Planning a Multi-Generational Family Holiday? This Is Where It Gets Complicated

The hotel that looks perfect might not actually work 

This is probably the biggest thing with multi-generational holidays. A hotel can look absolutely perfect online. Beautiful pool, lovely beach, family rooms, kids' club, several restaurants. On the surface, we've ticked everything.

Then I start digging into whether it actually works for the family travelling.

Perhaps the family rooms technically sleep four but give the parents almost no privacy. Maybe the kids' club is brilliant for the youngest child but there's very little for the teenager. The resort might be stunning but built into a hillside, which suddenly matters when a grandparent isn't particularly mobile. Or the room types everyone needs are scattered across different parts of a huge resort.

None of those things necessarily makes it a bad hotel. [P] It just makes it the wrong one for that family.

Family-friendly doesn't tell me nearly enough

I see family-friendly used to describe everything from small hotels with a children's menu to enormous resorts with waterparks, clubs for different ages, sports academies and entertainment from morning until night.

So when somebody tells me they need a family-friendly hotel, that's really only the beginning of the conversation. 

A five-year-old, a 12-year-old and a 16-year-old can all be travelling on the same holiday and need completely different things. Add parents and grandparents and suddenly family-friendly needs to stretch quite a long way.

That's why I don't simply search for hotels labelled good for families. I match the hotel to the actual family.

Sleeping everyone is the easy bit

Finding accommodation that technically sleeps six, eight or ten people isn't necessarily the difficult part.

Finding accommodation where everybody has the right amount of space and privacy is where it gets more interesting.

Sometimes a villa is absolutely the answer. On another holiday, several rooms or suites close together work much better. Interconnecting rooms can be perfect for one family and completely unnecessary for another.

I also look beyond the number of bedrooms. Bathrooms, living space, who's sharing with whom and how the family will actually use the accommodation can make a huge difference.

A room description might tell me how many people it sleeps. It doesn't tell me whether I'd actually want to put my clients in it for ten nights.

And no, you don't necessarily all need to live together

I think there's a lovely idea attached to a big family holiday that everybody should share one enormous villa and spend the whole week together.

For some families, that's perfect.

For others, separate rooms and a little bit of space are exactly what keeps the holiday lovely.

Grandparents may appreciate being able to disappear for an early night. Parents might want their own space once the children are asleep. Teenagers quite like the idea of not being permanently attached to the rest of the family.

Travelling together doesn't have to mean being together every minute.

Sometimes the best multi-generational set-up is one that makes it really easy to come together and equally easy to disappear for a couple of hours.

The children can completely change my shortlist 

Tell me you're travelling with children and I still don't know enough.

Their ages matter enormously.

What works brilliantly for a family with a four and six-year-old may be completely wrong for one travelling with a 12 and 15-year-old.

This is why I look beyond whether a hotel simply has a kids' club or children's facilities. I want to know whether what's there is actually relevant to the children travelling.

If keeping the children occupied is important to the holiday, that becomes part of my hotel search from the beginning rather than something we discover after booking. 

Teenagers are often the ones people forget

Younger children are usually quite well catered for in family resorts. Teenagers can be a different story.

They're too old for anything that feels childish, but they still want something to do. And if you're away for ten nights or two weeks, a pool and decent Wi-Fi might not be enough. 

So if teenagers are travelling, I'll be thinking about whether there's enough for them as well as everyone else. That might completely change the hotels I'd recommend. 

A resort can be fantastic for families and still be the wrong family resort for your family.

Grandparents don't automatically want peace and quiet

I don't plan holidays around stereotypes either.

Sometimes the grandparents are the ones who want to be out every evening while the parents would happily be in bed by ten.

Age doesn't tell me whether someone wants a quiet boutique hotel, a lively resort, an adults-only pool or a bar with music after dinner.

What it can tell me is that certain practical things may matter more. Distances around a resort, steps, hills, room location and how easy it is to get to restaurants or the beach can suddenly become important.

That's the sort of detail I want to know before I recommend somewhere, not after you've arrived.

A gorgeous resort can be surprisingly hard work

Some of the most beautiful resorts are enormous.

That's not necessarily a problem. A large resort can be brilliant for a multi-generational family because there's enough going on for everybody to have a different day without leaving the hotel.

