Aloha from Oahu! Let's Talk Hawaiian Islands

Usually when I’m talking about choosing between islands, I’m talking about Greece!

But I’m currently on a very different island, so let’s talk about Hawaii.

This is my fourth trip to Hawaii in the last five years, and it has easily become one of my favorite places to travel with my loved ones.

I’m here with family this time, including some young kids, so naturally this trip looks a little different than it would if my husband and I were here on our own. And honestly, that’s part of what I love about Hawaii. There are so many ways to experience it.

Even Oahu alone can feel like three completely different vacations depending on where you stay.

Which brings me to something I say about the Greek Islands all the time: the islands are not interchangeable.

You can’t just ask, “Which Hawaiian island is the best?”

Well, you can. But my annoying travel advisor answer is going to be: What do you actually want to do when you get there?

Because that changes my answer.

Oahu: You can have a little bit of everything

I’m on Oahu right now, staying in Ko Olina, and this trip is very much geared toward the kids in our group.

Ko Olina works really well for that. It’s on the western side of the island, it’s quieter and more resort-focused, and the lagoons make it very easy to spend a day by the water without needing much of a plan.

Three of the major resorts here are Four Seasons Resort Oahu at Ko Olina, Aulani, A Disney Resort & Spa, and Marriott’s Ko Olina Beach Club. If you know anything about me, you can probably guess which one I’m at!

They’re all right here in Ko Olina, but I wouldn’t recommend them to the same traveler.

That’s the part of travel planning I think gets overlooked sometimes. You can choose the “right” destination and still end up with a vacation that doesn’t really fit you because you chose the wrong area or the wrong hotel.

Oahu is a perfect example of that.

Stay in Waikiki and you get a completely different Hawaii experience. It’s busy, energetic and a massive tourist destination, with tons of restaurants and shopping right alongside the beach.

The first time I experienced Waikiki, I felt like I was on Rodeo Drive…but on one of the most famous beaches in the world. You have designer stores, big hotels, restaurants and people everywhere…and Waikiki Beach right in front of you.

If you like having a lot going on around you, that can be really fun!

But if that is not your idea of a relaxing Hawaii vacation, don’t write off Oahu altogether.

There’s also the North Shore, which is much more laid-back and known for its surf culture, beaches and smaller-town feel. And then, of course, you have Ko Olina, where you can settle into more of a quiet resort vacation.

Personally, if you’re coming to Oahu — especially for the first time — I really recommend renting a car for at least part of your stay.

Turo is very popular here (it’s an app-based service where you can rent a car directly from a local), and having a car gives you the freedom to leave whichever area you’re staying in and see more of the island on your own.

If you fly all the way to Oahu and never leave your resort area, I think you’re missing a big part of what makes this island so magical.

Maui: The Hawaii trip you probably have pictured in your head

Maui gives me more of that classic Hawaii vacation feeling.

Beautiful beaches. Gorgeous resorts. Tropical scenery. Plenty of time to relax, but enough to explore when you’re ready to leave your lounge chair.

And then, of course, there’s the Road to Hana.

This isn’t just “drive somewhere, take a picture, drive back.” The drive itself is the experience — winding roads, rainforest, waterfalls and stops along the way.

It’s the kind of day where I would absolutely rather have a plan for what is actually worth stopping for than try to do every single thing someone saved on TikTok.

And if you’re more adventurous, there’s Haleakalā National Park. You can head up to the summit of this massive dormant volcano and hike through a landscape that looks absolutely nothing like the tropical resort areas below.

Just know that this is one of those experiences where doing a little homework beforehand matters. The elevation and weather at the summit are very different from what you’ll experience down at the beach, and depending on what you want to do, you may be starting your day very early.

That combination is what I like about Maui: you can have the beautiful resort vacation and build in some pretty incredible experiences without making the entire trip go-go-go.

Kauai: This is where I’d send my adventurers

Kauai is the one I’d start looking at if you told me:

“I want to hike. I want to kayak. I want to surf. I want stunning scenery. And I don’t need a huge restaurant and shopping scene.”

Now we’re talking!

Kauai is lush, dramatic and generally feels less developed than Oahu or Maui.

You’ve got cliffs, waterfalls, canyons, beaches and greenery everywhere.

And yes, there are absolutely moments when it looks like Jurassic Park…appropriately. 😂

The trade-off for all that green? Rain.

Kauai can be wetter, and if your vacation happiness depends on having perfectly sunny beach weather every single day, that’s something I’d want you to understand before choosing it.

But if you’re the person who is excited to put on hiking shoes, get a little muddy and spend the day exploring?

Kauai may be exactly what you were picturing when you said you wanted to “experience Hawaii.”

Let’s talk about the locals

I have to talk about the hospitality here for a minute, because it’s one of the reasons I love coming back to Hawaii.

From the moment we landed on Oahu this trip, I felt the warmth and welcome from the people here. Our shuttle rep also made sure we had the appropriate car seats for the little ones traveling with us. Our driver told us where to find his favorite poke, coffee and breakfast during our stay and gave us tips on how to support local businesses on the island.

These are the kinds of recommendations and little touches you really only get when you talk to someone who lives here (or your favorite travel planner who’s already talked to the locals 😉).

But my favorite part was when our driver told us about the meaning behind aloha and the shaka, and what tourism means to people who live in Hawaii. He said he wanted us to really experience aloha so we could take it home with us and spread that message after we leave.

I’ve been lucky enough to come back to Hawaii multiple times, and experiences like this are a big part of why I do. Yes, Hawaii is beautiful. Obviously. But the warmth I’ve experienced from the people here is second to none.

It’s also a good reminder to actually talk to people when you travel! Your driver, your server, your guide, the person making your coffee — they can sometimes tell you more about a place than another hour of scrolling through reviews ever will.

So…which Hawaiian island should you choose?

I don’t love answering this question with a simple ranking.

If you tell me you want shopping, restaurants and plenty to do, but your spouse wants beaches and a quieter resort, we can work with that.

If you tell me you want a beautiful resort but you’ll get bored sitting there for seven days, that tells me something, too!

The goal isn’t to choose the Hawaiian island everyone else says is the best.

It’s to choose the one that makes sense for the way you want to spend your vacation.

And sometimes we can get even more specific than that. Oahu alone proves that choosing the island is only part of the decision — Waikiki, the North Shore and Ko Olina can give you three very different trips without ever getting on another plane.

Apparently I just really enjoy matching people with islands. 😂🌺

So tell me: are you Oahu, Maui or Kauai? And if you have absolutely no idea, tell me what your ideal vacation day looks like and I’ll tell you which one I’d start with.