When Fiona Ching decided to plan a multigenerational family holiday in Hokkaido, Japan, she braced herself for a logistical challenge. Coordinating a trip for ten people spanning various ages and interests—ranging from her seven-year-old nephew to her 75-year-old father—was no small feat. But surprisingly, the trip unfolded with far less stress and far more enjoyment than anticipated.
Ching had spent several months traveling in Japan with her partner, Cameron, and invited her extended family to join them in Otaru, a charming port city on Hokkaido’s west coast. The family, eager to explore the island, quickly booked their tickets, and Ching found herself faced with the task of creating an itinerary that would cater to everyone’s needs.
“I needed a van with a driver, spacious hotels, group-friendly restaurants, and hiking spots for seniors,” she recalls, navigating through a whirlwind of planning. Her biggest challenge was balancing the diverse needs of the group. How could she entertain an energetic child, accommodate senior citizens, and give her shopping-enthusiastic aunts enough retail therapy—all while keeping the pace comfortable?
Despite her meticulous planning, Ching quickly realized that her family was simply happy to be together and explore a new destination. Their first day in Otaru was easy-going: after settling into a traditional ryokan with tatami rooms, they ventured to a nearby sushi restaurant, where the hustle and bustle of Cantonese chatter filled the air. The experience was a reminder that family togetherness mattered more than flawless execution.
The following days saw the family exploring the picturesque streets and canals of Otaru, a city rich in history and iconic architecture. As they strolled past 19th-century bank buildings now converted into museums and shops, the family indulged in another Hokkaido specialty: ice cream. From vanilla to more adventurous flavors like uni (sea urchin), the ice cream quickly became a highlight for the entire group.
The true magic of the trip, however, came from the moments of serendipity. A planned visit to Cape Kamui, a scenic promontory, turned into a memorable adventure when the aunties decided to join the younger family members on a giant roller slide—a moment of shared laughter that was as delightful as it was unexpected.
The family continued their journey into Hokkaido’s interior, where they visited the Asahiyama Zoo, home to polar bears, penguins, and giraffes, before heading to Daisetsuzan National Park. The gentle cable car ride up Mount Asahi, Japan’s tallest peak, provided panoramic views of the mountains, with family members of all ages enjoying short hikes through trails that led to steaming sulfur vents.
A stay at the Oyado Shikishima Sou ryokan in Tenjinkyo Onsen provided an additional test of the family’s comfort zones. While some of the aunties initially hesitated at the prospect of communal onsen baths, they eventually embraced the experience, with even the children enjoying multiple soaks in the hot mineral waters.
Furano, known for its fragrant lavender fields, marked the final leg of the trip before reaching Sapporo, Hokkaido’s largest city. It was here that Ching observed the family’s growing confidence as independent travelers. In a ramen alley in Sapporo, the aunties took charge, directing the family to different restaurants and ordering on their own—navigating menus with the help of Google Translate.
By the end of the trip, Ching realized that her carefully planned itinerary had been just a backdrop to what truly made the holiday special: the simple joy of spending quality time together as a family. What started as a stressful task of balancing interests and comfort zones ended in an unforgettable journey, with the family already discussing future adventures.
As Ching sums up her experience, “It wasn’t about perfect planning, it was about enjoying the moments we shared together.”
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