But I also want to know how that resort works.

Where are the rooms in relation to the restaurants? How easy is it to reach the beach? Is the children's area at the opposite end of the property from everything the grandparents will use? Is the hotel built on a steep hillside?

These aren't the exciting bits of choosing a holiday, but they're exactly the sort of things that can determine whether it feels effortless once you're there.

Food becomes a much bigger part of the decision

One family holiday can involve someone who loves trying everything, a child who would happily live on plain pasta, a teenager who's permanently hungry and grandparents who'd really rather have a good sit-down dinner.

Then add allergies or dietary requirements and the restaurant side of the hotel suddenly becomes rather important.

This is why a hotel advertising five restaurants doesn't automatically impress me. I want to know whether the dining actually works for the people I'm sending there.

The same goes for all-inclusive. For a big family it can make the whole holiday incredibly easy, but only if the particular all-inclusive works well for them.

I don't want clients arriving and discovering that the restaurant they were most excited about isn't included, or that the dining arrangement doesn't work the way they'd assumed.

All-inclusive can be brilliant for a big family

For the right group, I really like it.

Nobody is constantly reaching for their wallet. Children can have a drink or an ice cream without every little thing becoming another transaction. Different generations can have lunch at slightly different times without somebody organising a group of ten people three times a day.

It can take a surprising amount of admin out of the holiday.

But I wouldn't recommend all-inclusive just because there are lots of you. If half the reason you love going away is finding different restaurants outside the hotel every night, I'd rather build the holiday around that.

Easy is only useful if it's also right for you.

One of the best bits is that you don't have to do everything together

This is where a multi-generational holiday can actually become easier than travelling as one smaller family.

The grandparents might take the children for lunch while their parents disappear to the spa. The teenagers can head off to an activity while everybody else goes to the beach. Someone can stay beside the pool while another part of the family goes out for the day. 

Then everyone comes back together for dinner. 

To me, that's a successful family holiday.

You're creating memories together without turning ten people into one travelling unit that has to agree on every single plan.

Sometimes a villa is perfect. Sometimes it really isn't

Villas sound like the obvious answer for a big family. And sometimes they are.

Lots of space, private pool, bedrooms for everybody and somewhere you can all sit together can be fantastic. 

But then I want to know what sort of holiday the family actually wants.

If nobody wants to think about cooking, shopping or organising anything once they arrive, a standalone villa may not give them the holiday they pictured.

That's where villas and residences within resorts can become really interesting. You can potentially have the privacy and space while still having hotel facilities and service around you.

On another trip, several hotel rooms may make far more sense. 

I don't have a default answer. That's the point.

The transfer is part of the holiday too

It's very easy to get excited about the hotel and forget about what happens between stepping off the plane and actually reaching it. 

With several generations travelling together, I think about that journey as part of the overall holiday.

A longer transfer might be completely worthwhile for a really special resort. On another trip, particularly with very young children or somebody who finds long journeys difficult, I'd give it much more weight.

Arrival time matters too. The same transfer can feel very different in the middle of the afternoon compared with after a late flight.

It doesn't mean we always choose the closest hotel to the airport. It means I factor the whole journey into what I'm recommending.

Sometimes the flight decides more than you'd expect 

The same applies before you've even reached the destination.

When I'm looking at a big family trip, I'm not only thinking about which destination has the nicest hotel. 

I'm thinking about how everybody gets there.

If the whole group is comfortable with a longer flight, brilliant. If there are young children, older relatives or people who really don't want a connection, that can change where I look.

There isn't much point finding an amazing holiday that half the family hates the idea of travelling to.

And sometimes everyone doesn't need exactly the same holiday

Even the dates can be more flexible than people realise.

There may be occasions where part of the family stays longer than everyone else, or some people arrive slightly earlier.

If that makes the trip work better around annual leave, school dates or budgets, it's something I can look at when I'm putting the holiday together.

A multi-generational trip doesn't always need one identical booking repeated across every person travelling.

Different budgets need handling carefully

This is one of those conversations that's much easier to have before everyone has fallen in love with a hotel.

If several households are paying separately, there may be different ideas about what feels comfortable.

That doesn't necessarily mean the holiday won't work. There can be different room categories or ways of structuring the trip without making anyone feel awkward.

