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....

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...

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...