Maui Travel Diary

Maui Travel Diary

If you remember back, we started out the summer with Ryan taking swim lessons. One of the reasons we did so was to get him swim safe for our trip to Maui! We had been thinking about taking our first real, family of four, vacation and couldn't think of a better place to go. Maui is one of our favorite destinations and it holds a special place in our hearts. We honeymooned there and took baby announcement photos... no one really knew at the time that I was expecting Ryan.

Vacationing with kids is no easy task, but we survived and we will do it again! Seeing the boys experience the sites and sounds of Maui is something I'll never forget. 

What's in my suitcase?

There are definitely some things that you don't want to forget to pack when you are traveling with littles. Here are some of my must haves:

  • Portable baby changing mat - because you never know where you may have to change your toddler

  • Umbrella stroller - because you'll be able to stroll your little through the airport (even through security!) and allowed to check in the stroller as you're boarding the plane... my recommendations for single for one child and double for two children.

  • Sunscreen stick for kiddos - it's just so much easier to apply than the lotion kind

  • Toddler water shoes - these are the best when it comes to protecting their feet around the pool

  • Swim diapers - so your little one can enjoy the water without worries

  • Hair mask for island hair - because mamas deserve pampering while on vacation

And, here's my daily journal recapping our family's experience every step of the way... plus some of my personal recommendations for your own trip. I hope you enjoy!

Day 1: We’re on our way

As we started on our journey to Maui I wondered how the boys would be on the plane. I was expecting the worst with two active toddlers in tow, but it was actually kind of perfect.

As we were boarding, the flight crew invited Ryan into the cockpit to check it out. They explained to him how everything worked and even let him touch the buttons. They also gave him his own set of pilot wings… it was a super sweet moment for him. It’s a memory I’m sure he’ll cherish for a long time. Fun tip: next time you’re on a flight check with the crew to see if the pilot is willing to let your little take a tour of the cockpit. Your kiddo will have a fun experience (and possibly a moments) to associate with traveling.


Lollipops are a lifesaver in so many situations. We gave each of the boys a lollipop during takeoff and landing to help with the ear popping. Take off was right after lunch so the timing was perfect for Leo to take a nap. He fell asleep right after takeoff, as planned.

Ryan didn't end up taking a nap until the last 30 minutes of the flight, he was really good the entire flight, though. We got him some toddler headphones that he could plug into the speaker and watch some TV shows. I was nervous that he would get antsy and want to walk around the plane but he didn't.  


Leo got a little antsy after he woke from his nap. During our landing, he played with some ice chips which helped him take his mind off of his ears. We had to get creative. Art had two cups of ice and Leo would pick up one piece at a time and move it to and from one cup to the other. It was simple and did the trick distracting him. Tip: a friend suggested packing a small backpack full of toys from the dollar store to be able to pull out a new toy to distract the kiddos with every 30 minutes or so... I would have done it if I hadn't gotten the advice a day before taking off on our trip. It's worth a try, and I'll definitely be trying on our next big trip with the boys.


We arrived at the stunning Fairmont Kea Lani Resort

it was fun to be back with the boys! The staff were so welcoming. They lei’d us and gave the boys the cutest keepsakes, little necklaces with fish tales on the end. The boys actually wore them throughout the trip.

This article is sponsored by Fairmont Kea Lani Resort but all opinions are 100% my own. 


When we got to our room there was a beautiful presentation of champagne for us, a sweet welcome card, and some delicious dried fruit. There was also a beautiful crib set up for Leo which ended up being perfect for him, he slept there comfortably every night. It wasn’t before long that we got on our swimwear and headed to the beach to soak up the little sun that was left in the day with our friends… we planned this trip with them and their little daughter (she is about 2 months younger than Leo).


