When our son started elementary school, the long open travel seasons vanished and were replaced by short windows—one week here, two weeks there. So that summer my husband Ross and I chose one big, ambitious trip that Wilder, then seven, could enjoy. He’d already been to five continents and wanted number six: Australia. We expanded that idea into a three-week route: Amsterdam, Singapore, Australia, and New Zealand—four countries across three continents—made possible by careful routing and points.
Why now and how we booked it
We’d been to Australia before and wanted new cities and landscapes. New Zealand felt like a natural addition, and convenient Singapore layovers turned into a full stop. Amsterdam was first because of pre-booked work tickets Ross had; it was easy, walkable, and kid-friendly. We used miles to upgrade long-haul flights to business class—Europe to Singapore and Auckland back to New York—so the three of us could sleep on the long flights. All flights for the family—New York–Amsterdam, Amsterdam–Singapore, Singapore–Australia, Australia–New Zealand, and Auckland–New York—cost about $5,100 after points and strategies.
The route and highlights
Amsterdam set the tone with Wilder’s interests front and center. He’s sports-obsessed, so we booked Ajax tickets; his first European football match at Johan Cruijff Arena was euphoric. We balanced that with a canal boat tour, pancakes at De Carrousel, and a visit to the Van Gogh Museum with a family treasure hunt that kept Wilder engaged. We stayed at De L’Europe Amsterdam, which felt elegant and warm.
Singapore was humid, colorful, and delicious. Wilder loved the HydroDash inflatable course on Sentosa, splashed in the infinity pool at Marina Bay Sands, and we toured Peranakan culture at The Intan, a private home museum. A street-food tour introduced us to chili crab and laksa while still finding kid-friendly snacks. Gardens by the Bay and polished hotels made it easy on a jet-lagged family.
Australia became the emotional center. We based ourselves in Brisbane at The Calile, feeding kangaroos and spotting platypuses at Lone Pine Koala Sanctuary. We ferried to Stradbroke Island for a Yura Bajara tour with Elisha Kissick, who combined storytelling with wildlife sightings—migrating whales, a koala with a joey, and kangaroos. On the Gold Coast, at the Mondrian, we slowed down: ocean views, Burleigh Pavilion, and a Jellurgal Little Explorers walk where Wilder learned to make paint from rock. At Spicers Hidden Vale, a rustic-luxury lodge, Ross mountain-biked while Wilder and I joined animal feedings and garden tours—kangaroos even roamed outside our cabin.
In New Zealand we started in Auckland: Sky Tower, the All Blacks Experience (surprisingly great), and dinner at Metita to celebrate Wilder’s sixth continent. Driving north, we stopped at Sheepworld for baby animals and ended at Te Arai Links, a coastal resort where we surfed, golfed, and walked barefoot between meals.
Low points
Jet lag produced some rough moments: Wilder once slept through an entire lunch at Raffles, and on a Singapore food tour he fell asleep in Ross’s arms in the heat. Mid-trip irritability from constant togetherness, plus head colds for Ross and me, meant we learned to be kinder, to give each other space, and to stop for ice cream when needed.
Unexpected wins
The glowworm moment in New Zealand became our emotional centerpiece. A Waitomo tour left me disappointed, but a tip at Bennett’s Chocolate led us to the family-run Milky Way Glow Worm Cave. On a whim we drove there; the owner agreed to lead us in. The cave was pitch-black and alive with bioluminescent “stars”—a private, magical experience Wilder quietly loved.
In Singapore, the Conrad Orchard arranged a visit to The Intan through a hotel program. Alvin Yapp welcomed us into his home, taught Wilder to paint traditional tiles, served snacks and tea, and played piano—an intimate cultural experience that felt like being invited into someone’s living room rather than a museum.
Matakana Village and Brick Bay in New Zealand were surprise highlights: artful public bathrooms that delighted Wilder, galleries, and a sculpture trail we did in the rain. The reflections and puddles made the art feel alive, and we finished with gelato.
Wilder’s favorites
We built the trip around Wilder’s interests. He still talks about cheering at Ajax, learning the haka at the All Blacks Experience, tackling HydroDash, and catching his first waves in New Zealand. Nature moments—feeding kangaroos, spotting a platypus, and making paint from beach sand—also stuck with him. Making him part of the itinerary changed the dynamic: he wasn’t just along for the ride; he helped shape it.
Packing and practicalities
We traveled carry-on only—three bags for three people—which was liberating. I created capsule wardrobes for each of us and planned around two laundry stops (Mondrian and Te Arai). Traveling light avoided baggage delays and made airport transitions smoother.
Lessons learned
Family travel across three continents requires elasticity more than efficiency: build in naps and downtime, be willing to pivot, and let kids feel seen. Adults travel better when they surrender a bit of control, and the best moments often come from detours.
The bottom line
Group size: Two adults and one child
Days on the road: 19
Cost of lodging: Approximately $6,000
International flights: $5,136 (offset with points)
Food, tips, extras: Approximately $1,000
Total cost: Approximately $12,136
We returned tired and sun-dazed but full of stories. Nineteen days, three continents, four countries—and for Wilder, one more continent checked off his list.