We spent 15 days in Japan with our teens — here's why it's the ultimate family holiday
People in the streets of Omoide-Yokocho in Shinjuku Tokyo Japan
It's 9am and Tokyo is on fire. A heatwave has swept across the country, sending the mercury north of 36C by midday. Taking shade within Senso-ji, the city’s oldest Buddhist temple, we wait patiently to see what the future holds.
One by one, we drop a 100 yen coin into a slot, vigorously shaking a metal container, tilting it and pulling out a numbered stick. Turning to a wooden chest with numbered drawers, we open the ones that match ours, to withdraw a small piece of paper — our fortune, our omikuji. Handing each to our guide to translate, we learn our fate. Four of the five of them are bad.





Outside, a shiny new world greets us, all gleaming towers, pavilions, and open spaces pulsing with life. Before taking in the country’s third-largest city, we’ve come to say hello to a colleague from Mayo, who is here helming Japan’s first Waldorf Astoria. It’s a luxe layover on a family itinerary, and we drink in the views from our glamorous 36th floor bedrooms overlooking Osaka Bay and the far-off mountains. With a swimming pool on the 30th floor, Eggs Benedict with lobster for breakfast, and excellent sushi at the new Time Out Osaka market minutes away, we’re ready to take on Osaka.

Across town, OMO7 Osaka is in a grittier neighbourhood, and our giant family room is a lesson in fine Japanese design. The hotel’s ranger takes us on a walking tour downtown, revealing the sights before dropping us off for dinner in Jin, a traditional izakaya near the city’s iconic Tsutenkaku tower.


Along the way, we’ve learnt of emperors and ninjas, monks and Harajuku kids. There’s been monkeys and micro pigs, shrines and shopping. And there’s been so much laughter and learning. Ancient and futuristic, traditional and edgy, wild and regimented, Japan is more than we could have ever dreamed. Thinking back to our bad fortunes in the temple, we laugh. Could we be any luckier, we wonder, having the immense fortune of this unforgettable family adventure in the Land of the Rising Sun.
Where to stay
Hoshinoresorts.com/en/hotels/omo5tokyogotanda
Plan a Tokyo trip at GoTokyo.org
Plan a Kyoto stay at Kyoto.Travel
hilton.com/en/hotels/osawawa-waldorf-astoria-osaka
hoshinoresorts.com/en/hotels/omo7osaka
- Jillian’s trip was supported by GoTokyo.org, Kyoto.Travel, and Japan-experience.com, along with Hoshino Resorts, Preferred Hotels, and Waldorf Astoria.
