The highs and (deep dark) lows of travelling with two small kids

The following is excerpted from A Gelato A Day, a collection of family travel stories edited by Claudia Laroye © 2022. Reprinted by permission of the publisher, Guernica Editions. 

I’ve cage dived with crocodiles, hung off the side of holy mountains in China, and raced horses in Mongolia. But here’s the truth: The thought of travelling for the first time with my four-year-old daughter Raquel and nine-month-old son Galileo terrified me.

Curly-haired Raquel appears to have fallen Obelix-like into a cauldron of Red Bull. She’s a spirited T4 bull in the China shop of my tranquillity. With a head yet to discover the stars, Galileo is newly teething, crawling, and addicted to wrapping his gums and baby carrot fingers around any hazard he can find. Sure, Raquel had already been across Canada, Brazil and New York, but it’s different when they’re babies, too young to put spiders in their mouths. It’s different when there’s two of them.

The sooner my kids learn to travel, the better, and so I thought I’d start somewhere easy: direct flight, warm, and with a range of family-friendly accommodation options. I often tell friends that expectations are the death of successful travel. It’s no picnic on parenthood too. Before I got my hopes too high, it was important to acknowledge the facts: Children under the age of five are erratic, inefficient, agitated, annoying, moody, and masters of pushing buttons. Sure, you love them more than anything in the world, and there are moments of such tenderness, magic and wonder that you can’t imagine life without them. But whether we’re on the road or at home, no one can deny that we hard work for those moments, and pay for them in blood, sweat, tears, and dollars. Don’t let anyone tell you otherwise.

No matter how great your toddler vacation is, the reality is it will be bookended by a flight one building over and three levels up from Hell. As a travel writer, I fly a lot. It’s my chance to work, read, watch a movie, daydream at altitude. A six-hour flight from Vancouver to Maui should be nothing. If the kids sleep. Unfortunately, the only direct flight from Vancouver turned out to be a red eye. How bad could it be? Bad. Real bad.

Gali is licking tray tables and seatbelts. Raquel is having a full thermonuclear meltdown, vibrating with kicks and punches, and the plane is still at the gate. Rather than sleeping, they’re using the seats and occasionally other passengers as a trampoline. Playing Frozen on the iPad subdues Raquel for a while, but it only worked once, and then she just, well … let it go.

Like condemned prisoners at a public hanging, my wife and I gaze into the eyes of fellow parents, dealing with the trauma of their own journey. Each minute of each hour has the weight of a cannonball. Frazzled by the experience, I commit a cardinal travel sin and forget our two bottles of duty-free liquor—our blessed late-night boozy escape—on the plane. I hastily run back to retrieve them, but Air Canada’s cleaning staff relieved us of our bottles no more than five minutes after we had deplaned. “Sorry sir, our cleaners didn’t find anything,” the airline clerk says. Those fast-fingered cleaners must have young kids, too. I understand.

We grab our bags and shuttle to the car rental and spend the next forty-five minutes in a late-night line-up. Now the kids want to sleep. I push two chairs together and Raquel passes out. It’s these simple hacks that make one a Parent of the Year. I eventually get our van, install the car seats, strap in the kids, and load the luggage. It’s another forty-five-minute drive in the dark torrential rain to Wailea. Could anything be worth this?

Yes, waking up on the seventh floor in a Deluxe Ocean View suite at the Fairmont Kea Lani is definitely worth it. Sunlight sparkles off the Pacific below like a mirror-ball. Koi swim in ponds amidst manicured gardens and clear azure pools. Coconut trees rustle in warm tropical air with a fragrance sweet as nectar. Stripped of the jeans and hoodies we won’t touch for two weeks, our family hums with travel buzz. We’re chomping at the final bit of well-deserved beach vacation. When our feet touch the reddish sand of Polo Beach in triumph, it starts:

“I don’t want to go to the sea, Daddy!” “Gali is eating sand!” “It’s too hot, Daddy!” “It’s too cold, Daddy!” “I’m hungry!” “I’m not hungry!” “Where’s my blue spade?” “I want a red spade!” “I want what that other girl has!” “Pick me up!” “Put me down!” “This rock is scary!” “I want to go to the pool!”

