How to Plan a Multigenerational Holiday (Without Losing Your Mind)

Start with the WHY, not the WHERE

We love jumping onto Google Maps and Pinterest and saying: “Where should we go?” but with a multigenerational trip the first question should be:

Why are we going?

Is it: 

-            To celebrate Big birthday(s) or special anniversary? 

-            Cousins meeting in real life for the first time? 

-            Welcoming a new baba into the clan? 

-            A long-overdue get-together after everyone scattered to different continents?

That WHY becomes your compass. When things get complicated (and they will), you can come back to it.
Also be honest about the feel of the trip: 

-            Is this a “tick off bucket-list, see new places, do all the things” kind of trip? 

-            Or is this more “sit next to the pool, watch the kids swim, and only move when you need more ice for your drink”?

Your why + your vibe will guide everything else.

 
Getting everyone to the same place (aka Travel Logistics 101)

It is one thing to get a family from Cape Town to Zanzibar. It is a different beast when Cousin Kerry is flying in from Sydney and Oom Louis lives in Toronto.

Things to consider upfront: 

-            Flight times and layovers: How many connections can ouma and oupa realistically handle? Can the toddler survive three flights in a row without everyone needing therapy afterwards? 

-            Meeting in the middle: Sometimes the “perfect” destination is not the dream island, but the place that makes the most sense for everyone’s routing and budget. 

-            Season & weather: A place that is lovely for fit, active adults might be brutal for small kids and oumas in 40-degree humidity.

No destination is worth it if half the family arrives already broken.

Who is coming, really?

Multigenerational does not just mean “some oldies and some kids”. It often means: 

-            A baba that still naps twice a day. 

-            A teen that only really wakes up around 11:00. 

-            Parents who are exhausted before they even leave home. 

-            Grandparents who might need easy access to healthcare and fewer stairs.

Write it out: ages, needs, non-negotiables. It sounds clinical, but it can save a lot of tears later.

Accommodation: Under One Roof or Please Not Even Next Door?

This is where the family dynamics really show up. I have had clients who absolutely love the chaos of one big villa: kids on mattresses in the lounge, oumas making coffee at 5 am, someone always braaing something, everyone in each other’s space all the time. It is like a live-in family reunion and they thrive on it. Then I have had multigenerational groups who were very clear: “Please do not even put our rooms next to each other. We adore each other, but we also adore our privacy. We will meet at breakfast and dinner and for activities, thanks.”

Neither is right or wrong. The key is to be brutally honest with yourself (and with me or your travel planner).

Questions to ask: 

-            Do ouma and oupa need a ground-floor room or lift access? 

-            Do you need interleading rooms for little ones? 

-            Is a cluster of suites around a pool better than one big house? 

-            Do you want hotel-style service (housekeeping, kids’ club, restaurants), or are you happy to self-cater?

Then there is the food question.

Some families love having a private chef or going all-inclusive so nobody has to argue about who is cooking or washing dishes. Others genuinely enjoy cooking together and find that chopping veggies with a glass of wine in hand is part of the bonding.

Know your people.

Money talks: Let’s not be awkward about budget

One of the fastest ways to create resentment in a group trip is to assume everyone has the same budget. They do not. A few honest conversations upfront can save a LOT of discomfort later.

Kids’ ages change prices dramatically. Boetie who is 3 is usually much cheaper than Sussie who is 14. 

Some can afford business class, others are counting every rand. 

Sometimes you get the wonderful situation where Oupagrootjie (great grandparent) has left an inheritance and someone wants to spoil everybody.

If someone is treating the family, that is beautiful, but it also needs to be handled with care and respect for the person paying. What are they happy to cover? Flights? Accommodation? Some meals?

Transparency is not about spreadsheets around the braai. It is simply about making sure nobody rocks up feeling blindsided or guilty.

