For more than a decade Whitney Spielfogel’s family has kept a ritual: an annual, multi-generational getaway with her parents, her husband Ross, and eventually her children, Sienna and Slade. These trips — past destinations including Hawaii, Costa Rica, Cabo, Tulum and Turks and Caicos — were a way to pause everyday life and be fully present together. After her father, Papa Norm, the family florist who brightened every room, died unexpectedly, the tradition continued in his honor and became bolder each year. This time they went farther than ever: Thailand.
Their itinerary was deliberate. They flew from New York to Bangkok via Istanbul, spent a busy day exploring Bangkok, then three nights in Chiang Mai (staying at the Aleenta), nine nights at COMO Point Yamu in Phuket, and a final night at the Rosewood Bangkok before the long flight home. The three-stop plan had a purpose: dive in immediately, move into culture and nature, then finish slowly with sun and stillness. They avoided rental cars and relied on hotel concierges, short domestic flights, and local drivers to keep the trip smooth and low stress.
Whitney’s travel strategy was simple: start strong while energy is high, then decelerate. Their first full day included temples, canals, tuk-tuks, and a bustling flower market — a particularly poignant stop given Papa Norm’s career as a florist. Instead of racing to check boxes, they aimed for emotional entry points. A river boat ride with golden temples on the horizon and two wide-eyed kids became one of the trip’s most treasured moments. When their luggage didn’t arrive with their flight, attentive hotel staff shopped for essentials and managed a seamless transfer days later, turning a stressful moment into a little adventure.
The trip favored experiences that invited everyone to participate rather than nonstop sightseeing. Hands-on activities translated across generations. The elephant sanctuary in Chiang Mai was the emotional centerpiece: feeding elephants, preparing food, giving mud baths and splashing in the river together created a ‘‘pinch-me’’ family memory — children, mother, and husband in the water at once. A cooking class at the Aleenta and market explorations made Thai cuisine tangible for Sienna and Slade; rolling spring rolls and making pad Thai helped the kids embrace the food instead of avoiding it.
After several active days, Whitney built in restorative time. The Phuket stretch settled into a relaxed rhythm of morning swims, boat outings, slow afternoons and long meals. Evenings often ended with Uno, a nightly ritual that connected generations and neighboring families so reliably they joked their travels were sponsored by Uno. Staying long enough in one place to feel grounded, rather than merely passing through, transformed the vacation. Celebrating New Year’s Eve in one hotel reinforced a sense of belonging and made the transition into a new year feel both joyful and communal.
Some of the most meaningful moments were quiet: watching Whitney’s mother share firsts with her grandchildren, whether a cooking triumph or an encounter with wildlife. Small rituals mattered — slow breakfasts, lingering dinners, letting kids nap where they would so the group could stay together. They added a boat day in memory of Papa Norm, which gave the trip extra emotional weight beyond the itinerary.
Practical details that helped: both kids carried Polaroid cameras, continuing a family tradition of snapshot souvenirs; slip-on shoes made temple visits easier; sunscreen was essential for southern heat; and the Uno deck never left the bag. Those small items made travel easier, helped the children adapt to time changes, and kept curiosity alive.
Whitney’s advice for families considering multi-generational travel: phase the trip — put high-energy sightseeing at the start, save restorative time for the end, and leave space for the unexpected. Build true downtime and acknowledge different recharge styles; let children have input in the day’s rhythm; plan thoughtfully but keep room for spontaneity. Above all, prioritize shared activities that invite participation. Big, noisy moments and quiet, ordinary minutes together are what turn a trip into a lasting family story.
