Hi, I’m Tom — and here’s why I built this

Here’s the moment that started all this. September 2018, I was on Lānaʻi with a tour group, up on the bluff above Hulopoʻe Bay. I spotted boats lingering offshore, zoomed in with my phone, and watched a single enormous fluke rise clear out of the water. It floored me — my first whale, and even from that far I could feel how big it was.

For years I told that as “the time I saw a humpback in Hawaiʻi.” Then I started building this site — and learned humpbacks aren’t even here in September. They’re 2,500 miles north, feeding off Alaska, and don’t show up until November. Whatever I saw, it wasn’t the humpback I’d assumed.

That gap — between what I was sure I saw and what the data actually allows — is the whole reason this site exists. I stopped trusting one vivid memory, and started trusting the record.

So I ran my usual weather-first playbook over 5 years of Maui data and turned it into straight GO / RISK / SKIP answers — none of that mushy “Maui is great year-round!” non-answer, just the real odds with the numbers sitting right next to them. The whole point: help you spend your few precious days off on a great trip, not a soggy one.

Maui’s first. If you like it, more islands are coming.

If you take just one thing from this whole site, make it this: before you book an island trip, check the weather odds for your dates. That’s it. Everything else here is just me helping you do exactly that —

• A real opinion. Not “it depends” — an actual call, every month, every activity.
• The receipts. Every call shows the historical numbers and the bar I used, so you can overrule me.
• No fake certainty. These are odds from history, not a forecast — and I’ll always say so.

It’s for someone deciding which month to book a Maui trip. It’s not a daily forecast, and it won’t replace Surfline for surfers or a marine forecast for divers. For trip timing, though, I think it beats any listicle out there.