Togetherness vs sanity: getting the balance right

There is this romantic picture that you will all spend every waking moment together, soaking up every second. In practice, 24/7 together time is… a lot.

The sweet spot looks more like this: 

-            Anchor moments: shared breakfasts, sunset braais, a special celebration dinner, one or two “all in” excursions. 

-            Breakaway time: afternoons where everyone can do their own thing. Ouma naps, teens and uncles hit the slides, parents sneak off for a quiet coffee, someone reads a book. 

-            Optional activities: “boys’ deep sea fishing mission”, “girls’ spa afternoon”, “anyone keen for a hike?” Nobody has to do everything.

Think in terms of rhythm, not minute-by-minute schedules. Enough shared memories, with enough breathing space so no one wants to disown the family by Day 3.

Food, fussy eaters and that one vegan cousin

Food can be such a joy on holiday, but with a big group it can quickly turn into a diplomatic crisis. Picture it:  Oom Piet wants to braai. Every. Single. Night.  Tannie Bev is vegan.  One kid eats only beige food.  Another has allergies.

This is all fine… as long as you know about it before you choose where to stay.

When planning, think about: 

-            Does the resort / area cater well for dietary requirements, kids’ menus, gluten free, vegan, etc? 

-            Is self-catering realistic if you are planning to cook most meals? 

-            Are there enough nearby options that keep things interesting for a week?

Variety and a bit of flexibility will keep mealtimes fun rather than tense.

Ground rules (lightly held) & support systems

Most of us loosen the rules on holiday. Ice cream before lunch, a bit more screen time, bedtimes that slide a little later. That is part of the fun.

But having zero boundaries, especially with small kids and tired adults, can turn even the nicest trip into a meltdown zone.

You do not need a 10-page document, but maybe discuss beforehand: 

-            Rough quiet times for little ones. 

-            How late teens are allowed to roam. 

-            Screen time expectations. 

-            How you will decide on plans when the weather changes or people are tired. 

-            Respect for each other’s parenting styles and personal space.

On a personal note: I love going on holiday with my two adorable nephews. I want to soak up as much time with them as humanly possible. On one trip, my partner and I took the older one for a short hike, ouma and oupa hung out with the little one, and the parents got to nap. Everyone played to their strengths, and everyone won.

That is what you want: a trip where each person gets some proper rest and joy, not just “surviving” the holiday.

Boring but important: practical stuff

Before anyone books a thing, do a quick practical check: 

-            Are everyone’s passports valid for long enough? 

-            Any visas needed? 

-            Travel insurance sorted, especially for pre-existing medical conditions? 

-            Who is flying from where, and are the connections realistic? 

-            Any mobility or health considerations that impact where you can go or stay?

I also love setting up a dedicated family WhatsApp group for the trip. It keeps all the info together, stops things from getting lost in ten different side-chats, and makes it easy to share updates, packing lists and travel photos.

And finally: bring in a neutral grown-up

You knew this was coming… it is my blog after all.

But honestly: bringing in a third party who knows travel, is emotionally neutral, and is not invested in the family politics can save relationships, stress and overwhelm. It also means the organisation does not all fall on the one person who “always ends up planning everything”. Instead of spending hours comparing options online and spiralling with “what ifs”, you can hand over the logistics to someone whose whole job is to: 

-            Listen to your family’s very specific mix of people and needs 

-            Help you find the right destination and style of accommodation 

-            Think through flights, transfers, visas, insurance, room configurations, kids’ ages and grandparents’ comfort 

-            Build in those magic “anchor” moments and enough breathing space 

-            Make sure it is properly protected and bookable

You still get to make the fun decisions and shape the trip. You just do not have to carry it alone.

If you are toying with the idea of a multigenerational holiday with your “not that crazy” family, this is the perfect time to start talking about it. 

Let’s start dreaming together and build a trip that has ouma smiling, the teens actually impressed, the parents rested for once, and Oupa already asking: “So, when are we doing this again?”