expectations, this really is key to a successful trip.

The 50-30-20 Rule for Multi-Gen Success

One guideline that can be helpful is the 50-30-20 rule. This is basically an outline as to how to plan time together vs apart. 50% of time can be planned group activities – think meals, photo sessions, games, or activities everyone can participate in. 30% can be optional activities. Some people want to do a pub crawl; others want to do a hike. There’s no pressure to join, but the invitation is open. The last 20% is completely free time. People can go solo or make plans with a smaller group on their own if they’d like.

When to Plan Everything vs Nothing

Here’s a potential structure to consider:

• Mornings: flexible, people can eat on their own based on when they get up and going (part of the 20%)
• Afternoons: The key anchor events, like taking a sunset cruise, seeing a show, or going to a race, are identified and planned ahead of time (the 50%). Other activities can be decided closer in, based on who’s interested in doing what (the 30%).
• Evening Ritual: Maybe everyone agrees to meet for family dinner and photos at sunset. (part of the 50%)
• Respect Rest Time: that 20% is small but sacred. Let people take what they need, whether they’re 8 or 80. You can also build in complete rest days, so folks have flexibility on what they want to do.

The Art of the Elegant Split-Up

Splitting up doesn’t have to be a bad thing. In fact, in my experience, I’ve found people really enjoy it. For the 30% optional activities, you could have an A team – the ‘active’ team – and a B team – the ‘be relaxed’ crew. If you’re traveling with teens or kids, let them pick one of these activities – it’s their vacation too! Each group can do their own thing during the day and meet up for those agreed-upon meals or activities. That also takes pressure off of you to have to plan every single detail.

Here’s how this looked in real life: When I went to Puerto Vallarta with my mom, friends, and cousins, we naturally fell into this rhythm. We usually had breakfast separate as we were on different sleep schedules (part of our 20% free time), met up at the pool for a bit (50% group time), separated in the afternoon with some of us seeking shade, massages or sleep while others explored (30% optional activities); and then reconnected in the evening for dinner and activities (back to 50% group time). It was a great blend that gave us the together-time we craved while still allowing for the activities we enjoyed.

The Logistics that Save Your Sanity 

Logistics will vary from trip to trip based on where you’re going and how many people you have, but you’ll want to give thought to these recurring themes.

Rooms, Bathrooms, and Personal Space (Oh My)

Are you renting a house with 12 people but 1 bathroom? That’s a recipe for disaster! Think about the bathroom-to-person ratio. People may be more comfortable sharing rooms, but there’s only so long a person can wait for the loo. Also give thought to room arrangements. My family and friends are usually pretty open to sharing, but I have some friends that would prefer to have their own room. If that’s the case, you’ll want to factor it into the logistics selection.

Are you traveling with kids? Is there enough room for them to play outside, game inside, and the like? It’s a good idea to think about kid zone space vs adult zone space, so each have their needs met.

If accommodating everyone’s logistic and space preferences in one house isn’t possible, it’s worth thinking about multiple houses or a hotel. Sometimes being close to each other is better than staying with each other – especially if it’s going to cause more stress than serenity.

The Transportation Situation

Another consideration is transportation. If you’re driving in, people may have their own cars. If flying to a resort or going on a cruise, you may not need a car at all. Other times, it’s helpful to have your own wheels. If that’s the case, can you all fit in one car, or will multiple be needed?

If you are flying, consider timing and logistics – are people flying in at different times, or are they all on the same flight? Coordinating everyone on one flight may be difficult, so it’s ok to come in separately, just chat through what happens once they arrive. Will someone form the group pick them up? Will folks wait for each other at the airport? Or will everyone make their way to the meeting spot/house on their own once they arrive?

I’ve had trips where we all caravan together; where we all fly on the same flight; and where we come in at different times and meet at the rental house. All have worked well, especially because we aligned up front on how it would all go down!

