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Maui Recap: Travelling with Leo

Back in November, we went our VERY FIRST family vacation and since then many of you have been asking what it was like to travel with Leo, along with what I learned from our first trip together and what I brought with us and today I’m going to share some of this insight with you, in hopes that I can help some of the mamas out there who are about to take their first family vacation!!

Justin and I were so excited to take off to Hawaii and spend some time poolside and on the beach with our little Leo but I’m not going to lie, we were a LITTLE nervous for it as well!! I didn’t how he was going to handle the plane ride, and we don´t really like to have him in the sun for too long and I really struggled with what to pack. Next time we are going to rent one of the Visit Blue Mountain cottages to just relax out there with our little Leo and have some family fun.


Knotted Hat | Leo’s Shoes | Stroller | Nursing Pillow 

I was so nervous I was going to forget something that I ended up reaching out to Snuggle Bugz for some guidance!! As you already know, I love working and shopping with Snuggle Bugz (even more so now as they’ve gotten to know Leo and they also know exactly what stage he is at) … they are so accommodating and you can order everything online! I told them we were planning on going on our very first family vacation and I really wasn’t sure what I needed to bring and they ended up putting together a list for us with all of their suggestions which were so helpful! One of the many benefits of shopping at small, local businesses!! …

  1. Towel | 2. Swim Shirt | 3. Navy Reusable Swim Diaper  | 4. Red Stripe Reusable Swim Diaper | 5. Sunglasses | 6. Bucket Hat | 7. Baby Wrap | 8. Mineral Sunscreen Stick | 9. Natural Bug Spray | 10. Mineral Sunscreen Lotion | 11. Car Seat Travel Bag

As I was packing all of our stuff I was thinking that I probably packed too much … when we got to the airport and tried to maneuver all of our luggage I noticed that maybe I really did overpack … and now I can safely say that I really DID pack a lot and there were quite a few items I regretting taking along  with us but it’s hard when you feel like you need to bring everything “just in case”!!

I do however have a baby clothes packing HACK to share with you that I think you’ll appreciate just as much as I did … I absolutely LOVE using those little Ikea separator boxes to fold and store all of Leo’s little clothing … since it’s so small and awkwardly shaped it makes it easier to keep organized!!!! It was perfect to try out with the new baby boy clothes that I recently bought.

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Sunglasses | Swim Diaper | Sun Hat | Bathing Suit


Sunglasses | Bathing Suit | Bucket Hat


Bucket Hat | Leo’s Sunglasses | Ball Cap | Justin’s Sunglasses

We ended up bringing our own stroller and car seat along with us, these items are a MUST in my eyes … you can usually get a stroller and a car seat on for free on flights, so we thought why not bring them since we were checking them anyway?! We ended up using both of these items ALL the time and it was hassle free because we were already so familiar with how to use them!!

We also used Maui Baby Rentals for the items we didn’t bring along with us but that came in very handy … we got a bottle warmer, a bouncy seat, a cooler for the beach and a little beach tent!

jillian-harris-maui-hawaii-2Photo Credit

Sun Hat | Sun DressJillian’s Watch | Tote | StrollerBlanket | Justin’s Watch | Ball Cap | Sunglasses | Tee | Shorts

They have cribs and pack and plays in the hotels so there is no need to bring any of that with you (trust me, the less you can lug along with you, the better!!). One lady at the hotel brought a Dock a Tot but I don’t think that’s necessary, you can use two pillows to create a makeshift one that works just fine. Also, if your baby is 0-6 months you don’t need to haul any toys with you, in fact, babies this age need very little!!

I read a lot of comments and concerns about sunscreen and hats as well when I was sharing photos of our trip … and I have to admit that I have a bit of mom guilt here … I didn’t know you weren’t supposed to put sunscreen on kids until they reached 6 months and I totally put some on Leo (he was two months shy of the suggested age) … BUT in my defense, it WAS super simple and organic sunscreen!!

jillian-harris-maui-recap-travelling-with-leoPhoto Credit

Sun Dress | Watch


Ball Cap | Justin’s Sunglasses | Shorts | Leo’s Sunglasses | Swim Shirt | Swim Diaper


If I could leave you with a few pieces of advice, they would be …

1. Travel hands-free: This is a game changer. We ended up checking our stroller instead of taking it to the gate and I carried Leo around in his wrap, it makes the world of a difference when you are able to be with baby handsfree. I love the Solly Baby Wrap or the Beluga Baby Wrap.  Also! Bring a backpack to haul your necessities in, the Fawn Design backpack is a lifesaver … I didn’t have it in Maui but wish I did!!!

