Which Hawaiian Island Is Right for You?

Which Hawaiian island should you pick when every island looks tempting?

The answer isn't which island is "best," it's which one actually fits the trip you're trying to take right now.

👉 Hit play now to get one simple question for each island, Oahu, Maui, Kauai, and the Big Island, that makes the decision easy.

If you've ever stared at Hawaii's four main islands and felt stuck picking just one, this episode is for you.

I'll walk you through what makes each island different so you can stop guessing and start planning.

In this episode of Hawaii's Best, we break down Oahu, Maui, Kauai, and the Big Island one at a time so you can match the island to your trip instead of the other way around.

👉In this episode, you will:

• Learn why Oahu gives you the most options with the least stress
• Find out why Maui feels like the classic Hawaii vacation, even though it usually costs more
• Decide if Kauai's slower pace or the Big Island's spread-out scenery fits your trip better

_
Scroll up ⬆️ and hit play now to finally know which Hawaiian island is right for you.

🤙Resources mentioned:

• Hawaii Island Quiz
• North Shore Huakai Shuttle 
• Hawaii Trip Cost Calculator

🎧 Related episodes:

• Oahu Travel Guide
• Maui Travel Guide
• Kauai Travel Guide
• Big Island Travel Guide

_
💻 Related blog posts:

• Maui vs Kauai (quiz Included)
• Oahu vs Maui (quiz Included)
• Oahu vs Kauai
• Island Hopping Guide

_
🤓 Chapters:

• 1:31 North Shore Shuttle Update
• 2:49 One Island Rule
• 4:03 Oahu Most Options
• 6:29 Maui Classic Vacation
• 8:43 Kauai True Getaway
• 12:21 Big Island Surprises
• 15:24 Quick Island Recap

_
👉 Schedule a Hawaii Planning Session with Bryan

About Your Host: Bryan Murphy is the founder of Hawaii’s Best Travel & a Certified Hawaii Destination Expert through the Hawaii Tourism Authority, since 2020. An HVCB member since 2019, he helps first-time & repeat visitors plan respectful Hawaii vacations w/ clear, practical advice & cultural insight.

📲 Connect on Instagram
🌺 Hawaii Planning Facebook Group
✉️ Free Hawaii travel tips & guides at hawaiisbesttravel.com

🤝 To sponsor the show visit hawaiisbesttravel.com/partner

Hawaii travel podcast helps you plan a trip to Hawaii with clarity. Discover practical travel tips, island itineraries, & local insight to help you explore Oahu, Maui, Kauai, the Big Island.

Edge of the Ocean (w/ permission)
Ukulele and Chill (w/ permission)
Talk Story (w/ permission)

Transcript

244_Which Hawaiian Island Is Right for You?

[00:00:00] Bryan Murphy: Every island in Hawaii is uniquely special. I think we can all agree on that and that's what makes choosing one island so difficult. Oahu, Maui, Hawaii, and the big island, Hawaii Island are not four versions of the same vacation. So today I'm giving you one simple question for each island to help you figure out which one fits your trip.

[00:00:28] Bryan Murphy: Aloha and welcome to Hawaii's best on Brian Murphy. Hawaii destination expert and your personal guide to planning an unforgettable trip to Hawaii. Today we're answering one of the biggest questions in all of Hawaii planning questions. You know, which island should you visit? I, I don't think the best question is which one is best.

[00:00:50] Bryan Murphy: I think the better question is which island fits the kind of trip that you actually want. Maybe if you've been to Hawaii before this time around, what type of trip are you hoping for? The island I'd recommend for your first trip may be totally different from the one I recommend for your honeymoon, your babymoon, your family vacation or your slower, quieter getaway.

[00:01:13] Bryan Murphy: That really does matter the type of trip that you're wanting. So think of this episode as like your starting point. Yeah, I'll give you a clear take on each island and if one grabs you or speaks to you, I have a full guide, a companion guide for each of the islands and all of that will be linked below.

[00:01:31] Bryan Murphy: But quick news, this is pretty cool. I already announced it about a week ago. If you're visiting Oahu anytime soon, it's a new 90-day pilot show called North Shore Huakai and recently was launched on Oahu and it's running from Waikiki and Koolina, the two biggest resort areas on the island. And it runs up to the north shore, runs up to Wayalua and Halaiva and it's just a $5 round trip.

[00:01:56] Bryan Murphy: So the ride to shuttle back to either Waikiki or Koolina, you need to show proof that you bought something that you participated in one of the North Shore businesses and I think that's really easy to do. Anyone going up to the North Shore is probably gonna be stopping off and getting something to eat or just doing some shopping.

