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12 Frequently Asked Questions about My Hawaiian Vacation

Aloha!!! Whenever I travel, I tend to get a ton of questions coming in on my social platforms so I thought I would round up a few questions that were most frequently asked and answer them here! PLUS, I took so many videos while we were in Hawaii that I also decided to share a vlog with you too!!

Are you ready??

1. Do you prefer Hawaii over Mexico?

When it comes down to choosing my favourite tropical destination, I have to go with HAWAII!! Hawaii is one of my first best memories, I went when I was 5, again at 8 and I’ve been in love since! I do prefer Hawaii over Mexico mostly due to the fact that I feel safer in Hawaii and it’s so familiar. There has been a lot in the news lately about Mexico and safety concerns, so when it comes to a trip with my little family I like to stick to Hawaii. I’m SURE Mexico is fine and safe but you asked my opinion and that’s how I feel LOL!!  Now, don’t get me wrong, if I want to escape for a quick girls trip, I would totally consider going to Mexico, it’s also much more affordable and a little more “fun” … Hawaii has pretty much zero nightlife (at least Maui anyway).

I also like the fact that Maui doesn’t seem as touristy … even though parts of it is, I feel as though the island is big enough that you can really blend in with the locals and find your favourite hole in the wall joints.

Jillian Harris Hawaii QA

2. Where is Annie’s yellow swimsuit from?

I SWEAR she likes it!!! LOL! Annie’s yellow swimsuit is from Hannah Anderson (you can find it here!) and the matching suits Annie and I have are from Imagine Perry! You can also find crazy cute swimsuits from GAP (like the red one below!!), Old NavySwim Zip, and Honeysuckle Swimco!

Jillian Harris Hawaii QA

3. How was Leo with potty training on the flight?

If I could sum it up in one word, it would be: horrible! LOL! Somehow along the way, Leo came up with the idea that public bathrooms are dirty and he refuses to go pee or poop in them! Even at the Fairmont, one of their bathrooms is painted a rich brown and he wouldn’t go to the bathroom in it because he thought the walls were covered in poop! LOL!

Before we left for our trip Leo stopped using diapers and pull-ups (LIKE REFUSED to wear them) soooo when we were flying it took about 5 trips to the bathroom to convince him to actually GO so he didn’t pee his pants! Since that experience, we have got him BACK on the pullup train and he is back to wearing them at night and long trips since we haven’t had the balls to convert his crib to a big boy bed!!

Jillian Harris Hawaii Recap

4. What was your vacation like with a toddler and a baby? What did you do?

Well, folks, it is not the same as the good old days. GET YOUR SLEEP WHILE YOU CAN PEOPLE!!!! It’s the little things you have to constantly think about that keeps you running just as busy as you were at home!! Keeping them out of the sun, making sure they are covered in sunscreen, have enough food, drinking enough water, nap time, sand in eyes, where is your other sandal, no don’t go over there!, don’t eat THAT … omg! Yes, nap time, wait don’t fall asleep NOW!??! LOL! If you’re a parent I think you know the drill. And then you order a Mai Tai thinking that will solve your problems but it only makes it worse! LOL!!

What about the time when Justin warned me that Annie was going to get sand in her face if I laid her on a towel at the beach, I ignored him and she LITERALLY got an EYEFUL of sand?? Ummm ya, okay, so I wasn’t exactly relaxed on this trip.

But I’m not complaining, we had an AMAZING time and made wonderful memories … it’s just travelling with kids, you most definitely have to adjust your expectations.

So, here’s what made it a bit easier for us which is not always going to be possible because financially it’s a bit of a stretch to travel like this every time. We had a 2 bedroom villa at the hotel (Fairmont Kea Lani) which just happens to have a big patio, is on the beach AND has its own little pool. Now that I know what its like, and I’ve been spoiled, I’m never staying in a regular hotel room again for this kind of vacation. IF these villas are in your price range I would HIGHLY recommend them. They have a big kitchen, you can lay the kids down for naps and still enjoy the sun … there’s room for everyone and you don’t have to travel to get to the beach. If we can’t afford the villa, then I think we will do an Airbnb! We can get back to “regular” rooms when the kids are older, not napping, and easier to get around. Another option would be to go with another family and split it as we only really USED the one bedroom!!

Anyway, with the villa, we hung out a lot right at “home” Leo was able to build sand castles with Justin just a few steps away and work on his golf swing on the lawn.

When we were at the pool we made sure to rent a cabana, if you don’t have the option to snag one on your next trip, I would totally recommend getting an umbrella, or make sure to bring your own if you can! They are a necessity to have on hand to keep the babies out of the sun! If you’re in Maui, there is a company called Maui Baby rentals where you can rent all sorts of things like coolers, baby chairs, umbrella’s, strollers, etc! This is perfect if you don’t want to haul a bunch of stuff with you while travelling!

