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...
6 days ago • 2 min read
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...
8 days ago • 2 min read
Aloha Reader, My oldest has been to Hawaii about 12 times. At this point he has opinions. On our last Kauai trip he decided he wanted to do a serious acai bowl taste test. Every morning, a new spot. He kept mental notes, compared textures and toppings, took the whole thing very seriously. By the end of the week he had a definitive ranking. Sunrise Coffee won, if you're curious. That trip is a good example of what Kauai does to people who are ready for it. It slows you down in the best way....
13 days ago • 1 min read
Aloha Reader, There is a version of a luau where you sit at a long banquet table under fluorescent lights eating mediocre buffet food while someone on a stage performs a show that feels like it was designed for a convention center. And there is a version where you're sitting outside at sunset, the food is actually good, and your kids are completely captivated by the fire knife dancer. The price difference between those two experiences is sometimes almost nothing. The experience difference is...
20 days ago • 2 min read
Aloha Reader, My youngest and I were sitting at dinner inside Volcano House, the lodge that sits right on the rim of Kilauea caldera, and the lava was glowing through the window behind our food. Not a photo of lava. Not a viewing platform. Dinner. With lava. In the background. I couldn't stop looking at it. Neither could he. At some point we both just put our forks down and stared. That moment is why I think the Big Island is the most underrated island in Hawaii for families. Most people skip...
22 days ago • 1 min read
Aloha Reader, The rental mask fogged up about 90 seconds into our first snorkel at Molokini. My kid pulled it off, declared snorkeling was boring, and spent the rest of the morning throwing rocks on the boat. We tried again two days later with gear that actually fit. She's been asking to go back to Hawaii every year since. I'm not saying rented gear ruined that trip. But fit and visibility matter way more than most people expect, and rental gear is genuinely a mixed bag. Sometimes it's fine....
27 days ago • 2 min read
Aloha Reader, The first time we did an inter-island flight, I treated it like catching a subway. We showed up about 25 minutes before departure, bags in tow, fully relaxed. We made it. But just barely. And I spent the whole walk to the gate sweating through my shirt, which is not the vibe you want at the start of a Hawaii vacation. Inter-island flights are short (Oahu to Maui is about 25 minutes in the air) but the airport experience is completely normal. Security line, gate, boarding. Budget...
29 days ago • 2 min read
Aloha Reader, This is the question I get more than almost any other. Maui or Oahu? Which one should we do? And the answer I always give is: it depends on your family. Not in a wishy-washy way. In a very specific way. Because these two islands are genuinely different trips, and the right one for you has everything to do with what you're actually looking for. So let me walk you through how I think about it. You should probably do Oahu if: It's your first time in Hawaii. Oahu is the easiest...
about 1 month ago • 2 min read
Aloha Reader, I got an email a couple weeks ago from a mom who'd been planning her July Maui trip for months. Flights booked. Hotel sorted. She just hadn't gotten around to the luau yet. She wanted to know which one I'd recommend. I pulled up availability. Sold out. All of them. For her entire week. That's not unusual for summer Hawaii anymore. The window between "I should book that" and "it's gone" has gotten a lot shorter. If you have a trip on the calendar between June and August, some...
about 1 month ago • 1 min read