[00:02:14] Bryan Murphy: So I actually like that rule. I don't think it's like a, a bait and switch. It's really what this pilot program is designed to do. It's not just a cheap ride. It's built to give visitors spending money with local businesses, especially since they're still recovering from the March Kona low storms that just wrecked havoc over in that area.

[00:02:32] Bryan Murphy: But seats are limited. I've got a full breakdown in booking links and the show notes below. Be sure to check that out. And if you're still not sure which island fits you, I put together a Hawaii Island matcher quiz that you can go ahead and take after this episode or by going to Hawaii's best travel.com/islandquiz.

[00:02:49] Bryan Murphy: Okay, so before we talk islands, here's my one rule. For most trips of say like a week or less, just choose one island. I know, I know island hopping that may have even popped in your head as I was going through the intro, like choosing one island. Why don't you just do them all? I know that island hopping it can sound like a dream and if you have a longer trip, it can work.

[00:03:13] Bryan Murphy: But if you only have like five, six or seven nights, moving islands usually cost you more than it gives you back. So you gotta pack, you gotta check out, you gotta drive to the airport, return the rental car, wait, fly, get another rental car and check in somewhere else. And if you're doing that with family, you could just multiply that by 10 because it just complicates things even more.

[00:03:34] Bryan Murphy: So by the time that you're done with all that, you've lost a big chunk of a precious vacation day. So for a week or less, I usually say like pick one island and go deeper. If you're traveling as a couple, you might be able to do two islands if you're staying a week. So for a week or less, pick one island and go deeper on that island.

[00:03:55] Bryan Murphy: And if you have 10 nights or more, that's when a second island I think really starts to make sense. Okay, let's talk specifically about the islands. The question for Oahu that I wanna leave you with is do you want the most options with the least stress? Oahu receives more visitors than any other Hawaiian island.

[00:04:15] Bryan Murphy: In 2025, about 5.7 million people spent their time on Oahu. And there's a huge obvious reason for that. Oahu has the most flights, the most hotels, restaurant options, tours and visitor infrastructure than any of the other islands. You stay in Waikiki and you've got beach food shopping and tours all close by.

[00:04:37] Bryan Murphy: You may not even need to rent a car in Waikiki. Waikiki is busy, it's touristy, yes, and I won't pretend otherwise, but it's, it's also genuinely convenient. My wife and I, we've stayed in Waikiki just her and I a few times and we really like that option of just not having to rent a car and just bumming around town while we're there.

[00:04:58] Bryan Murphy: The food scene is strong, lot of options. And for our first trip, there's something nice about just, you know, walking to breakfast or going to the beach, watching the sunset right there in Waikiki. But Oahu is not only Waikiki, that's the mistake I don't want you to, to make because that can confuse a lot of people.

[00:05:17] Bryan Murphy: Allie and I found this out on a trip when we were staying at the Kahala, which is outside of Waikiki. So we wanted somewhere local for dinner, not just the closest hotel restaurant and Allie found this place called Beachside Kitchen. I've talked to them before on the podcast and we've had them on the podcast, but we found them on Yelp and it turned out to be one of those really cool moments and memories that kind of has stuck with us.

[00:05:41] Bryan Murphy: And it was nothing fancy, but it was just good local food, super warm, super inviting. So shout out to Beaside, check them out if you're staying on Oahu. But that's what Oahu does really well. You can have the easy hotel and beach trip. You can also find local spots, the North Shore, like we mentioned, Windward, Oahu over on the east side and neighborhoods that feel completely different from where you started that morning.

[00:06:09] Bryan Murphy: So if you want variety, easier logistics and the most flexibility, Oahu is really the hardest island to get wrong. It's honestly my favorite island. It's got all the sides are unique and have their own personality, which I really love. So I'll, I'm gonna link my Oahu travel guide below in the show notes.

[00:06:29] Bryan Murphy: So let's go ahead and let's hop over to Maui. The question for Maui that I would wanna leave you with is, do you want the classic Hawaii vacation and are you willing to pay more for it? So Maui was the second most visited island in 2025 and that was about 2.5 million visitors visited Maui. For a lot of travelers, Maui is what they picture when they think of Hawaii.

[00:06:55] Bryan Murphy: You know, you got resort beaches, sunset dinners, whale watching season, Haleakala. It's a strong fit for honeymoon's anniversaries. We did, we've done a anniversary over there on Maui. It was great. It's great also for families who want beach time mixed with a few big experiences. But here's where I'd be careful about Maui.

[00:07:16] Bryan Murphy: Don't plan Maui like a checklist. The Rhoda Hona, for example, is one of those most, you know, famous drives in Hawaii, if not the world, but if you rush it, it turns more stressful than memorable and it's like, "How did I get... I feel stuck." You feel like you have to go all the way to Hana. No, you don't have to go all the way to the town of Hannah.