2. Nurse or feed on take off and landing: If you can do this, it will make your life (and your babe’s life) a WHOLE lot easier! If you can’t nurse or feed make sure to bring a soother!

3. Stick to your routine: This can be difficult while you’re away on vacation but trust me, the more you stick to the routine you’ve set back at home the better your trip will be for everyone! I recommend using a baby tracker app to help with this, I use Sprout! You can change your time zone to your typical time zone so you can track your babies sleep and eating schedule with your regular at home schedule, this is gold!

4. Simple is better: You may think you need to bring it ALL with you but trust me, the less you have to pack around the better and the worst case scenario … if you forget something, chances are you can buy it when you arrive at your destination!

5. Try not to stress: I know, this is easier said than done but honestly the more you learn to let go and relax the better your trip will be. Trust me, Justin and I had some tense moments but you have to learn to laugh things off and move on!


Shirt Maxi Dress

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Ball Cap | Tee | Watch | Sun Dress 

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What are some things you learned while travelling with your babe?!?! Make sure to share your stories and advice below in the comments section!! I also got some question about Immigration issues, to be honest I don’t really know much about the topic, but I know that the Reiss Edwards info provided by can help those who are looking for answer.

Happy travelling!!



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Leave a Reply

  1. Hi Jillian!

    My fiancé + our 6 year old son are actually going on a trip in April! So could definitely use these tips!

    I love your site and have been following you since the Bachelor! So happy you found Justin and now have Leo + Nacho! {We’re a Boxer family, too}
    They’re the best!

    Patiently waiting still for your engagement story! Hope it’s up soon!

    Take care!

  2. I am taking Connor, our 6 month old to the east coast in April to meet my side of the family, alone! Eeeek! I’m so nervous about how he will do on the plane, How did you keep Leo entertained on the flight? I’m worried that because it’s such a long day for us that Connor will get cranky on the flight. We have 2 layovers. I’m gate checking my car seat and stroller, so I can have them during the layovers, Connor never liked being carried. Hoping everything goes alright. Thanks for your advice, i totally downloaded the Sprout App just now!

  3. We just got back from Hawaii with our babe, great article. No guilt about the sunscreen! Our dr said it was fine to use on ours (4 months) Better than a burn!! My advice is get the best seats you can afford on the plane, so your little one isn’t kicking a stranger while feeding! We also booked flytographer and are so in ❤ with our photos!!!

  4. Love the tips! And advice you can share for the plane ride? Did Leo get fussy or cry on the plane and what did you do to soothe him? I was thinking of a trip to Hawaii when our baby is 8months but I fear the long haul. Would you suggest booking a flight with layover to give a bit of a break off the plane mid way?
    Also, what are the best seats to book, aside from first/biz class?

  5. Hi Jillian,

    Thanks for sharing your experience. Coincidentally, we’ll be taking our baby to Maui in a few weeks..he’ll be a bit over 3 months. It’s bitterly cold here in Toronto! Can you tell us:
    1) experience on the plane..anything you guys used to soothe..
    2) I’ve read about swimmer’s ear, bacteria in the ocean water..was wondering if you took any precautions when your little guy was in the water (ear plugs, ensuring head never submerged, etc).

  6. Hi Jillian! My husband and I are taking our baby, Kellan, who will be nine months old at the time to Maui! I just booked Flytographer as I saw your posts! Any recommendations on places to take baby? We plan on visiting the ocean centre but are unsure where else to go!

  7. Hi Jillian,
    Thanks for sharing your experience.

    How old were Leo when you first travel to Maui? Did he only drink milk? What are your suggestions for baby food in Maui?
    We are planning to go to Maui when with my 7 months baby…

    When you checked in your stroller & carseat, did you have to pay or they checked them for free? Which Airline did you travel with?
    Did you put your Bugaboo in Travel bag?

    Looking forward to hearing back from you.

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