I figured out the perfect family holiday for teenagers

Telegraph

30-04-2025

If you're looking to test your parenting mettle, try holidaying with teenagers. My three are 19, 18 and 13, with few converging interests. It's still worth it, apparently. Clinical psychologist and parenting specialist Dr Tracy King says, 'Despite the eye rolls, family bonding is still crucial in adolescence. It provides an emotional anchor during a time of rapid change. Shared memories remind teens who they are and where they belong.' She adds, 'Novelty is powerful. It lights up the brain and creates stronger memories.'
A survey by Original Travel shows that 62 per cent of parents consider their children's wants and needs more than their own when planning a family holiday. For teenagers, this is further complicated as often the last thing they want to do is hang out with their parents. King warns: 'Many parents hope for quality time, but for teens, being seen in public with their family can feel socially risky. It's not personal – it's developmental.'
With all this in mind, I set out to plan a trip with our three, confoundingly different, offspring.
As my husband was going to Milan for the weekend, I thought I could use this as a hook to put together a holiday, thinking breezily that entertaining the eldest two would be easy: they can explore Milan together. But as Mike Tyson said, 'Everyone has a plan until they get punched in the mouth.'
Eldest son tells me he will join us later in the trip. After some discussion, I made a holiday-planning WhatsApp group, asking for ideas and giving some suggestions. After a few days, only the eldest has responded, with his thoughts on the city break he's now not attending.
I turned to other parents. 'Italy is ideal,' one mother told me. 'It's safe, well-connected, easy on dietary requirements, and you can split up without anyone getting lost.' Thus validated, I pieced together a plan: start with three nights in Milan, head to Lake Como, then drive to Cervinia for skiing.
Milan is not front of mind for families, but it turned out to be a hit. Vintage shopping, a passion for my daughter, was an unexpected highlight. We began with high-end vintage boutiques run by flamboyant fashionistas on Via Gian Giacomo, and went on to more affordable second-hand stores around Corso di Porta Ticinese. We drank fresh juice and people-watched in the golden light.
The city's pace, lively but not frantic, suited us. Our rented flat was central, opposite the superb Gelato Fatto con Amore, and incredibly, on the same street as Leonardo's Last Supper. I failed to book the necessary three months ahead for Cenacolo Vinciano tickets, but it's free on the first Sunday of each month, for which tickets are only released the Wednesday prior, and, thrillingly, I managed to get us in.
To preserve the painting, only 40 visitors are permitted at a time, lending the moment a hushed and privileged reverence. We stood in front of the monumental painting, soothed by its golden-ratio proportions, and wondered at the way Da Vinci made the sky glow.
A short walk away, the Leonardo da Vinci National Museum of Science and Technology was more of a mixed bag. My youngest, art-loving teen enjoyed sketching Leonardo's anatomical drawings, while my son quickly decided he'd had enough and abandoned us to explore Milan on a Lime bike.
All of us, however, were awestruck at the ghostly beauty of the Duomo and the hallowed gilded high-fashion temple, Galleria Vittorio Emanuele II. I regretted not having made time to get to the Fondazione Prada with its Wes Anderson-designed bar (next time). We continued on to more success: a blow out, relaxed lunch at Il Cairoli, recently listed in the Michelin guide, where I ate saffron-golden osso buco risotto, and we enjoyed the unusual and lovely feeling of being together, with no particular plans, no rush.
The middle son's big ticket? San Siro with his Dad. The curvaceous 'Scala di Calcio' (opera house of football) has a different cadence of noise, smoke flares set off during the match, and seats 80,000. Middle son was suitably awestruck. 'It was so much louder, and the football felt different, more technical,' he explained.
Holidaying with teens? A doddle. We were clearly killing it.
But pride comes before a fall: in Como, an hour's drive from Milan, I'd booked a central Airbnb to allow easy exploration, which turned out to be a misstep. Piazza roadworks rattled our flat, and no one was interested in the Duomo view. A winding drive along the lake proved too much for my daughter, and a walk was quickly aborted. I should have let everyone rest for a bit, and I wished I'd booked somewhere in the countryside rather than thinking we needed to be in the thick of the (limited) action.
But Italy has a way of redeeming itself. That evening, we found an open-air restaurant screening an AC Milan game. We sat in the square eating pizza, enjoyed the fizzing excitement of the local supporters, with everyone relaxed and happy again. It might not have been my lakeside dream, but often, the simplest moments land best.
Leaving Como, we scooped the eldest from Milan's Malpensa airport, and drove 2.5 hours north to another world. Breuil-Cervinia has an altitude of 2,005m, and Europe's longest ski season, lasting from October to May, and year-round for advanced skiers on the glacier. We rented ski gear and spent a day with cheerful, skiing-before-they-could-walk instructors from Scuola di Sci del Cervino.
Our proficient sons took on the steeper routes, delighted to get the chance to ski over the Swiss border, while my husband, daughter and I skied the resort's broad blues that begin remarkably close to the great beak of the Matterhorn ('Cervinia' in Italy), with my daughter leading the way on every run. Fierce sunshine lit up the 'Meadow Horn' in all its jagged glory, and we zigzagged down and down again, insignificant specks against the sawtooth backdrop.
We skied all day, cooked delicious Italian produce, and visited the five-star Valtur Cervinia Spa, which we all loved, relaxing our ski-weary muscles, with plunge pool with jets, steam, saunas, and lots of entertaining novelties, such as a doccia scozzese ('Scottish shower') where jets were cold and from all sides.
Did the holiday work? There were a few wobbles en route, but there were also breakthroughs: big laughs, the shared wonder of seeing the Last Supper, then the quiet, snow-white brilliance of the Alps. When travel with teens works, it really works. Most importantly, though, this trip felt like a precious moment in time – like catching a butterfly on your hand before it flutters away.
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