For the past decade Whitney Spielfogel’s family has taken a multi-generational holiday trip with her parents, husband Ross, and eventually her children, Sienna and Slade. These seasonal getaways—Hawaii, Costa Rica, Cabo, Tulum, Turks and Caicos—were their way of pausing ordinary life to be fully present together. A few years ago, her father—Papa Norm, the family florist who charmed every room—died unexpectedly. The tradition continued in his honor, growing bolder each year. This time they chose Thailand, their furthest adventure yet, with Whitney, Ross, Helen (known as Lala), eight-year-old Sienna, and five-year-old Slade.
Their route: fly from New York to Bangkok via Istanbul, spend a packed day in Bangkok, then three nights in Chiang Mai at the Aleenta, nine nights at COMO Point Yamu in Phuket, and a final night at the Rosewood in Bangkok before the long flight home. The three-stop plan was deliberate: begin with immersion, move into culture and nature, then finish with stillness and sun. They skipped rental cars and relied on hotel concierges, short flights, and local drivers to keep the trip fluid and low-stress.
Whitney’s strategy: start strong while everyone still has adrenaline, then slow down. On their first full day they hit temples, canals, tuk-tuks, and a bustling flower market—a poignant stop given her father’s career. Rather than ticking boxes, the goal was an emotional entry point: a river boat ride with golden temples in the distance and two mesmerized kids became one of their most grateful moments. Choosing accommodations that provided calm after travel mattered: when their luggage didn’t arrive, attentive hotel staff helped shop for essentials and ensured a seamless transfer days later.
Her biggest tip for multi-generational travel is to choose experiences over endless sightseeing. Hands-on activities that invite participation were far more meaningful across three generations. The elephant sanctuary in Chiang Mai served as the emotional centerpiece: they fed elephants, prepared food, gave mud baths, and splashed in the river together. Whitney describes the family in the water—kids, her mother, and her husband—as a “pinch-me” moment and a lasting core memory.
They balanced that with a cooking class at the Aleenta and market explorations. Preparing pad Thai and spring rolls made the culture tangible for the children, who embraced the food instead of shying away. Whitney’s takeaway: when children are included and active, they engage naturally.
After days of movement, Whitney designed the final stretch for rest and rhythm. Days at the Phuket hotel settled into morning swims, boat outings, unhurried afternoons, and long meals. Evenings often ended with Uno, a nightly ritual that connected generations and other families—so much so that they joke their travels are sponsored by Uno. Staying long enough to feel grounded rather than transient transformed the trip. Celebrating New Year’s Eve in one place reinforced belonging and marked a joyful transition into the new year.
Whitney says the most meaningful moments were often the quiet ones: watching her mother share firsts with her grandchildren, from cooking to wildlife encounters. She encourages families to protect simple rituals—slow breakfasts, lingering dinners, and letting kids nap where they will so the group can remain together. Incorporating a boat day in memory of her father added deep meaning beyond the itinerary.
Practical notes: both kids carried Polaroid cameras, continuing a family tradition of snapshot souvenirs from trips past. Slip-on shoes made temple visits easier, sunscreen was essential for southern sun, and the Uno deck never left the bag. Those small items helped the kids travel well—adjusting to time zones, keeping pace on busy days, and absorbing the experience with curiosity.
For families considering multi-generational travel, Whitney suggests phasing the trip: load high-energy sightseeing at the start, save restorative time for the end, and leave space for the unexpected. When their luggage delay forced a concierge-led shopping trip, flexibility turned stress into a memorable, funny moment. She also recommends acknowledging different recharge styles—build in true downtime, let children have some say in the day’s rhythm, plan thoughtfully, and leave room for spontaneity. Above all, enjoy the big and small moments together; they’re what make a trip unforgettable.