Meal Planning Without Becoming a Short-Order Cook

With so many people having dietary restrictions these days (me included), meal planning can be an interesting consideration. Again, all-inclusive resorts and cruises will make this a lot simpler for you!

If you’re in a vacation rental, I’ve found it helpful to do a grocery store stop on the way in, getting basics for breakfast, snacks, and beverages. We may split up the cooking, a different person in charge of dinner each night; and then add in a couple of nights out. This allows for any necessary purchases or modifications for those that need it. If you are eating out with a large group, I highly recommend restaurant reservations so you can eat at a decent time. Nobody wants a hangry family!

Handling Moments that Go Sideways 

When you’re with a group that has a wide array of ages and personalities, and then add to that the unknown – and sometimes uncomfortable – aspects of travel, you’re bound to encounter some bumps along the way. One of my cousins likes to get right on the road and head out the last day of a trip, while my aunt and grandma love a leisurely breakfast and sightseeing to extend their vacation as much as possible. Let the tension ensue! We’ve since learned it’s best to have two separate cars so the early crew can head out, while the roamers can roam to their heart’s delight. Here’s some other moments that might put a wrinkle in your trip.

When Old Family Dynamics Resurface

We all have them. Those triggers that set you off. Those moments that take you back to being 12. Who else knows how to best push your buttons than your family? They’ve had the most practice, after all! As weird as it is, we’re all guilty of falling back into our old role and patterns when we’re around our family. Sibling rivalries flare up, mother-daughter frustrations arise, the ‘black sheep’ feels called out at every turn. When these situations arise – as they likely will – remain calm and create space for separation, and for venting. Maybe take a walk with whoever is frustrated, let them know you can empathize with their situation. Sometimes just a late-night porch talk and feeling heard is enough to reset the tone of the trip.

If it’s a small enough issue, this should suffice, and you can then let it go. Larger issues may need addressing between the parties. If something significant has occurred that has injured both parties and the broader group, a group discussion once everyone has calmed down may be warranted. I’d only do this after folks have had time to cool down, though.

So that people don’t feel ganged up on, designate someone viewed as a neutral party to guide the conversation and explain how actions have hurt individuals and the group. When we’ve done this as a family, there’s usually some initial though hesitant apologies. While not perfect, it’s enough to allow the group to resume the trip and leave this incident behind. Believe it or not, sometimes these are some of the memories we laugh about years later. That’s the beauty of a multi-generational family vacation – memories are always being made!

The Medical Emergency Protocol

When traveling with family members who have heightened medical risks, it’s a good idea to know where the local hospitals are, what the local emergency numbers are, and the best way to get transportation if you don’t have a rental car. In the awful event you have to take someone to the hospital, ensure they have someone to travel and stay with them. Being in a hospital can be scary anywhere, but even more so when you’re far from home or in another country. If you’re in a place where English isn’t the primary language, have an app like Google Translate downloaded with the local language. That can help you communicate with the medical staff and vice versa.

Permission to Change Plans

You did it. You picked the ideal location, wonderful accommodations everyone loves, created an amazing itinerary with the right mix of together and alone time, and then bam! A storm rolls in and 3 of your outdoor activities are scratched. This is a great example of when to control the controllables – and this one’s out of your control. Rather than letting it get you down, let yourself pivot.

What indoor activities can you come up with instead? Sunset cruise traded for an indoor cooking class; horseback riding traded for a day of board games; there’s plenty of ideas out there. The key is to be flexible and not get so married to one plan that you’re afraid to deviate when necessary.

The same is true if someone is having a horrible time. Forcing them into activities isn’t going to help matters. If you’ve done all you can to add things they may enjoy, make them feel welcome and comfortable, and they still want to leave, the best thing you can do is let them. They likely know what’s best for them and leaving early may help them maintain their family ties long-term.

Capturing Memories (Without Living Behind a Camera) 

When on the trip, it’s important to live in the moment. At the same time, you’ll want some memories captured to look back on.