After the beach, we went to the Ama Bar & Grill located right by their pool. We did a casual dinner the first night, but it was yummy. I had the most delicious poke bowl entrée. They had a kids menu as well. A bonus is that kids under 5 eat free at 4 of the resort’s dining areas as long as an adult orders an entrée. Any time your travel be on the lookout for specials like this.

After we ate we headed to our room, we were all tired from traveling. When I hopped into the bathroom to take a shower I noticed the sweetest thing… the shower gel, shampoo, and conditioner was customized and said it was for It was such a personal touch that I really appreciated.

Day 2: Fun at the Pool & Beaches


We started off Day 2 by meeting our friends for a breakfast buffet at the Kea Lani Restaurant. We were excited to eat there again… we loved it while we were on our honeymoon. They do a beautiful spread and the fresh lilikoi juice is to die for! The food was as delicious as we remembered on our honeymoon, but it was a difficult breakfast with the boys. If you read my blog about mealtime with toddlers, you know we're in a stage where a nice sit down meal just isn't happening for us. 

After breakfast, we headed to the pool as a group. They have a bigger family pool, and then up in the terrace, a smaller pool with a slide that comes down into the bigger pool. Next to the big family pool, there's a splash pad just for the kids with a small body of water. That was perfect for Ryan and Leo, they didn't need their floaties and were safest there. 

The Fairmont was perfectly set up to accommodate families with young children. They had swim diapers on hand at their little pool shack and they also sell a variety of floaties, so if you didn't pack them you can pick some up. It worked out for us since didn’t want to have to worry about the room floaties would take up in the luggage.

We bought arm floaties for Ryan and we got a tube for Leo, but he hated being in that so we carried him most of the time in the water. Although Ryan is swim-safe, I still wanted the arm floaties on him so he could hang for a bit on his own without me right next to him.

We ordered lunch at the pool which was really easy, we loved being able to do that. The boys were well behaved eating poolside. I think it was more fun for them than being at a lunch table and confined when all they wanted to do was explore. Art took Leo for a stroll and he took his usual nap. We made some shade for his stroller by the pool and he slept.

I took Ryan to Polo Beach for the first time, it's right off the Fairmont Resort, you can just walk onto the beach. Ryan loved the waves, he was in his element smiling ear-to-ear. They have shaved ice station set up as you're coming off the beach and I got Ryan some… he loved it. He was definitely living his best life. It was so nice to have some one on one time with him.

We headed back and met our friends again at the pool for a little bit before we decided to head out to Big Beach in Makena together. Big Beach is known for its golden sands. Ryan and Leo were having so much fun building sandcastles with their  friend Teah… it was really sweet to see them together. The tides are a little bit stronger there so Art and his friend Alex did some boogie boarding.


Big Beach holds a special place in our hearts too… we did our baby announcement for Ryan there, nobody really knew I was pregnant at the time. It was special to be back again this time with Ryan and Leo.


We stayed for a few hours then we headed back to the hotel pool again. We ordered some quick bites just to get the kids fed and ourselves fed by the pool. The menu had all the things that kids love... mac and cheese,  fruit cups, quesadilla, chicken tenders, and more. We spent some more time in the pool after then visited the jacuzzi before heading up to get ready for bed.

Maui’s 3 hours behind LA so we were always thinking about the number of hours we were putting in for the day. The time difference was a benefit too… the kids were super exhausted and really easy to put to bed, parenting win! They slept in a little later than normal too because we were trying to do so much all in one day, but it worked out perfect for us.


Day 3: Hangin’ at the Resort

We headed down to breakfast at the Caffe Ciao Bakery + Market with our active boys while our friends ate at the buffet again with their sweet and well behaved girl haha. It was so much easier to get the boys fed in this order and go style.


Once we were done with breakfast we met our friends over at the pool splash pad. The kids loved playing there so much that we stayed through lunch time. The Fairmont splash pad is a definite plus for any families with young children! Daddy bought Ryan a pair of pool goggles at the resort called Poolgles. Ryan thought they were the coolest, even in the splash pad. 

