My family and I recently spent seven days in Maui! It was our first time visiting Hawaii and our first flight away from the mainland since November 2019.

Coming from the Northeast to Hawai’i is quite a trek, especially with a preschooler.

But we’re hoping that soon we’ll be able to return to visiting family in The Philippines soon, so this was a good prep trip for us. It’s almost exactly half the distance in miles and half of the time difference–there’s a six hour difference between Hawai’i and Connecticut, and a TWELVE hour difference between here and Phils. The difference is night and day. …pun intended.

It helped that we’ve been checking out Vox and Wonderbooks from our local Library. These books have a speaker attachment that allows a preschooler to press “play” and have a prerecorded voice actor read the book aloud to them. The plane was the first time he’d used the earphone plug in feature, so that was the only “new” aspect. And, of course, he overindulged in in-flight TV, putting his tray up and down, and accidentally kicking the person in the seat ahead of him while I would correct him loud enough for his victim to overhear.

The flights and layover were long, especially the hour + it took for our preschooler to get to sleep for a nap while the guy across the aisle was the only one in the vicinity with his window open. But we landed safely in Hawai’i and all was worth it!

We arrived at our hotel in Wailea around 4 p.m., but it was bedtime on the east coast & we had a sunrise family photoshoot planned with Love & Water photo, so we ordered in while I got our clothes ironed & settled in. We stayed at a regular hotel, not a resort, because I like to spend travel seeing as much of the sights I can and indulging in all kinds of adventures. Our hotel cost was covered by points accrued from previous travel + our Marriot Bonvoy Amex Card.

The next day, I was up around 3 a.m. Hawai’i time, the rest of the fam later for the shoot. I’m looking forward to the full set of photos from Love + Water in a couple of weeks, but here’s the web preview they sent!

Following the shoot, we had breakfast and shopped around at a Saturday Farmer’s Market in Kihei where the Maui Ono Donuts truck was posted up while we waited for our ten a.m. surfing lessons with Surf Shack Maui.

I did a lot of research on which Surf Lessons would be the best for our family. At first, I was intending on all four of us taking private lessons together as a family. After some searching, I discovered a vendor that taught kids of any age. Right as I was about to book, I remembered that my three-and-a-half-year-old son doesn’t even know how to swim! He’s in lessons but I scrapped that, my husband and I agreed on just me and my older son giving it a go, and I came across Surf Shack Maui. They have two locations and teach group or private lessons for people ages 5 and up with complimentary rash guards, surf booties, and a photographer to chronicle it (though files of the photos come at a small fee). I thought this would be a good pick for us because it was close to our Wailea hotel and they’re also a surf rental shack, so we’d be able to rent boards and other stuff from them if the lessons went well.

The lessons did go well.

Before lessons began, Tobias was telling me how he was going to be a far better surfer than me. He is a better snowboarder by all means, and he’s taken up skateboarding over the last few months. But I’m overall a faster learner and work out a lot more.

After the initial on-land lesson, I thought the competition would be close. The steps to go from laying on the board to standing was a lot like “downward dog–cow pose–lunge–stand” and I thought my yoga training would give me an edge.

I caught the first wave for longer, but we both thought ourselves pretty good rather quickly.

I always wanted to surf. I grew up in a little beach town in Texas called Corpus Christi but dreamed of being a California surf girl. That’s not something that drives me now, but I wanted to get back out there soon.

A couple of days later, we did make time in our schedule to come back for more at Kihei.

We rented only one board, because my youngest wanted me to play with him on the playground and the beach. The playground was great, and shaded!

There were also many feathered friends frolicking around.

But after some time out there, my oldest came back defeated. He hadn’t caught a wave, was beat up by the rocks, and wasn’t having fun. I couldn’t believe it! He was such a natural when we got our lessons.

I offered to go out there with him and figure out where he was going wrong. He wanted a break. I decided I would get out there and try and catch some more waves. I’d try and see where he was going wrong.

I kept missing the waves, too.

I noticed that I would see a good wave, go for it, and by the time I was standing (if I even got that far) I’d be standing on flat water, watching as the wave carried on without me. Then another good wave would come, and this one guy would be riding it. He kept catching these good waves shortly after the ones I attempted, so I started subtly watching him and trying for the same waves. Eventually I struck up a conversation.

He was Canadian and had been on several surf trips, but also still considered himself very much a beginner. I explained that it was my second day out there, my first without a lesson, and how I was trying to figure out what my teen son was doing wrong before returning to report back, but I hadn’t managed to get it right myself.

As the water splashed gently at our backs, he said: “It’s much easier when you’ve got someone to give you a push.”

That was it! Our instructor had been alerting us to paddle quickly and cueing us in on the motions to take to get to standing. He was watching for the good waves and he gave a quick push to the board that our paddling only supplemented. I needed a push.

Thankfully, my new Canadian friend offered a push, and picked out the right wave for me.

I rode that wave all the way to the coast!

I decided I’d head right over and let my son know the secret–we’d just take turns giving each other a push as we improved our competency.

Unfortunately, he was dry, worn out, and unconcerned about surfing for the day.

I left our first surfing experience with a few reminders:

1. Much like bowling, leave the bumpers up when you’re learning something new. You don’t get a medal for doing things the hard way, but enjoying yourself in the process is reward enough.
2. Learning always happens faster with a friend. If you don’t have one, make one.
3. The only way you can get better is to admit you’re not doing well. Preferably loud enough for someone helpful to hear and to give you a boost.