How to survive a holiday with your parents and your children – The Telegraph

From age 11 to age 78, keeping everyone in the family happy on holiday isn't easy – but it might just be worth it
It’s nearly 100F in the shade, there is a queue a mile long and three sets of eyes, aged 11, 13 and 78, are staring up at me mutinously. “We can ‘do’ Paul Revere’s House in 10 minutes,” I say, desperately. “Five, at a push. Now will you all cheer up?” There is a resentful groan. I don’t want to check whether this actually came from my daughters or my mother.
If, like me, you took three generations on holiday this summer, then you are bang on point, thanks to what the travel association ABTA is calling the “travel for reconnection” trend. After two years of pandemic isolation, the travel referral platform Zicasso has seen multi-generational trip bookings go up by 50 per cent, while more than a fifth of Gen Zs (18 to 24-year-olds) say they would rather go on holiday with their grandparents than their friends.
My own multi-gen holiday came about because of a Covid-delayed research trip to Boston to look at the archive of the journalist Alistair Cooke, creator of the BBC’s Letter from America. I’d always wanted to take my daughters, Faith and Alethea, to the US, but my husband’s work commitments meant he couldn’t join us. So, when my mum, Carys, suggested she come instead, I jumped at the opportunity for mother, daughter and granddaughters to reconnect after nearly 18 months apart during lockdown. And Boston seemed a perfect destination – the combination of the glorious beaches of Cape Cod with the excitement of a busy city and some cultural trips thrown in.
Except for the fact that we are all very different. 
My glamorous mother is the sort of woman who’ll order a Greek salad in a burger bar, while my younger daughter Alethea never knowingly ingests a vegetable. I love nothing more than a good mooch around a museum; my daughters shudder at any mention of the National Trust. And most crucial of all, how on earth would four women manage in one hotel room when the 13-year-old needs 45 minutes minimum in the bathroom to do her hair every time we go out?
An inveterate planner, I start by asking an expert – Dr Audrey Tang, of the British Psychological Society (and also the author of The Leader’s Guide to Resilience, which I think could be useful for any future family occasion) about the practicalities. “Multi-gen holidays are a wonderful opportunity for generations to spend time together,” she says. “Your child will always see themselves as your child, but with a grandmother they can see themselves as someone different. And the same goes for your mum and them.”
And for me in the middle? “Just remember that a common mistake is to think that this is going to be a holiday of a lifetime, which can put a lot of pressure on the organiser.”
Tang is clear that a successful holiday of this type has several elements: make sure you don’t do everything together, and that everyone chooses what they want to do – not from a checklist that I provide, but things they discover themselves. No vacation without representation, as the Founding Fathers might have said, if they’d grabbed their extended families for a trip round Yosemite after penning the Constitution.
So, I had only myself to blame when wildly different suggestions came back. My mum fancied a sunset cruise round Boston Harbour, and to sip a cocktail in a classy bar. The girls plumped for visiting Target, the American superstore they’d heard about from their friends. Meanwhile, I was up for ticking off the Isabella Stewart Gardner Museum, home of the biggest unsolved art heist.
But despite Tang’s advice that we should all contribute ideas, the fact is that someone still has to book the Duck Tour, tip the porters and adjudicate on diner versus seafood for supper. And that was one of the most illuminating parts of the holiday for me. One day, I found myself getting particularly stressed, shepherding everyone on and off the “T” (Boston’s public transport system) and choosing the route to see Harvard. Until I realised that, although I have a mortgage, a family of my own and an overdraft, somehow I’d subconsciously regressed, expecting my mum to be in charge of us all.
But the trip was my idea – and I was the one with the apps, the credit card and the O2 bolt-on to make it happen. “It’s so lovely having someone else organising stuff,” my mum said the third time I’d misread the Citymapper app, taking us 20 minutes’ walk in the wrong direction.
And that was fair enough. My parents had two decades of bundling me and my three siblings into the back seat of a Renault 5 to rain-swept holidays in north Wales, Eastbourne and once, memorably, a camping trip to the Forest of Dean, when we discovered my brother suffered from claustrophobia in tents. There was no reason my mother should have to make any decision other than debating between the joys of a Leave It To Me cocktail or a Signature Martini in the historic Street Bar at the Newbury Hotel.
