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What We Did Right – and Wrong – on a Recent Trip to Maui

In the 15 months since the Joy Boys were born, we have traveled from LA to New York, LA to San Francisco, then moved from LA to Hawaii, traveled from Hawaii to LA, San Francisco and Mexico, and then made the 10-hour flight from Honolulu to New York and back.

I thought going to another island for 6 days, a 35-minute flight, would be a breeze. Not only was it a short trip, but we were meeting up with my best friend, her husband, and her daughters (age 10 and 13) who are old enough to babysit.

But I was wrong, on some levels. Turns out taking your twin babies anywhere, even just a short distance away, is nearly as much work as taking them on a trip across the entire Pacific Ocean and continental United States. Just a shorter plane flight.

Mama & Joy Boys at resort

We still had to pack our clothes and toiletries, their clothes and meds and toiletries, their double stroller, their 2 car seats, and a carry-on bag loaded with toys, diapers and snacks, as outlined in my post How to Handle Travel with Your Infant Twins Like a Boss. We still had to rent a car. We still had to shop for diapers and wipes and snacks upon our arrival. We still had to arrange for 2 Pack n Play cribs to be waiting for us at our rental home.

Most importantly, the boys still had to adjust to a whole new place. T does better with this than Z.

Here’s what I feel we did right and wrong. Hopefully you’ll find it helpful.


  • Showed up to a lovely AirBnB with a full kitchen and washing machine: so crucial when traveling with kids! You’ll be so happy to be able to eat some meals and do some laundry if staying anywhere for more than 2 days.
  • Got the landlady to provide 2 pack n plays and 2 high chairs (kind of a miracle!)
  • Have sleep trained the boys so that they nap during the day in their pack n’ plays covered up with a dark blue sheet. We bring these sheets with us when we travel, cover them up when it’s time to sleep, so they don’t get distracted by their surroundings. It works like a charm! I got them to go down for nap and bedtime with no fuss the very first night we were there… And one pack ‘n play was stuffed half-way in a closet because there wasn’t room!
  • Didn’t plan too much. One major activity each day. On the first day, we super enjoyed a two-hour lunch with my best friend and her family at Mama’s Fish House. This was genius because I had us go at 11am, right after the boys’ morning nap and well in advance of their afternoon nap. The restaurant is on a small, almost private beach, so while we waited for our food to arrive, the boys were able to run around, play in the sand, jump on an outrigger canoe, and otherwise wear themselves out. Meanwhile, Mama and Jen got to enjoy a mai tai (see below). Mostly, we had lunch out, but picked up dinner out and ate it at home. One day, we bought veggies at the farmer’s market and grilled them on our BBQ.

Mama & Jen enjoy a Mai Tai

  • Spent a lot of time outside in nature. This always makes my boys happy and calm. One day, we went to the beach. Another day, we spent at my best friend’s fancy hotel pool. When the boys got a diaper rash, we just stripped them naked and let them run around the beach. They were thrilled.

Naked Babes Hiking


  • Moved unnecessarily. Why, oh why, did I not have us stay at the same house the entire 5 nights? I was completely out of my Mama mind when I booked us at one place for the first 3 nights, and another place for the other 2 nights, just so that I could have us be 45 minutes closer to my best friend’s resort. Let’s remember: a lot of kids don’t like change. This move was traumatic for Z, who really just started melting down the night of the move and didn’t stop until we got home. Plus it was a ton of work for us packing everything up and transporting it! Stupid, stupid, stupid.
  • Forgot that in the end, when traveling with young kids, it isn’t really much of a “vacation” for you. I mean, it was fun, don’t get me wrong. But it’s a lot of work. It isn’t like relaxing poolside with a margarita when you were in your 20s. You’re gonna work. So just keep that in mind! I felt like I needed a day back home to recuperate!

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