Aloha Reader,

People assume that after 40-plus trips to Hawaii I sit down and a perfect itinerary just appears. It does not. I still work through the same set of questions every single time, in the same order, because skipping any of them is how you end up with a plan that looks great on paper and falls apart on day two.

Here's exactly how I build a Hawaii itinerary from scratch.

Start with the island, not the activities. This is where most families go wrong. They find a cool snorkel tour or a restaurant they want to try and start building around it. The island decision should come first and it should be driven by your family's profile (ages of your kids, how many times you've been, what kind of trip you actually want, how much driving you're willing to do). Everything else flows from that.

Decide which side of the island you're basing yourself on. Every major island has distinct sides with different weather, different vibes, and different access to activities. On Maui that's the difference between Ka'anapali and Wailea. On the Big Island it's Kona versus Hilo. Getting this wrong means spending a significant chunk of your trip in the car. I spend real time on this decision before I do anything else.

Lock in your anchors first. I call these the non-negotiables: the luau, the helicopter tour, the Hanauma Bay reservation, the Road to Hana day, whatever your family's version of that is. These are the things that book out fastest and have the least flexibility once you're on the ground. Get them on the calendar before you touch anything else.

Build your days around those anchors, not the other way around. Once the big things are placed, the rest of the days take shape naturally. A helicopter tour day is a half day after. A luau night means a slower morning. A full Road to Hana day means nothing else on that day, full stop. The itinerary starts to write itself once the anchors are in.

Plan your first day and last day specifically. First days are almost always slower than people expect. The time change hits, you need to get your car and groceries sorted, everyone needs to decompress. Building in a light first day is one of the most underrated things you can do for a Hawaii trip. Last days need buffer before a flight. I see families schedule activities the morning of a departure and then spend the whole time stressed about making it to the airport.

Leave at least one full unscheduled day. I know this feels counterintuitive when you're spending this much money. But the best Hawaii moments tend to happen when you're not rushing to the next thing. A beach you weren't expecting. A food truck that's inexplicably the best meal of the trip. Give yourself room to find those.

That process sounds straightforward written out like this. In practice the decisions compound fast (especially once you're factoring in kids' ages, trip length, budget, and the hundred small questions that come up along the way).

If you've already got a rough plan but want someone to look it over and flag anything that could cause problems, that's exactly what my itinerary review is for. You send me your day-by-day, I review it within 48 hours and send back comments and suggestions. It's $50 and has saved a lot of families from some genuinely avoidable headaches.

​Submit Your Itinerary for Review →​

If you're earlier in the process and want to build the whole thing together, a consultation is the better fit. We get on the phone for 60 or 90 minutes, talk through your specific trip, and you walk away with a plan that actually makes sense for your family.

​Book a Consultation →​

Either way, summer is filling up fast. If Hawaii is on your calendar, now is the time to get the plan locked in.

Talk soon,

Marcie