Aloha Reader,

Our first Hawaii trip with kids was planned within an inch of its life.

I had a spreadsheet. Color coded. Every restaurant researched, every activity slotted into a time block, every drive timed out to the minute. I was so proud of that itinerary. We were going to see everything.

We saw a lot of things. We also spent half the trip rushing between them. Someone was always hungry at the wrong time or tired at the wrong moment and the whole day would unravel because we were already supposed to be somewhere else. By day four I was more stressed than I'd been at work.

If I were planning our first Hawaii trip today, here's what I'd do differently.

I'd pick one island and stay there. The urge to island hop on a first trip is strong. You're spending all this money to get there and you want to see as much as possible. I understand it. But moving between islands eats time, adds logistics, and means you never really settle into a place. One island done well beats two islands done rushed every single time. I wish someone had told me that firmly before we booked.

I'd build more nothing into the schedule. Hawaii has a way of surprising you if you leave room for it. The best moments from our early trips weren't the things I planned. They were the shave ice stand we stumbled on, the sea turtles that showed up at the beach while we were just sitting there, the afternoon we scrapped the plan entirely and spent three hours in the hotel pool because the kids were having the time of their lives. You can't schedule those. You can only leave room for them.

I'd stop trying to eat at every famous restaurant. Food is a big part of Hawaii and I love it. But we spent real time and energy chasing reservations on our early trips that honestly weren't always worth it. The plate lunch from the roadside spot we almost drove past was better than two of the fancy dinners we'd planned weeks in advance.

I'd book the big things early and hold everything else loosely. Luau, helicopter tour, Hanauma Bay reservation if you're doing Oahu...lock those in before you leave. Everything else can be figured out when you're there. The families who struggle most in Hawaii are the ones who either booked nothing or tried to book everything.

And I'd talk to someone who'd done it before. Not read ten blogs. Actually talk to someone. The difference between a good Hawaii trip and a great one is usually a handful of specific decisions (which part of the island to stay on, which tours are worth it for your kids' ages, what to skip entirely). Those aren't things you find easily in a Google search.

That last one is basically why I do consultations. In 60 or 90 minutes we can cover your specific trip (your islands, your kids, your budget) and you'll leave with a plan that actually makes sense for your family instead of a color-coded spreadsheet that falls apart by day two.

If you want to grab a spot before summer fills up my calendar, here's where to book.

​Book a Consultation →​

Talk soon,

Marcie