A Hawaiian Christmas


A Hawaiian Christmas

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What a joker my son is. He’s on this kick now to give this ridiculously over-the-top mad face when he’s told to smile for photos. It’s like tough guy meets playground bully, except in a cute 5-year old body.

This year we were lucky enough to get to spend Christmas week in Hawaii on the beautiful island of Maui. It was a trip to celebrate my Mother-in-Law’s 70th birthday and retirement!

It was an amazing trip and I thought I’d share some highlights from it!

Hawaii Christmas Spirit

I had never been to Hawaii before and the island immediately hit me with a feeling of respect. There is much history there, both good and bad, and more than I could possibly learn about in a single week (especially with two kids). I did my best to honor the place by trying local foods and activities and be mindful of where we were walking, what we were using, and how we were treating those lucky people that call Hawaii home.

Basically my motto for the trip was RESPECT.

Oh… and roadside coconuts, which I kind of became addicted to.


Once our kids realized we had escaped the winter for a fleeting week, they immediately embraced what I called their “Hawaii look”.

This one has serious style. I can’t handle it. I’m sure we will NEVER fight when she is a teenager.

The dude has been rocking this more athletic look – long socks and shorts. He truly believes this makes him faster and so far I haven’t been able to disprove it.

Mom thinks it looks weird. Dad thinks it looks pretty dope.

All The Hawaii Things!

With many vacations, but especially this one, there was an intense feeling of missing out. When you walk off the plane you are smacked in the face with a million different “once-in-a-lifetime” trips, excursions, and experiences.

These can be fun, but we took a different approach this trip – partially just to save money. We planned short adventures in the morning to mostly free landmarks in the interior parts of Maui or along the coast. We visited Iao State Park to see the Needle, which was really cool, and also saw the famous blowhole on the Northern shore of the island.

Some days though we just walked around our resort area and let the kids explore. They were very good at finding and petting feral cats, which I was against initially, but I was reassured that the cats are well cared for near the resort where we were staying. We still washed hands pretty vigorously after the feral cats…

The only scheduled activity we did do was a classic Hawaiian Luau! There are SO many of these… it’s hard to know which is good. Our group chose a really great one called the Feast at Lele. The food and entertainment was from five different pacific islands so you got a taste of a ton of different cultures.

Dad loved the mai tais and the kids loved the special strawberry drinks!

As the night wore on and the dancing really started, our three-year old couldn’t help but dance. She loves dancing and has zero fear of standing in front of 200 people and dancing. She will probably grow out of this phase, but I hope she never does.

No Kids Date Day!

Even though we love our children, Betsy and I really find that we are much better parents if we get some time without them. I cannot recommend this enough on a family vacation. Get a babysitter from a trusted source and spend a day doing adult things!

We had six hours of non-kid activities one day which we spent snorkeling with sea turtles in Honolua Bay (not guided – just on our own). We also got some beers from Maui brewing company and had some super fresh Acai bowls and just sat in peace and quiet next to the beach.

Worth. Every. Penny.

Traveling Update

I would classify our kids as decent travelers. They are pretty flexible with most things and do okay on planes and stuff. One thing we have always struggled with is car seats. Checking them is such a pain in the butt and renting them is expensive.

For this trip, we tried something new. We borrowed these cool harnesses from our neighbors – who travel more than we do. There are a few different brands of these, but I had never seen them before. The kind we tried is the WhizRider. The harness rolls up and fits easily in your carry on. The kids strap it on and then it hooks into the normal car seat belts!

If you’ve ever rock climbed, the harness has a similar feel to it. Luckily, we didn’t have to test out the full safety functionality of it, but it felt pretty safe to me and has really good safety ratings. We will absolutely be investing in these for our next big trip!

Of course, even with good kids, traveling can be hard. Our three-year old really struggles with transitions right now which makes airports brutal. She had a full starfish tantrum that lasted about 15 minutes in the middle of the Maui airport on the way home.

The reason: We had to put her “Lambie” doll through the Xray machine.

Parenting is fun.

I doubt we will be able to return to Hawaii any time soon. As with any trip, there are things I wish we were able to do, but also thankful for the things we got to experience.

Whether your holidays find you in a warm location, cold location, or just at home snuggled in, the Macheesmo family wishes you a very happy holidays and happy 2020!

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