We also brought our Bugaboo Bee for Annie (I transferred her out of the bassinette at 3 months, and she sits up just fine in a regular stroller) and we also brought along the Bugaboo comfort wheeled board for Leo and he LOVED riding around on it, it was SUCH a lifesaver for us! We brought our stroller everywhere with us, we would even drag it out onto the beach as it has a sun canopy on it which provides great sun coverage for Annie and it’s also breezy!!

We went on LOTS of walks, got in some a little beach time, played mini golf, spent time in the pool, and got room service! We didn’t leave the resort really at all this time except for mini golf as everything we wanted and needed was there!! Like I said, if you are doing it with kids this age, (under 1 and 2.5 years) I would highly recommend a place with a kitchenette or getting an Airbnb with a pool / close to the beach and a covered area!

Jillian Harris Hawaii Recap

5. Must see things to do?

Well, the last few times I’ve been to Maui I have just soaked up the sun and enjoyed some much needed R&R but I’ve definitely blogged about some of my favourite things to do from my prior trips! If you want to take a look and read up on all of my Maui recaps, take a look at all of the different blogs FILLED with info HERE!!  I would say though I don’t overdo it these days. I’m so busy at home that when we are in Maui I really try to CHILL and just take it easy.

Jillian Harris Hawaii Recap

6. What are some of your favourite eats?

I LOVE this question!! I shared a detailed list of my ALL-TIME favourites places to eat, here! However, I’ll share a few of them below for quick reference!

The Fairmont Brunch (I love their Tofu scramble!)

The Five Palms Breakfast (The omelet here is amazing, but you go here for the view! They also have a good Happy Hour every night!)

Joy’s Kitchen (Delicious vegetarian and vegan options!)

Leoda’s Kitchen & Pie Shop (They have unreal pies!)

Choice’s Kitchen (Insanely good smoothies and Acai bowls)

Hawaiian Moons Grocery Store (Tons of good vegan food and smoothies!)

Monkeypod (LOVE their mushroom dumplings and they have the BEST Mai Tai’s!)

Maui Tacos (Delish fish bowls and it’s inexpensive!)

Jillian Harris Hawaii Recap

7. What are the sleeping arrangements when you travel with Annie & Leo?

This is another tricky one when travelling with little ones who are still napping. So here’s my trick … normally when we go on vacations I try to find a room that has either a suite (1 bedroom with a door) or I ask if they have a big walk-in closet, or a second bathroom (sorry Leo) … basically ANYWHERE I can put 1 child down for a nap or to bed, and we can still be in the room and don’t have to all go to bed at 7:30 or tiptoe around during nap times!

My kids (well Leo anyway) isn’t one to just sleep wherever. I’m not sure if it’s just who he is or if sleep training ruined him but he will only nap in a quiet dark place (or in the car). Lately, we like to splurge and stay in either a villa, a suite or get an Airbnb … because it allows for a little more space and napping opportunities!

Right now, with Annie being less than 6 months I actually find an ottoman, a few chairs or something I can push up against the bed, and I put the dock a tot on it, or the dock a tot will go on the bed with us. Once she gets a bit older and they BOTH need a crib and they are BOTH napping … I don’t know what I’ll do. We might have to stop vacationing if we need to get a 3 bedroom accommodation!!! LOL!!

Jillian Harris Hawaii Recap

8. Where do you love staying when you’re in Hawaii?

I love staying at The Fairmont Kea Lani (in Maui!) … we’ve been EVERY YEAR for 6 years and now I feel like it’s mine and Justin’s special little place! I was saying to Justin this last time that I’d LOVE to be able to bring the kids there for years to come. On the big island we love The Fairmont Orchid, and in Waikiki, I’ve stayed at The Moana Surfrider, and The Royal Hawaiian (which is great for pics!). But, I’ve never been to any Waikiki hotels with kids so I can’t help you out there!

There are some INCREDIBLE Airbnb’s in Hawaii which we normally stay at when we travel with Justin’s parents! There’s  my old condo, yes, it’s STILL available to rent even though we don’t own it anymore! Jenna Kutcher’s place, The  Kutcher condo it’s STUNNING and so is Yuriko’s Hawaiian escape!!

Jillian Harris Hawaii Recap

9. Do you use your iPhone to capture your photos when you’re in Hawaii?

Yes!! I stopped bringing my DSLR with me a long time ago as it’s just too much to pack around and I would probably end up getting sand in my lens or something!! I love how handy taking photos on my phone is!! Plus, now that my presets are launched it will now be super easy for YOU to get the same look on your photos that I use on mine! We also use Flytographer when we’re on vacation to snap our family photos! We have used Wendy from Flytographer 4 times in a row already!!