The Photo Strategy That Gets Everyone

Think about how to get a few posted group shots but allow the majority to be more candid. Identify a few people in the group who enjoy taking photos so all the pressure isn’t on one person. Then, create a shared iPhone photo album where everyone can upload photos to.

Beyond the Camera Roll

Besides capturing candids, you can capture memories in other ways. Each night during group dinner, have everyone share their Peak and their Pit of the day, or at the final night for the whole trip. Ask people to share family stories others may not have heard or have a game where you ask open-ended questions to learn more about each other. What’s the biggest highlight of your life, or your one regret; do you prefer mountains or ocean, and why? These are all ways to make the vacation special while getting to know each other better.

The After-Trip Follow-Through 

You’ve made it home, hopefully relaxed, refreshed and ready for your next multi-generational family vacation.

Settling Up Without Family Drama

However you decided to split up expenses, now is the time to settle up. Share the final expense summary within a week of returning. If splitting costs, Splitwise is a great app to help manage this and share out the total easily. It also allows for easy payment between people. Be kind and patient with different payment schedules – this is family, after all. They’re good for it – and if they’re not, you know where they live 😉.

Keeping the Connection Alive

Share out that digital photo album, and for people that still like a printed album, you can even have one created to share – these make a great holiday gift post-trip! Sending thank you notes to people sharing what the trip meant to you is a nice touch. And if it didn’t happen on the trip, teeing up the idea of planning the next one could be a good next step – though it’s also ok if everyone needs a breather before diving into round two! Savor the time you just got!

Conclusion

Years from now, my goddaughter won’t remember the hotel star-rating or the Disney rides. She’ll remember the feeling of conquering that waterslide with me cheering her on. Your parents won’t remember the group text logistics nightmare – they’ll remember everyone gathered around the table, three generations laughing at the same joke. That’s what you’re really planning: not a trip, but a thread in your family’s story. Make it a good one.

If you’ve been putting a multi-generational family vacation off, this is your message from the universe to give it a go! Are you still hesitant? I’d love to hear what’s holding you back. If this could be a stress-free trip, what would your ideal multi-generational vacation look like? If you’re ready to go but unsure of how to plan, give me a shout. I’m happy to help with custom trip planning assistance.

Wherever you go, however you do it, I want you to have a trip to remember.

Happy travels, Kindreds!

RELATED POSTS

Ready to go?

• Want even more reasons to take a multi-generational family vacation? Read my article about What I learned Traveling with Mom
• Why not make it an all-girls family vacay? Take a look at 6 life-changing benefits of female travel.
• Want to be ready with ideas on where to go? Take a look at my Favorite Fall Destinations and 18 Best Girls Trip Destinations
• Planning around Thanksgiving? Here’s my Thanksgiving getaway guide
• Considering a desert getaway? If you’re wondering whether to visit Palm Springs or Palm Desert, this will help

HELPFUL LINKS

• Custom trip planning: Need help planning your fall getaway? Contact me here for personalized itinerary assistance!
• Want more information on the benefits of using a travel advisor? Learn more here
• Restaurant Reservations: Great to book reservations for meals on OpenTable and Resy https://www.opentable.com, https://www.resy.com
• Car, activity and hotel bookings: https://www.expedia.com, https://www.viator.com
• Hotel and activity comparison: https://www.tripadvisor.com
• Favorite luggage: I love Away luggage, and their bigger carry-on is perfect for family trips where you may need to bring extra items: https://www.awaytravel.com
• Travel planning app: TripIt is great for keeping all your bookings organized and keeping people up-to-speed: https://www.tripit.com 
• Expense splitting (if going with friends): Splitwise https://www.splitwise.com 
• Small group tour companies, great for family getaways – all highly recommended!
  • Intrepid Travel: https://www.intrepidtravel.com
  • Salamander Adventures: https://www.salamanderadventures.co.uk/
  • Wild Sage: https://www.wildsage.it/