It’s been almost three years since we went on our week-long trip to Maui with my side of the family to celebrate my sisters’ birthdays and parents’ wedding anniversary.

It’s taken me that long to decide on how to share our experience of traveling to Maui with a toddler, but we’re finally tackling it today!

First things first, this packing list is inspired by what I wore on the trip. The keyword there is inspired because if I’m honest, I way overpacked. I thought I would want options and daydreamed about shooting a ton of outfit content while on vacation, but the reality is I was in a swimsuit for most of the day, every day. I’m using my 20/20 hindsight to think about what I would pack if I was planning my trip for this year. My hope is that this post helps you keep it minimal and streamlined without sacrificing style.

But also, nobody is grading you on how well you pack, so use this as a jumping-off point if nothing else!

All right, let’s jump into the juicy details, namely:

what I packed for myself
a photo diary and overview of what we did

travel capsule wardrobe

These 22 items are perfectly mix-and-matchable for beach days, easy hikes, lounging at the pool, going out to eat, AND comfy enough for flying. The tops are all nursing-friendly. The dresses were a little more difficult to nurse in but I usually wore those to dinner so it wasn’t a problem.

smocked top | cotton tank | sleeveless top | gauze button-up shirt | cotton t-shirt

sweatshirt | midi dress | tiered cotton dress | sun dress | chore coat

denim shorts | linen shorts | light wash denim | linen blend pant

sunglasses | tie back swimsuit | one-piece swimsuit | high waisted bikini | packable hat

Teva sandals | woven mules | slide sandals

photo diary of what we did in maui

This was our first big vacation with a toddler and we learned a lot. Before becoming a parent, I was the type of traveler who wanted to pack every single day with multiple excursions so we could experience the place we were staying.

There’s a time and place for that kind of travel, but personally, I found that a gentle approach to vacation was what my toddler needed. We spent most of our days lounging around the pool at the resort, heading into Downtown Lahaina a few times and finding a couple of calm beaches to enjoy.

One thing we did that I wholeheartedly DO NOT think was worth it with a small child was the Road to Hana.

It’s basically a whole day of driving on winding roads. There are some beautiful hikes from what I’ve seen online, but they require more hiking gear than we owned and weren’t suited for our group of nature walkers and a newly-walking baby. Our poor kiddo was dry heaving in the backseat by the end of the day (I still feel terrible about it). More on that later.

day one

afternoon: We landed in the early afternoon and stopped by Da Kitchen (now unfortunately closed due to the pandemic) for a late lunch. Our hotel room had a full kitchen so we did some grocery shopping and cooked dinner at the hotel.

evening: Walked down to the beach to soak in the sunset! Izzy put his feet in the ocean for the first time!

day two

morning + afternoon: Enjoyed a birthday breakfast for my sisters (they’re not twins but they share a birthday) and spent the day at the pool. Izzy took to the water like a little fish.

evening: visited the Lahaina Historic District to walk by the beach and have dinner at Kimo’s Maui before heading back to the hotel to catch The Long Night episode of Game of Thrones.

day three

morning: paid a visit to the Aloha Ka Coffee Aka, the cutest little coffee bus nestled under some mango trees. The owner was there when we visited and was so cool. I had a field day snapping photos of her Volkswagon Bus turned coffee shop! I’m not sure if it’s opened back up post-pandemic, but if you get a chance to go, I recommend it!

afternoon: more pool time at the resort

evening: dinner at Nuka to celebrate my parents’ wedding anniversary (yep, we’ve got two birthdays and an anniversary back-to-back haha). The Pink Elephant cocktail was absolutely fabulous as was the sushi.

day four

morning + afternoon: headed to Kapalua Bay for a beach day. I snorkeled for the first time in my life (I know!!) and I loved it. I spent over an hour swimming in the bay, spotting fish and looking for a turtle. It was a highlight of the trip, honestly. Izzy also loved this beach! It was one of his first times seeing the ocean and he was thrilled. I like that this beach was in a bay because it made the water very calm and enjoyable for little ones.

evening: we ordered the most expensive pizza I’ve ever consumed from Round Table only to find out we could have ordered it from the resort for way less. 0/10 DO NOT recommend ordering pizza while in Maui. 😅 We finished off the day by catching another gorgeous Hawaiian sunset.

day five

morning: we set out for the Road to Hana. Like I said earlier, I would not do this again if we went back to Maui with small children. If you love road trips, your kids are older, and they love long drives, then go for it! There are some beautiful places to stop! I just can’t stress enough how boring this was for an almost-one-year-old.

We got coffee at Paia Bay, which was aesthetically nice but was very crowded and had just OK service. I would have liked to spend a little more time there exploring their breakfast/brunch menu, but we knew we had a looong day of driving ahead of us so we took everything to go.

We then stopped at Ho’Okipa Beach Park to see some sea turtles and we saw so many before hopping back in the car.

Our next stop was Twin Falls, where we traversed down a steep trail and across a creek to enjoy the view of the waterfalls. My sisters jumped into the water and Izzy explored alllll the rocks there. Brandon carried Izzy down (and back up) in his arms but if we were to do this again, I’d definitely get something like an Ergobaby carrier. We cooled off with some fresh popsicles made with sugar cane as the sticks before once again getting in the car.

afternoon: we weren’t able to stop at a few of our planned places because service is spotty on the drive and we missed a few turns, so we powered through and drove to Black Sand Beach in Hana and spent a couple of hours there. The walk down to the beach was beautiful but the waves were pretty intense for Izzy. The sand is more pebble than fine sand, but it was definitely worth the stop.

evening: we grabbed dinner at the 808 Plates food truck in Kahului. The food was DELICIOUS. I had the garlic shrimp plate and Brandon had the Korean chicken plate. I’d 100% make a trip to that food truck again.

day six

morning + afternoon: we were all exhausted so we relaxed at the resort for the day. I’m pretty sure we all just took turns napping!

evening: headed over to The Fish Market Maui and enjoyed some excellent fish tacos and seafood burritos.

day seven

morning: had a lovely breakfast at Betty’s Beach Cafe near the Whaler’s General Store. Having an early riser baby meant we were there before the rush and it was nice to have the place mostly to ourselves. We all ordered different things off the breakfast menu and were not disappointed. The service was really great, too.

afternoon: we spent the day out at Baby Beach, which is named appropriately. The water was so calm, it was truly perfect for a baby. It was raining when we got there but I’m so glad we stuck it out because we thoroughly enjoyed our time there. A sea turtle swam RIGHT IN FRONT of Brandon not once, but TWICE. It was magical. For late lunch, we headed back to the Lahaina Historic District and got some great food from the Lahaina Luna Cafe. We ended up throwing our Gathre mat down and hanging out in the grass with Izzy. He was just learning to walk on that trip so we gave him lots of space to practice and explore. We of course had to get some Dole Whip from Lappert’s Hawaii AND some shave ice from Ululani’s. I kicked myself for not going to Ululani’s every.single.day of the trip, it was that good.

evening: we made dinner at the hotel and packed to head home the next morning.

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I’m dreaming about the day we’ll be able to make the trip back to Hawai’i. I think next time we go, we’ll aim for the Big Island. Brandon and I honeymooned there and we really loved it!

Hawaii Packing List & Photo Diary