Toddlers are complex algorithms dancing to a convoluted rhythm only they can hear. The first chance my wife and I get to relax is much later that night when both kids are asleep. No late-night walks on the beach for us, but we do sip cocktails on our lanai, beneath a planetarium of stars, the scene scored by the soporific sound of crashing waves. The flight is a distant memory. Aloha Maui. Finally, aloha.

Buffet breakfasts have ruined us. Raquel quickly gets used to having one mouthful of a dozen different dishes, and miso soup is now a breakfast staple. My wife and I tag team feeding both kids as Gali singlehandedly supports the birdlife of Hawaii gathering beneath our outdoor table to feed the snow of egg that falls from his highchair. Staff give us crayons for the kids each morning, and despite the buffet, Gali’s favourite breakfast dish is Crayola Red.

Hours turn to days as we rotate between the pool, suite and beach. Raquel is too young for Kea Lani’s Keiki Kids Club, but she can drop into its day-care-like facilities in the afternoon, when Gali is napping in the room and the sun is too strong. There were so many toys about I almost cried when we enter for the first time. Finally, she’ll be happy, contained and entertained without me! Later, we explore the grounds, make a run to the nearest supermarket, and buy a few things we didn’t pack while realizing we don’t need most of the things we did. Later, the family dines at the sensational restaurant downstairs, a romantic meal of dreams invaded by our overtired, over-hungry kids who care little for the chef ’s inspired creations. Before the appies arrive, out come the apps. I survey the restaurant for looks of disapproval, but nobody makes eye contact, probably because they’re afraid I’ll ask them to look after the kids while I get a bite in. My wife turns to me and says: “Please don’t go to the bathroom. I’m afraid you might run away.”

Every time I meet a Dad or Mom in the knee high, pee-warm toddler pool where the kids spend most of their time (sandy beaches be damned), we share 1,000-yard stares, shrug our shoulders, and let the giggles and laughs of our kids melt our hearts. As with parenthood, it’s so much easier to identify and share the challenges as opposed to the indescribable joys. There is an Adults Only section at the Kea Lani, and I wonder how many hearts are melting in it like ice in umbrella-topped cocktails. Travelling with young kids and travelling as adults would be comparing apples to oranges, both of which I recommend taking from the buffet in the morning because fruit comes in handy later for snacks.

Fairmont’s luxurious resort was our high-end splurge, a refuge of stunning views that fluffed our eyes like pillows at turn down service. It is the other end of cheap. On our final morning, Galileo stands up in his hotel crib beaming his two-tooth smile and says “Dadda” for the first time. I pick him up, step out onto the balcony, and together we admire the postcard view before us. Cost of that moment: Priceless.

We’re relaxed. We’re finally in the flow, and on a schedule that works for the kids. Everything is great. Now let’s dynamite that magic to hell. Air Canada’s return flight from Maui is a red eye. (They don’t call it Air Canada Rouge service for nothing.) We arrived at the airport two hours early and barely made check-in. Line-ups, heat, frustration, delays, wrong seat assignments—every hour that dripped by eroded the pleasant memories of Maui.

Once on the plane, the kids become caged monkeys, eventually collapsing in exhaustion on the unspoken condition that their parents would not. Ana bends herself into a pretzel on the floor with one kid using her as a pillow and the other as a footrest. Raquel has another epic meltdown on arrival, and by the time we get home, she climbs on the couch, puts a blanket over her head, and we don’t hear from her for six hours. She’s never done this before, and we really hope it’s the start of a trend.

A few days later, the colours and tans of Maui are fading, but our experiences on the island remain bright, our photographs sealing in memories with a varnish that will only improve and become more valuable with time. I pick up Raquel from daycare, and ask her: “Did you tell everyone about Maui?”

“No,” she replies. “I forgot to.”

Toddlers.

She might be over it, but I’m hopeful our two weeks on the Valley Isle hardcoded our children with a love for the ocean, island life, the aloha spirit of Hawaii, and an appreciation for warm, sincere hospitality. It definitely hard-coded a love for travel, for the next sentence out of Raquel’s mouth is: “Where are we going next?”

Robin Esrock is the bestselling author of The Great Canadian Bucket List and The Great Global Bucket List. Inspired by their experiences in Maui, the Esrocks decided to spend 12 months travelling in Australia and Southeast Asia.