This was our resort day so Leo took a nap in the room this time. Daddy got to go up and catch up with some work while Leo slept. Ryan and I spent more time at the pool and I discovered my favorite (adult) drink at the resort this day, it's called the pomegranate cucumber mojito. I highly recommend! It was so good that it ended up being my drink of choice for the rest of the trip.

We all got freshened up, got into our nicer outfits, and we headed to eat at Tommy Bahamas in the Wailea Shops. My girlfriend who was with me is actually a designer for Tommy Bahama Swim, so we were all  super excited to see all of her designs in the Wailea store.


It was a beautiful place to dine. There was live music and the food was delicious. It was a good family restaurant too! I'd recommend Tommy Bahamas if you want to have kind of a semi-fancy dinner, but nothing too fancy, that you can still go and enjoy with your family.

We wrapped the night up, but Ryan and I weren't ready for bed. We wanted to explore and walk the resort grounds. Art took Leo up to bed and Ryan and I walked the resort grounds, I just wanted to see it all at night. It was really beautiful!

We ended up seeing a sweet mama cat and three little baby kittens that were just walking around on the resort… I think they were probably looking for some scraps of food. Ryan thought that was really cute and was so excited to see them.

Ok, now we were ready to call it a night. 

Day 4: Napili Beach


Day 4 started off just like Day 3, by eating breakfast at the Caffe Ciao Bakery + Market. It was so easy we decided to eat there again. It was perfect, the boys ate well. After breakfast, I headed to the pool with the boys and Art had a little beach time on his own… he got a little snorkeling in.

We decided that we were going to visit our favorite beach on Maui, Napili Beach. It's just so gorgeous! The waters are super calm and the sand is perfect. We planned it so we would leave around noon, that way the boys could take their nap on our drive up. It’s about an hour drive from Wailea to Napili Beach, and it's definitely worth the drive to see the other side of the island.


It was great to have a rental car to beach hop. The resort shuttle will take you to certain places, but we didn't want to wait for shuttle hours, and we wanted to explore beyond just going to the airport or going to dinner and to town. We like seeing different parts of the island and the freedom of going when and where we want.

We ended up eating at Ono Tacos on our way to Napili Beach, it's a taco truck that is pretty famous on Maui. We’ve eaten there on previous trips to the island and the food never disappoints.


We stayed on the beach until sunset, it was the most magical sunset ever! Ryan loved being on the beach, I feel like he would sleep there if we let him. You can already see he's an island boy like his daddy. 

We got back to the room late and decided to take advantage of in-room dining. We got the boys in the bath and ordered pizza for them so once they were done they could enjoy before going to bed.

This day was perfect all around!


Napili Recommendations:

  • We didn't have a chance to go to the Gazebo Restaurant on this trip because they’re a breakfast/brunch place and they close at 2pm. It's one of our favorite spots to eat. They have amazing pancakes and fried rice dish there. So, if you're on the north side of the island, near the Napili beach Kapalua area you’ll definitely want to try out the Gazebo.

  • If you have time you’ll also want to check out Kapalua Beach which is amazing for snorkeling and seeing turtles. Sometimes the turtles just come up right there on the rocks. It's really beautiful to see. It’s a little windier, but it's lusher as well.

Day 5: From Day Trip to Impending Hurricane

We split off from our friends and decided to do breakfast at Kihei Caffé. It's a little local spot in the small town of Kihei neighboring Wailea and I highly recommend it. They have the most amazing pancakes and rice dish there. The rice dish is called the Loco Moco and it comes with two eggs, fresh ground beef patty, rice and brown gravy.

There were chickens and roosters walking near the Kihei Caffé area… the boys loved seeing them. If you go there be mindful that the chickens and roosters will peck at your legs. It sounds kind of aggressive, but it's really not, they're just trying to eat everybody's scraps of breakfast.


