Maui Family Vacation : The Good, The Bad & The Ugly

Purchasing through links we share keep our glasses full of wine, read our full disclosures here.

Aloha! We are officially back in the swing of things after our Maui family vacation! This being our first family trip with TWO kids, I can’t wait to give you the run down! You may have seen this list of tips for traveling with little ones that I compiled from my experiences traveling with one, so I’ll share how we used a few of those items. Traveling with two definitely added a new list of challenges, but I also had my hubby to help this time around. So here it is, the recap of our Maui trip!

Family Vacation Maui

Here’s a bit of background:

I have been going to Hawaii every few years since i was about 8 years old. It is one of my favorite places on Earth, and I dream of making the islands my home one day. I have visited the Big Island, Kauai, Oahu and Maui. Many of our trips include extended family like aunts, uncles and cousins, and we’ve found our “go-to” spot in Maui. Our last trip was back in 2014, when Maverick was just under a year old. He wasn’t walking just yet, but took a couple teaser steps during my cousin’s beachfront wedding.

This last trip was shortly before my husband and I began dating, so it was just Maverick and I. The trip we just returned from was actually has first visit to Hawaii ever, so I was extra excited to share this place that held such a  special place in my heart with him.

Carter actually had his half birthday while we are there (18 months old), so he is just slightly older than Maverick was during our last trip. Carter has notoriously been a bit more challenging than Maverick was as a baby. Combine that with teething, I was more than just a little nervous about how our flights would go.

The Good

Our Resort

We stayed at the breathtaking Westin Ka’anapali. Upon arrival, this place looks like something straight out of a travel brochure. It is GORGEOUS! We ended up with an awesome set up in a one bedroom suite, with my mom in a connecting studio lock off. Hello babysitter! Joking, kind of. A few other family members were also staying at the resort so it was nice to have everyone centrally located.

Maui Family Vacation, Westin Kaanapali
 Not a bad view for my morning coffee…

The best part about this place for us was how incredibly family friendly it was. Not only is there a kids club and child care available (which we didn’t use), there is a ton for kids to do at the resort. There are multiple pools on site, one even has a pirate ship playground in the pool which was an obvious favorite for our little guys. The other pools boasted their own sweet perks like a water slide or volleyball net.

I somehow went the entire trip without a single picture of the pirate pool! Talk about a mom blogger fail! Thankfully, Hawaii Mom Blog has a great review of the whole resort and some awesome pictures too. Check out her review for more great details on this gorgeous resort! Seriously, this place is not to be missed!

The Westin Ka’anapali Pirate Ship, courtesy of Hawaii Mom Blog

The Gear

The resort is beachfront, so we were able to walk right down to the water. We picked up some beach chairs and umbrella at the Snorkel Store so we could have a comfy set up with the kids. Their Mobile Beach Cabana costs as much for a week as it would to get chairs from the resort for one day, so it was totally worth it to make this slight detour ahead of time. They also have amazing customer service!

Tip: If you didn’t come with a UV shirt, GET A UV SHIRT. The Snorkel Store offered us a good deal on long sleeve UV shirts and we declined. My husband and oldest son both got a wicked sunburn by day two and we regretted the decision. We ended up paying more somewhere else, after half the family was already burnt. I also snagged this super cute Women’s Long Sleeve Swimsuit Top on Amazon for future sun outings. Maui Realization: I’m officially to that age where I care about UV protection more than I care about coming home with a tan.

I also brought along my SandCloud XL beach towel for a large beach blanket, knowing the resort towels wouldn’t be big enough for us to spread out. It was perfect, and was big enough to wrap around me and the boys. You can snag yours on their site, but be sure to order through this link to get 15% off.

Other than our trips into Lahaina for shaved ice, a luau, and a date night, we didn’t leave the resort. And that’s how we like it! There was more than enough on site to keep our family busy, happy and relaxed!

