I've Bean Travelling

Greetings, friends! We just returned from our first trip of 2025, a one week visit to Maui. I booked this travel in autumn 2024 before all the political turmoil, so we opted to go ahead with the trip, but it will probably be our last time crossing the US border for a long while.

We had an adventure navigating travel with our newly minted toddler. Teddy is now 19 months and a full fledged wild guy who is constantly on the move and discovering his sense of personal agency, having recently mastered the word “no”!

Toddler antics on the plane

The flight to Hawaii from Toronto is incredibly long with no direct options so we decided to split the flight into two legs. We flew via Porter Airlines from YYZ to SFO and spent one night at The Westin San Francisco Airport before travelling onward to OGG the next morning via Hawaiian Air.

Both flights were okay overall but we did have to deal with Teddy having an extreme, on the floor kicking and screaming, meltdown as we were boarding in SFO. I made the mistake of thinking he wouldn’t need the baby carrier and could just walk down the gate with me, but he wasn’t having it so I had to carry him flailing and wailing while juggling our boarding passes and bags. Fortunately he calmed down once we got to our seats and promptly passed out for a long nap as we took off.

On the advice of various family travel bloggers, I packed a large selection of “plane activities” including stickers, crayons, and books but these actually only entertained Teddy for about 10 minutes. He was more interested in messing around with the safety manual and menu.

Ultimately, the two activities that kept him occupied were lots and lots of snacks (fruit bars and cheese puffs), and watching Thomas and Friends on the iPad. My tip for parents travelling with toddlers is to be flexible about all your “good parenting” rules and routines. Desperate times call for unlimited cheese puffs and screen time.

Arrival in Maui

We landed at OGG around noon and picked up our rental car from Alamo, which I booked through Costco Travel.

After a stop at Walmart for diapers and snacks, we headed to the Hyatt Regency Maui Resort in Kaanapali, where we would be staying for the week.

I was attending a conference for a portion of this trip so we were able to book a reduced rate for an ocean view room, which was Teddy approved. This resort is great for families and kept us well entertained with the kiddie pool, beach access, and proximity to lots of restaurants at Whalers Village.

The resort also houses several resident animals including three African penguins and a few exotic birds. Teddy’s most recent obsession is birdwatching so we had to go see the “duck ducks” everyday.

A week of island fun

I used ChatGPT for the first time while planning our itinerary, and I have to stay it worked pretty well! My prompt was something along the lines of, “Design an itinerary for a 1 week trip in Maui with a toddler staying at Hyatt Regency Maui Resort” and the magic of AI generated a detailed list of suitable activities for us. However, it wasn’t very good at giving food ideas since it kept suggesting that we eat at the same hotel restaurant everyday.

We did use the activity ideas and had a wonderful week of fun around the island with Teddy and our family friends. I will write in more detail about everything we did in upcoming posts, but for now here’s a preview of our time in Maui paradise.