It was four hours into a six-hour flight to Maui when I heard a soft chirp from the seat behind me. I looked back, and to my surprise there was an itsy-bitsy baby cuddled up in his mother’s arms. The junior jet-setter was a mere 6 weeks old. 

At the time, circa 2005, I was nowhere near the mother stage in life, but the scene stood out to me. First, I was impressed with the couple’s tenacity traveling with an infant. Second, I was so inspired, I decided that when Mr. Trip Styler and I brought a wee wanderer into the world, we would take him to The Valley Isle in his first year of life.

Fast-forward 10 years.

In late 2014, our little one burst into our lives on “Island time” (read: He was 11 days late), and, amid our busy intro to parenthood, my mind escaped to the exotic. I was determined to follow in the footsteps of that couple behind us on the plane 10 years earlier and take our little munchkin to Maui. 

After 15 trips to the Hawaiian Islands, I get it. Now I know why Maui is held in such high parental esteem. It’s tropical (read: You don’t have to lug a ton of clothes). Locals are lovely. The culture is family-focused. Diapers and wipes are always nearby. I could go on. In short, it’s easy-breezy for a brood trying to figure out life (and travel) together. Put differently, Maui is a great place to take a little one.


Our brood in Maui


Hotel life

While some families opt for a life-long prescription of vacation rental properties once they start traveling with their tykes, we took the opposite approach, and made a hot dash for hotel life.

We wanted a vacation rather than a kitchen, and a styled stay without toting a bunch of stuff. (I’m pretty minimalist, but, the stuff required for upwardly mobile babies blows my mind).

Viewfinder Tip: When traveling with a baby to Maui, bring a two-day starter kit of diapers and wipes, then buy the bulk of your supplies on the island.

“Would you like a bottle warmer, potty, playpen, wipes, change table, high chair, rocking chair, baby walker, etc…“ the Four Seasons Resort Maui at Wailea‘s housekeeping department asked when I called to ask about an extra baby blanket. Then came my awkward pause. I was so shocked by the 30-or-so baby items my guardian housekeeper rattled off, I could barely respond.

“Oh, just a walker, a-a-and the blanket would be lovely, thank you,” I said. 

Of the almost 20 hotel stays we’ve done with our now 7-month-old, we’ve never had that level of choice or selection. Even our electrical outlets were child-proofed in advance, there was a Diaper Genie waiting for us, and when we walked into the bathroom, we found a collection of sponges spelling our son’s name. (For the record, I travel once every two weeks and I’ve never walked had my name spelled in sponges!)


Baby playpen in our cabana (bottom left) at Four Seasons Resort Maui at Wailea

Pool life was no exception, either. I’ve learned that in heat and all-day sun, consistent shade is my BFF when traveling with a baby. And while most resorts on the island charge an extra fee for shaded cabanas, these are included at the Four Seasons (and so is the playpen the pool staff placed between our two lounges so our peanut could savor the pool scene with us). 

Nights out (with baby)

As much as Maui is family-oriented with its steady flow of family pools and day-centric culture, our night-time plans were my biggest concern. We still wanted a semblance of sunset romance, and the thought of being sequestered to our room every evening at 6:30 p.m. for baby bedtime was a no-go. 

On a few low-key nights, we walked to the local buy-anything-you-can-think-of shop, aptly named, ABC Stores, to grab a salad and ice cream to-go. Most of the time, however, we embraced hotel happy hours, which OFTEN allow kids. This is where we felt like we were winning at the game of kid-in-tow travel. No, we didn’t bring a babysitter or grandparents or a nanny so we could stay out until dawn, but, yes, we could still sip a cocktail carved into a pineapple at sundown.

Tuckered from his days, our little guy dozed off in his stroller next to us as we ordered additional rounds. I silently dedicated each of these rounds to that couple on the plane all those years ago. If they hadn’t had the gumption to glide across the Pacific Ocean with their bundle, I’m not sure I would have been sitting in high heels soaking up island life. I just hope nobody noticed the splatter of spit-up on my dress.

What are your tips for traveling with a baby?