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 the same buffer you would for any domestic flight and you'll be fine.

A few other things worth knowing before you book.

There are three airlines operating inter-island right now. Hawaiian Airlines has the most routes and the most frequency (roughly 170 daily flights connecting the main islands). They just joined the Oneworld Alliance this month, which means HawaiianMiles now earn across Alaska, American, Qantas, and a dozen other partners. If you travel internationally at all, that changes the math on which loyalty program is worth building.

Southwest flies the same major routes at competitive prices and their no-change-fee policy is genuinely useful when you're planning a family trip and things shift. One thing to know: Southwest has pulled back on inter-island capacity over the past year, so some routes connect through Honolulu rather than flying direct. Still worth checking, especially if price flexibility matters to you. And their two free checked bags applies to inter-island flights, which for a family hauling beach gear can save real money.

Mokulele Airlines is the third option and most visitors don't know it exists. They fly small nine-seat planes to airports the big carriers skip entirely (Hana on Maui, Kapalua on the west side of Maui, Molokai, Lanai). If getting into Hana without the six-hour Road to Hana drive sounds appealing, Mokulele is how you do it.

A few things that add up fast on multi-island trips that I wish someone had told me earlier.

You need a separate car rental on each island. I see families budget for one and forget about the second. If you're doing Oahu and then Maui, that's two separate pickups, two separate costs. Discount Hawaii Car Rental lets you search across islands in one place, which at least makes it easy to compare everything together.

Luggage fees hit you on every flight. We've shifted to packing in soft-sided bags that fit overhead on inter-island legs. It's made the whole moving-between-islands process so much smoother.

And one timing note: Friday afternoons and Sunday evenings are the most expensive inter-island departures because that's when local residents commute. First morning flights are consistently cheaper and the least likely to run late. If you're flexible, that's the window to aim for.

I have a full breakdown on the site covering which island combinations work best for families, how to decide whether island hopping is actually worth it for your trip length, and what each route looks like in practice.

​Read: Island Hopping with Kids — Is It Worth It? →​

Talk soon,

Marcie