Meanwhile, it was me who’d ignored the sound advice of Tang that we didn’t have to do everything en masse – hence the rebellious looks outside Paul Revere’s house during a heatwave. Yes, Paul, the British were coming – but very, very reluctantly.
The other illuminating issue was money. As Dr Joan Harvey of Newcastle University points out, our three generations have different attitudes to budgeting. “The older generation are likely to have been brought up careful with money,” says Harvey. “That level of thrift won’t apply to your generation who tend to go for instant gratification but may well be maxed out on credit cards. Whereas the younger generation just can’t afford major purchases so they spend what they earn on drinking and eating out.”
The truth is, I haven’t told my mother the correct price of anything I’ve bought since a Top Shop sale in 1994, for fear of appalling her with my wastrel ways. So, working out the budget was one of the most excruciating parts of the holiday for me. Mind you, perhaps I should have taken a different view, as Harvey, a boomer herself, notes: “People my age want to spend their money on ‘experience goods’ – and they often have more disposable income to fund such trips for everyone. Why would I want to buy another toaster or set of spoons when I could be making memories?”
Fortunately for my mother (and her bank manager) I didn’t take Harvey’s advice here literally by suggesting she pay up for all of us. But Harvey was absolutely right that the experience was what mattered most – and our best ones were often unplanned. The kids laughing hysterically when a stray wave on Race Point Beach in Provincetown, Cape Cod left my trousers soaked. Reconstructing scenes from Legally Blonde in Harvard Yard rather than debating university admissions. A fierce fight over who had won an ancient Egyptian game in a new immersive Tutankhamun exhibition. And the rather too candid remark from one of my daughters when discussing how to make a statue of me after seeing the ones in the Gardner: “Yes but to sculpt one of you, we’d need a lot more clay.”
Even the scavenger hunt which seemed to take in every single monument in Back Bay proved a giggle due to our inability to follow it. But this was mainly thanks to the fact such digressions gave my mum time to use family sayings the girls had never heard before – their favourite being my grandmother’s Welsh Presbyterian response when invited to any upcoming event “Yes… if the Lord spares me.” (She’s now 101).
“I always say to people, remember why you’re doing this,” says Tang. “If it’s because you want to spend time together, then it doesn’t matter if you’re spending time together visiting the re-enactment of the Boston Tea Party or lazing by the pool. Keep that ‘why’ in mind.”
So next time I will take all advice to heart. I won’t plan anything, we can all do our own thing and, yes, Mum: you can pay.
Once you’ve seen Minnie and Mickey, there’s a surprisingly broad variety of attractions for parents and grandparents. Visit the Orlando Ballet or Philharmonic. Less than an hour from the city you’ll find the Everglades, natural springs and excellent beaches. The shopping’s good, too. Click here for The Telegraph’s pick of the best hotels in Orlando.
There’s more to Zakynthos than house music and cocktails, with the northern half of the island now a destination for discerning families. Head to the Peligoni Club which boasts great restaurants and, for the teens, Shipwreck Beach – the most Instagrammable cove in the Med and only reachable by boat. See peligoni.com.
Heidi-style mountain adventures and decadent spa hotels, few holidays cover all the bases like the Swiss Alps. The Grand Resort Bad Ragaz boasts hot tubs, saunas and steam rooms, golf courses and a casino, plus a family-friendly water park. See resortragaz.ch.
Always a solid bet when you have various ages to please – particularly if you base yourselves at a well-placed villa (try purefrance.com). Little ones will love the Plage du Port Gallice and Plage de l’Escalet, while the rest of the family can enjoy the rambling vineyards, castles, museums and quaint hilltop villages.
No need to venture far for this spectacular stretch of coastline, replete with geological wonders and pretty seaside coves, Take the brood to The Pig on the Beach (pighotel.com) in glorious Studland Bay, and you’ll be in easy reach of Corfe Castle, the Jurassic Coast and a host of excellent museums, including Swanage Railway Museum and Purbeck Mining Museum.
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