When our son started elementary school, the long travel seasons disappeared and were replaced by short windows. That summer we picked one ambitious trip Wilder, then seven, would remember: Amsterdam, Singapore, Australia, and New Zealand. Four countries across three continents, squeezed into 19 days and made practical by careful routing and points.
Why we went when we did and how we booked it
We’d been to Australia before and wanted fresh places to explore; New Zealand felt like a natural add-on and Singapore made for an easy, interesting stop. Amsterdam began the trip because Ross already had work tickets there, and it proved to be a gentle, walkable start with plenty for a child. We used miles to upgrade long-haul flights to business class for the longest stretches, which let the three of us actually sleep on overnight segments. The flight pattern—New York to Amsterdam, Amsterdam to Singapore, Singapore to Australia, Australia to New Zealand, and Auckland back to New York—ran us about $5,100 after applying points and upgrades.
The route and highlights
Amsterdam was all about Wilder. A lifelong sports fan, he got to cheer at his first European football match—Ajax at Johan Cruijff Arena—which was electric. We mixed in quieter, kid-friendly activities: a canal boat ride, Dutch pancakes, and a family-focused visit to the Van Gogh Museum with a scavenger-style game that kept him engaged. We stayed at De L’Europe, which felt elegant without being stuffy.
Singapore was humid, colorful, and endlessly tasty. Wilder loved the inflatable HydroDash on Sentosa and the infinity pool at Marina Bay Sands. We arranged a visit to The Intan, a private museum of Peranakan culture, where Wilder tried painting tiles and sampled tea. Gardens by the Bay and accessible hotels helped smooth over jet lag.
Australia was the emotional heart of the trip. Based in Brisbane at The Calile, we visited Lone Pine Koala Sanctuary and even fed kangaroos. A day trip to Stradbroke Island with a Yura Bajara tour by Elisha Kissick combined storytelling with wildlife sightings—whales, a koala with a joey, and close-up kangaroos. On the Gold Coast we slowed our pace at the Mondrian: ocean views, a relaxed beach vibe, and a Jellurgal Little Explorers walk where Wilder learned to make paint from rock. At Spicers Hidden Vale we found rustic luxury; Ross went mountain biking while Wilder and I joined animal feedings and garden walks, and kangaroos wandered near our cabin.
In New Zealand we started in Auckland with the Sky Tower and the unexpectedly excellent All Blacks Experience, where Wilder even learned a bit of the haka. We drove north, visited Sheepworld for baby animals, and finished at Te Arai Links for surf, golf, and long barefoot walks along the coast.
Low points and how we handled them
Jet lag created some tough stretches: Wilder slept through a full lunch at Raffles, and on a Singapore food walk he nodded off in Ross’s arms. Mid-trip irritability from so much togetherness, plus mild colds for Ross and me, meant we needed to be intentional about giving each other space. Simple fixes—naps, ice cream stops, and small time-outs—kept tensions from escalating.
Unexpected wins
The glowworm experience in New Zealand became a quiet, unforgettable highlight. A tip from a local led us away from the crowded Waitomo tours to a family-run spot called the Milky Way Glow Worm Cave, where the owner guided us through a pitch-dark cave lit by tiny bioluminescent lights. It felt like stepping into another world.
In Singapore, the hotel arranged a visit to The Intan. Alvin Yapp welcomed us into his home, taught Wilder to paint a tile, served snacks and tea, and even played piano—an intimate cultural moment that felt more like being invited into someone’s living room than a museum tour.
Packing, logistics, and what worked
We traveled carry-on only—three bags for three people—using capsule wardrobes and planning two laundry stops. Traveling light made airport changes faster and removed the stress of delayed baggage. Upgrading long flights with miles made a big difference in energy levels on arrival.
What we learned
Family travel across continents rewards flexibility more than rigid schedules. Build in downtime and naps, be ready to pivot, and let kids help shape the itinerary. Adults travel better when they loosen control; many of the best moments were unplanned detours.
The bottom line
Group size: Two adults and one child
Days on the road: 19
Lodging: about $6,000
International flights after points: $5,136
Food, tips, extras: about $1,000
Total cost: about $12,136
We came home tired, sandy, and full of stories. Nineteen days across three continents gave Wilder another continent checked off his list and a trove of memories—football cheers, glowworm silence, kangaroo encounters, and first waves—that will last far longer than the jet lag.