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Written by Alison Smith

Hi! I’m Alison, and I recently travelled with my husband, our seven-month old daughter, and my parents, to Maui. My husband and I both love travelling as often and as far away as we can get, but we’re new to this whole “travelling with kids” gig. Maui appealed to us as it seemed to be the kind of place where we could do as much or as little as we wanted, and still leave feeling like we were able to fully experience it.

We opted to visit Maui in late September during shoulder season, as we wanted the best chance of rain-free days without having to miss out on decent weather in Calgary. The trade-off of travelling in September is that there are no direct flights from Calgary at that time of year (those usually start up in late October).

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Having never been to Maui before, let alone with a baby, choosing where to stay was daunting. We knew that with a seven-month old baby we would be spending more time at our accommodation then we usually do, so we opted for a self-catering condo in the small town of Wailea. What drew us to Wailea was that it’s known to be a bit quieter than west Maui, and is in close proximity to some amazing beaches along the south coast. We chose a place on Ulua beach and the Wailea Beach Path (we stayed at the Wailea Elua Village), which made it super easy to get out for a walk or a quick swim without having to pack for an apocalypse and load everybody into the car. Our condo had a stunning deck with an ocean view, and we spent a lot of our down-time there- having a coffee in the morning, reading on the lounge chairs in the afternoon, or watching the sunset with a glass of wine.

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We found that exploring the nearby beaches was the perfect morning activity for us (our baby never really seemed to adjust to Maui time, so our mornings started frighteningly early). This meant we often had the beach mostly to ourselves, and the water was calmer before the wind picked up in the afternoon. Mekena Beach (“Big Beach”) was our favourite- it was perfect to dip our baby’s toes in the water and watch the crashing waves, go for a long walk along the shore with her in the carrier, and relax in the shade. Our condo complex also had two great pools which we frequented most afternoons.

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Our daughter came along on most of our adventures, but for a few activities where bringing a baby was not an option, we “divided and conquer”- my husband and my dad went on a snorkelling trip to the nearby Molokini Crater one morning, and my mom and I went for massages at the Four Seasons spa another day. This allowed our baby to get in some decent naps, and for us to get in some grown-up activities. 

One of the major activities we did in Maui was drive the infamous Road to Hana. We debated long and hard about this, as it’s a long day in the car and we were not sure how our baby would handle it. In the end it turned out to be one of our favourite days. The whole point of the drive is to stop frequently and take in the sights along the way- which is ideal for a baby, as they never have to sit in the car seat for too long at a time. We were able to customize how we did the stops depending on what we needed at the time (quick stop to take a photo, or a longer stop to grab a picnic table and nurse/go for a walk while our baby napped in the carrier). We did a few things to prepare for the drive that worked well for us: we got an early start (6:30am), we packed a picnic lunch, we researched the stops ahead of time (so we knew which ones we absolutely did not want to miss), and we downloaded the “Shaka Guide” app (it uses your phone’s GPS to act as a tour guide for the drive so you don’t have to try and read from your phone or guidebook while driving the 600+ turns).  

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While we chose to buy groceries and self-cater most of our meals on this trip (there was an excellent Foodland just 10 minutes away in Kihei), we still managed to squeeze in some Hawaiian favourites along the way. A few highlights we indulged in: ice cream at Lappert’s (Kauai Pie for the win- coffee ice cream with coconut, dark chocolate, macadamia nuts and vanilla crunch); pineapple wine and charcuterie at Maui Wine; burgers at The Mill House restaurant on Maui’s Tropical Plantation; and banana bread at Aunty Sandy’s on the Road to Hana (every bit as delicious as the hype suggests).

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My favourite thing to do when I get home from a trip is go through all of our photos- in the moment sometimes things seem overshadowed by the chaos of it all, but looking back at it I realize all of the amazing memories that came out of the chaos. Travelling with our daughter allowed us to slow down and truly feel like we experienced the Aloha of the island.

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