For the past decade, Whitney Spielfogel’s family has taken an annual multi-generational trip over the holiday season and New Year’s with her parents. Hawaii, Costa Rica, Cabo, Tulum, Turks and Caicos. They had done them all together, her parents and her husband, Ross, and eventually her children, Sienna and Slade. The trips were their way of pressing pause on the ordinary world and being fully present with each other. “We always take these trips over the festive season and New Year’s so that we have an extended time to go away, be present, and truly shut off, unwind, and enjoy one another’s company,” Whitney says. Then, a few years ago, her father—Papa Norm, the family florist, the witty one who charmed every room he walked into—died unexpectedly.
However, the trips continued in his honor, growing bolder each year. Belize. Honduras. And this year, something none of them had quite attempted before: Thailand. “This was our furthest adventure together yet,” Whitney says. She traveled with her husband, her mother Helen (known to the grandkids as Lala), Sienna, who is eight, and Slade, who just turned five and has now hit five continents. “And of course,” Whitney adds, “all the adults had watched The White Lotus.”
This year’s journey would be their most ambitious yet, and their first to Southeast Asia.
The Route
The family flew from New York to Bangkok, via a stop in Istanbul, Turkey (Editor’s note: The trip described here took place prior to the Iran conflict), and spent one packed day adjusting to the city’s rhythm, before continuing north for three nights in Chiang Mai, staying at the Aleenta, before heading south for nine nights at the Como in Phuket. A final night back in Bangkok, where they stayed at the Rosewood, provided a soft landing before the 22-hour journey home—strategically timed to arrive on a Friday, giving everyone the weekend to recalibrate.
The three-stop structure was intentional: Start with immersion, move into culture and nature, then finish with stillness and sun. They skipped rental cars entirely, relying on hotel concierges, small flights and local drivers, a decision Whitney credits with keeping the trip fluid and low-stress.
Start Strong, then Slow Down
Whitney recommends using the first full day to absorb the energy of a new place while everyone is still running on adrenaline. Her family scheduled their most ambitious sightseeing early, temples, canals, tuk-tuks, and a bustling flower market that held special meaning given her father’s career as a florist. But the goal, she says, isn’t to check boxes. It’s to create an emotional entry point. Taking a boat along the river, with golden temples in the distance, and the children completely mesmerized, became that moment. “It was one of those travel moments where you just feel incredibly grateful to be there together,” she says.
