Midlifers on tour: why now is the time to holiday with friends again

But the time to do this is not at the end of a boozy meal. Dr Smith suggests discussing such issues before you’ve even gone on holiday. 

“Doing it in advance ensures that the conversation goes really well. It’s about having a plan. If you try to do it when you’re angry, invariably it won’t go well – you won’t be able to get your point across eloquently or compassionately.”

Celebrate common ground

When we get them right, holidays with friends can be enriching, bonding – the best days of our lives. I can clearly recall moments of childhood holidays with family friends as though preserved in a halo of eternal sunshine, and that sense of reckless liberty of those first adventures away from parents with like-minded peers.

Forty years on, my parents are still holidaying with that same crowd. There are 16 of them now – a mix of empty nesters, grandparents, silver-haired bachelors, all in their 70s. They still have lots in common, plenty to talk about. “Although,” says my mother, “these days we spend the first hour discussing our illnesses and medicines.”

Any tips?

“You’ve got to give people space to do what they want to do,” my father says. “And be honest with each other about what you want. That way you can make sure you’re all happy.”

Whether you’re looking to go away with a group of mates, join up with other families or make it a couples affair, read on for the perfect breaks for you.

The friendship group

When you’re young, holidays with friends – whether as singles or a ragtag mix – are invariably hilarious, wildly fun and eventful. What with excessive drinking, little sleep, and living in close quarters 24-7, they can also tip into conflict: things said that cannot be unsaid, people kissed who cannot be unkissed. And why do singles always seem to end up with the sofa bed? By day three, you will have realised there is one incredibly annoying person in the group. (If you don’t, then it’s you.) Yet by the end, you will have bonded more deeply than ever before. Even the disasters will seem, already, like stories to tell.

With age comes wisdom, and a preference for tea and rambling over tequila and raving, which leads to gentler, more harmonious holidays with friends in later life. When choosing a holiday house, the kitchen becomes the all-important hub, and should always be big enough for dancing – at any stage of life.

Where to stay


The new breed of luxury holiday village works brilliantly for big groups of friends, with accommodation to suit all types and sizes, and places to eat, drink, swim and play, together or alone. Soho Farmhouse was the pioneer, but there are an increasing number to choose from, depending on your budget and taste. 

Norfolk’s folksy Fritton Lake suits wild swimmers and nature lovers; while the super-luxe houses of the Lakes by Yoo in the Cotswolds have superstar retreat writ large from jukebox to rooftop pool (Kate Moss, Elle McPherson and Jade Jagger have all designed houses on the estate), plus there’s a spa, pool, zipwire and climbing wall. Fritton Lake (frittonlake.co.uk) offers three-bedroom cottages sleeping six from £980 for four nights. The Lakes by Yoo (thelakesbyyoo.com/stay) offers five-bedroom houses sleeping 14 from £12,000 per week.

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