Jillian Harris Hawaii Recap

10. Where was Leo’s hat from that he was wearing in Hawaii?

It’s from a little company called Britty Brah!! They make the most adorable hats for both boys and girls!!

Jillian Harris Hawaii Recap

Photo Credit (images 3 | 4 | 5 | 6): Wendy from Flytographer

11. What sunscreen do you use for Leo?

I like to use Coola, Thinkbaby, and SunBum on Leo! I DO also use Thinkbaby on Annie too … I know you’re not supposed to use sunscreen on little ones like Annie but I did!

Jillian Harris Hawaii Recap

12. What are some of your favourite places to shop in Maui?

I don’t do much shopping anymore as I’m trying really hard to limit the number of items we have in our home. However, I do get gifted some really cute things from small shops which I love bringing with us but I don’t go out and buy much when I’m on vacation anymore. I used to love shopping while on vacay and I especially loved hitting up Sand People (awesome decor items!), The Fairmont gift shop (they carry so much amazing stuff!), Mahina (they have a few locations around Hawaii!) and my all time favourite place to shop is from THE LOCALS!!

Jillian Harris Hawaii Recap

Do you have any other questions for me?? If so, comment below and I’ll see if I can get to some of them!



Leave a Reply

  1. I know you like to travel to Maui often.. if you go back again, I HIGHLY recommend that you make a reservation (WAY in advance) for Mama’s Fish House in Paia. It’s the most AMAZING food I’ve ever had in my life. We managed to sneak in without a reservation (my husband and I) when we were there in December (at about 3pm for a late lunch/early dinner) and it was just as incredible as the last time we were there. The service is over and above too, the atmosphere is amazing and the food is to die for.

  2. Beautiful photos. That is not what my vacation photographs look like at all.
    Thanks for this q&a.. super helpful. Once our second child was born we waited a decent amount of time before we restarted our travelling.. we were so nervous to get back out there.. Looks like you had a wonderful time

  3. I’d love to bring my 2 year old on a trip but there are so many variables!! LOL What about carseats? And how hard is it to keep them on their napping schedule with the flights etc?

  4. I just watched the vlog so you answered my question about nap schedules! LOL
    Still curious about how you manage car seats though!

  5. I totally agree with the Sand People stores and Mahina. I was in Honolulu in 2016 with my daughters and Maui with my husband this past November and bought most of my goodies from Sand People!

  6. Thanks for the info. We are moving to Vancouver island in April and our first thought for a vacation is Hawaii!! U prefer Maui over the other islands!?? Thanks oh and what airline?? We love westjet. Sheri

  7. Hi Jillian! I’ve been dying to stay at the Fairmont Kea Lani ever since seeing your posts from there over the years! We are heading there in3 weeks for 10 days, can’t wait!! I’d like to take advantage of a spa treatment or 2! Have you tried their Willow Spa? If so is there a specific treatment you recommend? Can’t wait to try all your food recommendations! ?

  8. I was wondering if you had any tips for flying with a baby as young as Annie – when they don’t necessarily nap or toys don’t entertain them for long periods of time.

  9. How do you travel with your Dockatot? Previously I’ve disassembled it into a suitcase but is there an easier way that you do?

  10. Hawaii is on my bucket list to visit but I don’t know anything about the different islands and where I’d want to go. What can you tell a newbie about the differences between islands/cities, the atmosphere, things to do, etc.? Sounds like you would recommend Maui!

  11. Not sure you have ever dined at Lahaina Grill, but it was by far one of my favourite meals I have ever had, not to mention the service is amazing. Would highly recommend it maybe for a night out for you and Justin while you are there with his parents? 🙂

  12. Love following you on your trips:) we too are in love with Maui and esp the Mai Tia’s at Monkey Pod ? Enjoy your much deserved vacation with your beautiful family ?
    Hope you’re little darlings sleep well for you and you’re able to rest up:)

  13. I agree with you completely – traveling with a toddler and staying in a hotel isn’t ideal, so we always opt for Airbnb’s. We just got back from a trip and our Airbnb caught on FIRE in the middle of the night! It was terrifying. I’m not saying don’t stay in Airbnb’s (we still will) but please read my blog post about safety measures to consider.

  14. Other than your stroller what is a must have that you can’t travel without for Annie? Btw she is such a gorgeous baby! Those eyes of hers ?

  15. I love Maui too! The Fairmont Kea Lani was amazing – the villa is perfect with a family. I agree, we always need some kind of villa – but be warned when the kids are older and eating you out of house & home – villa with a kitchen is still very much needed!
    Have you guys ever tried Mama’s Fish House?

  16. I know you have traveled quite a bit with Annie already. In your opinion, how early is too early to vacation with a newborn? I am expecting with my first and we are trying to plan some trips but don’t know how long to wait after the babe is born! Thanks!

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