After that, we decided to drive down past our hotel again to get to the Lava Fields at La Perouse Bay. It’s really cool to see the lava fields where it's past volcanic rock. We hung out there a bit and then headed back to our hotel to meet our friends for some pool time.


Why we stayed at the resort for dinner:

The real reason we decided to stay on the resort for dinner was because of the impending storm, Hurricane Lane.

We knew that the hurricane was on its way, but I'm not one who likes to watch the news, because I feel like the more I watch it the more worried I get. There was a lot of talk when we got to the resort, then not so much, then a lot of talk again.

People were super fearful about what was to come. On this day of our vacation, Hurricane Lane was declared a category five hurricane and they were saying that it was going to be the strongest hurricane to hit the Hawaiian islands since a hurricane in 1994.

It brought a little panic to the whole vacation and we saw people on the resort getting a little more worried and hesitant. This added a little stress to the last leg of our vacation.

The mood at the hotel was a little bit more anxious, but they were really good about keeping everyone calm and assuring us that they were prepared should anything happen… that they had ample water and food for everyone at the resort. That made us feel more secure, but it definitely scary to have that thought in the back of our minds that a hurricane could hit any time.

They were saying that it was gonna hit the day that we were gonna leave, which we expected. We tried to enjoy the last leg of our trip, but at this point, we were already all a bit anxious, especially being with little ones on vacation and hearing something like this.


We headed up a little bit earlier to get ready for a more formal dinner at Nick's Fish Market which was located in our resort. It started raining while we were there, but it was beautiful to hear the rain and the ocean. The restaurant was indoors, but it was open all around.


The food was delicious. We ate here on our honeymoon, too. Even though it was a fancy restaurant, they were super accommodating with kids. They brought them Goldfish snacks, crayons, and some coloring paper.

Leo ended up falling asleep in the middle of dinner. We were able to enjoy dinner with just Ryan, our friends, and their daughter. It was a really nice last dinner on Maui. After dinner, we headed up to the room for the night.

Day 6: A Hui Hou Kākou Maui

(Until we meet again Maui)

We woke up to a gloomier morning on our last day at the resort. It really felt like the hurricane could come at any time… every other morning it was so sunny. We were super sad to go, but we were thankful that we would hopefully be leaving before Hurricane Lane hit.

We grabbed breakfast at the Caffé Deli again, this time with our friends. We were going to try the buffet one last time but decided not to because the line was sooo long. The hurricane threat caused everyone to stay at the resort to eat so it was busier than normal.

We stopped over at the resort shop, Le Surf Wailea, after breakfast… it was a really cute shop. They had a variety of things from clothing to swimwear to toys. We figured if we were going to keep the kids indoors then we should get something to entertain them with. We picked up some play-doh and headed back to the room. It helped distract they from the anxiousness that everyone was feeling.

We headed over to our balcony and noticed that people were still at the pool and on the beach. No one was really swimming in the ocean... there were red flags out to signify it was dangerous to swim.

After Art got some work done he took Ryan to the beach to play in the sand. We wanted him to have some fun and not be cooped up in the room all day because we were afraid of the hurricane. Leo was unusually tired so I stayed in the room with him. We both took really long naps. It was nice because I didn’t sleep well, I was anxious about the hurricane. When Leo woke up we went back to the Deli Caffé and grabbed some food.

We made our way back to the room and I started packing our things. We had to be at the airport around 5-5:30 p.m. for our red-eye flight. I give myself a couple of hours with breaks in between because I hate packing… haha.

On the way back home we took Hawaiian Airlines. It was really nice because we were able to upgrade to first class seats... it was so roomy. We had a separate seat for Ryan, but Leo was a lap baby.

Leo was a little more sensitive when it came to his ears on the flights, he was crying his eyes out. We didn't have that issue as much with Ryan. We did get the recommendation from our pediatrician and a few other people to give Benadryl before a flight… that's something parents might want to look into. We personally decided that we weren’t comfortable doing that. They say with Benadryl that there's a chance that your child may become hyper as opposed to relaxing and napping.