The Luau

Maui Family Vacation, Old Lahaina Luau
A rare shot of all four of us! That was enough to make my night!

The Old Lahaina Luau is another favorite for our family. This is where my cousin had her reception a few years back and they truly put on an amazing show. We knew we had to make another visit. The food was delicious, and they were very helpful when it came to food allergies in the family.

I got a special picture with Carter to recreate one I got with Mav four years ago, but I almost did’t have the guts to post it. You can read more about that here.

Maui Family Vacation, Old Lahaina Luau

We even got a family picture which almost NEVER happens since my hubby is not a fan of pictures, which is pretty funny given my obsessive picture taking and blogging. Sorry babe!

Maverick’s favorite part? “The shaking”… Oh boy, am I in trouble?!?!

Maui Family Vacation, Old Lahaina Luau

Aside from the usual pig ceremony and hula show, they also have various activities to great you when you arrive. Mav took a hula lesson, learned about Hawaiian music and instruments, and we looked at some locally made jewelry and art. It really is a great night for all!

The Flight Home

This originally looked like it was going to go on the “Bad” list, but a hero of a super mom totally saved the flight. I want to be her when I grow up. Here’s why:

Early on, Carter made it very clear he was not feeling the vibe. I went through my entire bag of snacks, toys and activities trying to avoid a meltdown in about 30 minutes. He was losing it. This was going to get ugly.

Maui Family Vacation, The Flight


Out of nowhere, she pulls out the EPIC mom bag and hands him a toy that kept his attention for a full 30 minutes. About 29 minutes longer than anything I had tried! She did the same with a fussy child a couple rows up and instant happiness.

When the drink cart came around, I anxiously ordered a half bottle of wine knowing I was going to need all the help I could get to survive this long flight. She ordered the same! I so badly wanted to introduce myself to the amazing wine-loving mom hero, but I am so awkward in person all I could muster was a smile and an across the aisle air cheers. Damn my shyness! I totally feel we could have been mom friends!

Maui Family Vacation, The Flight
My wine, and Super Mom’s husband’s leg in the background. If this is your man, speak up so we can become MFs (mom friends, duh)!

She stayed cool, calm and collected throughout the flight with her three kids, and even saved Carter from the brink of meltdown two more times before we landed. I’m telling you, this woman is a saint & a goddess. If you were the one that flew from OGG to SJC on 7/14/18 and you enjoyed half bottle of wine while saving my ass – say hi! I’m far less awkward online (I think!). This could be the start to an awesome friendship (and a lot more wine ahead!)…

Date Night

We got lucky enough to sneak away for a fancy date night with just me and the hubby (thanks mom!). If you know us, you know how truly rare this can be. We are about to celebrate our one year wedding anniversary and I can count our date nights as husband and wife on one hand. Fancy date night? It’s been a few years.

Special shout out to all of you voted on which dress I should get! I got so many compliments! If you want to see all four dresses that were in the running, you can check them out here.

Family Vacation Maui: The Good The Bad & The Ugly

We chose Kimo’s in Lahaina for dinner. It is right on the water so we got to watch the sunset from the patio while we enjoyed an AMAZING meal. They have a handful of fish preparations they specialize in, and the daily catch dictates which ones they serve that evening. I went with crab stuffed, Anthony went with Kimo Style with a sweet basil aioli.

I honestly don’t think there is a wrong answer on this menu. Next time you are in the area, make it a point to head over! It is family friendly, but also made for a great romantic date night.

Family Vacation Maui: The Good The Bad & The Ugly
Fire-side mai-tai with the waves just behind you. Yes please!

When we got back to the resort our boys (and my mom), were asleep, so we ended the night with a late night happy hour at the hotel’s bonfire by the beach. Could not have been a more perfect evening.

The Bad

Travel Day(s)

I felt like we were SO over-prepared for traveling with two little ones, but I was reminded there is no such thing. It started with a wild ride through San Jose Airport at 5 am.