But I want to understand the budget from the start.

The last thing I want to do is show you something spectacular, get everybody excited and then discover that it only works for half the group.

Too many opinions can make choosing almost impossible

This is probably familiar to anyone who's ever tried to organise a big family meal, never mind a holiday.

One person sends a hotel. Someone else finds another one. An aunt has seen somewhere on Facebook. The teenager wants a completely different country. Somebody's friend stayed somewhere amazing three years ago. 

Before long, the family WhatsApp group contains 47 links and nobody can remember which hotel actually met the original brief. 

This is one of the places where having me in the middle makes the whole thing much easier.

Give me the people, dates, budget and what everybody needs from the holiday. I can do the filtering rather than the whole family spending evenings disappearing down Google rabbit holes.

I don't need you to find the hotel before you contact me

In fact, I'd rather you didn't feel that you have to.

You might already have somewhere in mind, and that's absolutely fine. Send it to me and I can look at it as part of the search. 

But if all you know is that there are eight of you, the children are 6, 10 and 15, Nan doesn't want a long flight, everybody wants a lovely beach and you'd really like all-inclusive, that's enough for us to start.

You don't need to know whether Greece, Turkey, Cyprus or somewhere further afield is the answer.

Finding that answer is part of what you're asking me to do.

The bit you don't see when I recommend a hotel 

By the time I send you a shortlist, I want the obvious problems to have already been filtered out.

You don't need a document containing every hotel I rejected because the rooms didn't work, the location was wrong, the facilities didn't suit the children's ages or the overall holiday wasn't good enough for the money.

You need the options that I think genuinely fit.

That's one of the biggest differences between having hundreds of hotels appear in a search result and having someone actually recommend a handful to you.

More choice isn't always more helpful.

The cheapest option isn't always the one I'd recommend

Particularly with a big family, relatively small differences can have a much bigger effect once multiplied across several rooms and several people.

Of course the overall budget matters. I work within it.

But I also look at what you're getting for that money.

If one option costs a little more but gives the family a much better room arrangement, food everyone can enjoy and facilities that actually work for all the children, that may be where the value is.

Equally, I won't recommend paying more for facilities nobody in the family is going to use.

The aim isn't to find the most expensive holiday. It's to spend the budget in the places that actually improve it.

The best destination might not be the one you expected

This is another reason I like getting the brief before everybody becomes fixed on one destination. 

Sometimes the place you initially had in mind is absolutely right.

Sometimes I can see another option that fits the family much better.

Perhaps it gives us better rooms for the budget. Maybe the flight works better. There might be a hotel that's far stronger for the children's ages or somewhere that makes life easier for the grandparents without compromising what everyone else wants.

That's when I want the freedom to say, I've found something else and I think you should see it.

Multi-generational holidays are exactly where matching matters

There are holidays where the brief is incredibly straightforward.

A multi-generational trip usually isn't one of them.

There are more people, more opinions, more room requirements and more ways for a hotel that's brilliant on paper to be slightly wrong in reality.

But that's also what makes these enquiries so satisfying to put together.

Once I've found somewhere that gives the children enough to do, gives the adults the holiday they wanted and makes things comfortable for the grandparents, the whole trip starts to click.

You don't need to solve all of this before you enquire

This is the bit I really want you to take away from this guide.

You don't need to research the best destination for multi-generational families. You don't need to compare 20 resorts, work out which room combination you need or spend your Sunday evening reading the small print of seven different all-inclusive plans.

That's what I'm here for.

Tell me who's going. Give me the children's ages, the dates you're considering, an idea of the budget and anything you already know matters to the family. 

If you have absolutely no idea where you want to go, that's fine too. 

I'll take that brief and start doing the matching.

Because the goal isn't just getting everybody away

It's finding a holiday where the grandparents don't feel they've booked a children's resort, the children aren't bored, the parents actually get to relax and nobody spends the whole week wishing we'd chosen somewhere else.

You should be able to enjoy the exciting bit of planning a big family holiday without becoming the family's unpaid travel coordinator.

Give that job to me.

If you're thinking about taking the whole family away, get in touch. Tell me who's travelling, your dates, approximate budget and anything that's already on the wish list. I'll take it from there.

Danielle x