This red-eye flight ended up not working out the way it did so well with Ryan on a previous Hawaii trip. He didn't sleep very much until the end so I felt bad. We had the lollipops ready for both takeoff and landing, so it helped a little bit but still, it was a little bit hard.

We were happy to get out of there on time. We were told that the hurricane was downgraded from category five to category four and then finally category three right before we left. Thanks goodness!

And, it was a wrap on our first family (of 4) vacation!

Ps. Thank you to everyone who left their sweet messages on Instagram and kept us in their thoughts and prayers. We ended up totally dodging Hurricane Lane.

A Few Tips to Note

Tip 1: Add on two extra days.

Foreal… however many days you think you need on your vacation add two more. The first and last days are pretty much a wash because travel days are so much more involved with little ones… the packing, unpacking, getting organized and getting settled. When I was just Art and me, those days weren't a wash because we could do so much and we could just pack light.

Tip 2: Rent a Jeep if you want to explore.

I say this because it's so fun to have a Jeep on Maui. It just feels like what you are supposed to do when you're going beach hopping. But obviously, you can rent any car you want, the Jeep ended up being fun and perfect even with the two car seats in the back.

Tip 3: Do some car seat research.

Car seats are flimsier at the rental places, they're not gonna be the ones that we have in the States. The only way the car seats fit tight in the car was when they were facing forward otherwise they were moving around like crazy. I guess in Hawaii forward facing seats are used when children are at least 1 year old, have outgrown their rear-facing seat, and are at least 20 pounds. On our next trip, I may consider lugging our car seats over or looking into other options for renting car seats.

Tip 4: Spend one on one time with each child.

We tried to have a little Mommy and Me and Daddy and Me time with each of the boys. It was really nice to take time out with each child to make them feel special.

Tip 5: Check into Nanny services

Parents going to Hawaii who are looking into more date nights and alone time may want to look into nanny services. I met a nanny at the resort that was hired by a family and she was so sweet. She said she came through Nanny Connection. On this vacation, we had personally chosen to be with our kids and enjoy the time with them so we didn’t go the nanny route, but this is a great option to have.

Tip 6: Take the red-eye on the way home.

This may sound nuts, but it actually works well… for the most part. I like the idea of the red-eye because one parent can just hold the baby and they will sleep through the flight. We did it with Ryan on our Oahu trip and he ended up sleeping the whole flight... it was super easy. This time it was a little harder to manage with two kids.

Tip 7: Check out these places if you can.

  • Kaanapali - A very touristy area with a shopping district and various activities to explore.  It is also known for Black Rock, a popular place to snorkel and rock jump

  • Old Lahaina Luau - Authentic Hawaiin Lu’aus, traditional cuisine, music, and cultural dances

  • Hali'imaile General Store -  An unknown restaurant off the grid on the countryside of Maui. They have delicious food and it’s an amazing date spot.

  • Star Noodle - An excellent ramen spot with amazing donuts called, Malasadas.

  • Road to Hana - An excursion highlighting the beauty of Hana while learning the history and legends of the area. You can drive yourself or take a tour.

  • Haleakala - Go above the clouds to see the sunrise

  • Mamas Fish House - A super popular restaurant you’ll want to make reservations for.

This was such a beautiful trip. It was nice to be away with family, but of course it ended up being a lot of work… prepare yourself. It's not easy running after toddlers in the sun and reapplying sunscreen a million times and making sure the kids are fed as they're swimming around and exploring a new place. The work doesn't end on vacation, but family vacations are fun and it's all about the memories so take lots of pictures!

Shout out to the Fairmont Kea Lani Resort for making this such a great trip. Everything from our room, staff, beaches, pools, restaurants, and in between was amazing! We can't wait to go back!

Mamas, share what some of your fondest family vacation memories are! 

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Elle Rowley of Solly Baby

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