We got the Car Seat Travel Belt I recommended, but trying to attach it to the suitcase before the sun comes up and the coffee kicks in was just way beyond me. Which is quite ridiculous since I had tested it out before hand, and well, it’s ridiculously simple. About half way through the flight it clicked what I was doing wrong and it was smooth sailing with that the rest of the trip. Tip: it attaches AROUND the suitcase (just like in the picture), not around the handle. Fail. Once again – it was VERY early!

San Jose Airport TSA

This gets it’s own category because it was a straight up mess. I’ve traveled through this airport before and while it can be fairly busy, it’s one of the easier to navigate. Adding two small children and car seats and all that can make it a bit more challenging, but nothing we couldn’t handle.

Then we hit TSA. Getting through the initial ID check was fine, and they directed us altogether to a line to go through all the machines. This is where it got dicey.

First thing they did was ask Anthony to pull our car seat and stroller through a separate machine, separating him from me and the kids. They then took them and made him go through a separate machine. In them meantime, I’m feeding the rest of our belongings through the x-ray machine and preparing to walk through with the kids. At the last moment, they pull my four year old away and make him go through a separate line. Alone. In a busy airport.

So at this point, our family and belongings are being run through FIVE different lines. It all happened so quickly, I barely had time to process it all. When I tried to object to being separated from my son, I got a stern “Ma’am, please cooperate”. We completely lost sight of our bags, wallets, phones, etc. Not to mention my four year old was ALONE. I was livid and more than a little shaken up trying to run from line to line to collect our family members and belongings.

Luckily, The airport in Hawaii seemed to route many of the families to the same line and the process went much smoother. We all went through the same line, and were never separated. Can they share some of that Aloha vibe with the TSA agents in San Jose?

If you have the chance to, I HIGHLY recommend getting TSA Pre-check prior to traveling. We obviously did not, and paid the price. Anyone in your party over age 13 would need their own Pre-Check designation. Travelers in your party 12 and under can all go through Pre-Check with a parent who has it. Pre-Check streamlines the security process and I can see the fee being TOTALLY worth the lower stress level. There are a number of travel cards that also reimburse you for the Pre-Check fees!

The Ugly

There was none. We went to Hawaii for goodness sakes! With our crazy schedules, I would have been pretty darn happy with a stay-cation and getting some extra time together. But hello? A week in paradise? Things can got a little sideways at moments, but we were still in paradise!

Maui Family Vacation, Butt Wiping

The Very Best Part

On day two Maverick decided he was ready to start wiping his own butt! Just in time for kindergarten to start next week! Hooray!!

Our Next Trip

This trip definitely reminded us how important it is to slow down and enjoy the moment. Our children are growing and changing so quickly, it was so amazing to see all this through their little eyes.

Family Vacation Maui: The Good The Bad & The Ugly

I also convinced my hubby we should plan a trip for just us, since our kids also flexed some independence while we were there. In the three years we’ve been together, we haven’t had more than an overnight away from the kiddos. I think we are due!

I’d Love To Hear From You!

Have you been to Maui? What are your favorite spots? Where should we head for our Grown-Ups only trip? Share it all in the comments!


Amy Manos Signature







Family Vacation Maui: The Good The Bad & The Ugly Family Vacation Maui: The Good The Bad & The Ugly Family Vacation Maui: The Good The Bad & The Ugly

Ready For Your Next Vacation?

Pinot & Parenting has paired up with Middle of The Magic Travel to help make your next trip extra special without all the stress! Senior Travel Planner Heather Wilkinson specializes in all things family travel, including family vacations all around the world and OF COURSE those always magical Disney trips!

She can’t wait to help you plan your next getaway. It doesn’t cost anything extra to book through a travel agent, and she also has access to exclusive deals and experiences you wouldn’t be able to book on your own. The best part is, Heather can plan every aspect of your trip to take the stress off of you. You just have to get the airport!

Leave a Reply