[00:07:36] Bryan Murphy: That is a very long day. Some people should drive it themselves, others enjoy it more with a guided local tour. That's what I usually recommend for a first timer. So same idea with Jalekola Sunrise. It can be incredible, but you do need reservations so you don't wanna leave that for the night before. And if whales are on your list of must seas, Maui is one of the best islands for that and you have peak season generally from January through March.

[00:08:05] Bryan Murphy: Now really the honest part, and I've already said it, Maui tends to run more expensive than Oahu, really than any of the other islands. Hotels, rental cars, food and activities add up really fast. Recent hotel averages have been running around $500 plus a night in, you know, higher travel periods and obviously we've seen it more than that, but that's just kind of the average though that shifts by season and property and side of the island and, and et cetera.

[00:08:32] Bryan Murphy: So be sure to price out the full trip prior to arriving or prior to your planning. I have a trip calculator that I will include in the show notes as well. All right now we're gonn go ahead and island hop over to Kawaii and, and the one question that I would wanna pose for you would be, do you want to feel like you actually got away?

[00:08:53] Bryan Murphy: Like you actually went on vacation. Really, that's where Kawhi delivers. It's called the Garden Island. It really fits. It's green, it's dramatic, it's a lot slower and it's less built up than Oahu and Maui. No building is above a coconut tree is kind of the, the law there. And in 2025 it had about 1.4 million visitors.

[00:09:17] Bryan Murphy: So the biggest thing I would tell you about Kawaii is you have to move with the pace of the island. If you show up, you know, still in like mainland mode, especially if you're coming from the West Coast or LA SoCal area, trying to force every hour and control every plan, you're going to have a rough time.

[00:09:38] Bryan Murphy: The roads are slower, the weather shifts, the North Shore gets rain and dinner spots may close earlier than you expect. There's really no night life scene. I, I should go back and mention Waikiki has probably, if you're looking for that like nightlife, Waikiki has that. Kawhi definitely does not have that.

[00:09:58] Bryan Murphy: Kwai really rewards those who base their time with the sun. They get up with the sun and they start to slow down when the sun goes down. But if you let the island set the pace, it can be one of the most meaningful trips you can take. We love to, especially when our girls are getting older, we have three girls, couple are in high school now and we love the pace of Kawaii.

[00:10:21] Bryan Murphy: We still really love Oahu, but we love the pace of Kawaii and just the views are just incredible on that island. Nepali Coast is like that postcard image is huge. Sea cliffs, deep valleys, ocean views, barely looks real. It's just like postcard. Waimea Canyon is also really cool. It's called the Grand Canyon of the Pacific and honestly it fits that name.

[00:10:44] Bryan Murphy: I remember my first time going up to the Waimea Canyon lookout and kind of leaves you in awe. Not as much as the Grand Canyon. I remember my first time going to the Grand Canyon and you just kind of takes your breath away a little bit. Waimea Canyon definitely does do that to some extent as well. But a huge portion of Kawhi isn't reachable by road at, at all.

[00:11:05] Bryan Murphy: It's, which is part of what makes it feel kind of wild and, and protected. A lot of places you can only reach by boat or by helicopter. Like if you wanna tour the Nepali coast, I would recommend doing like a boat tour. A lot of people do helicopter tours, so that can be kinda controversial. I'm not a expert on the safety of helicopters, but I'll leave that up to you and, and what you wanna do.

[00:11:29] Bryan Murphy: But this is one of the most popular places in Hawaii to do helicopter tours and to do boat tours the Nepali coast is really the only way to go to see it. One planning note as far as reservations go when you're visiting Kawaiiana State Park or the Kalal Trail area for non-residents need advanced reservation.

[00:11:51] Bryan Murphy: So don't assume you can just show up and do that. Also, the lighthouse, the Kilauea Lighthouse needs advanced reservations as well. So if you want scenery, quiet, hiking, and a real sense of just getting away, Kawhi is really hard to beat. And if you want that nightlife shopping and easiest logistics, it's probably not your island, but honestly, that's why I love Kawaii as well.

[00:12:17] Bryan Murphy: So I'll link my Kawaii travel guide below in the show notes. All right last but certainly not least the Big Island, Hawaii Island are now officially just Hawaii. The question for the Big Island is do you want a trip that keeps surprising you? And let me kind of unpack with what I mean by that. In 2025, about 1.75 million visitors spent time on the Big Island.

[00:12:45] Bryan Murphy: So that's fewer than Oahu and Maui, but the island itself is bigger than all the other main islands combined. That means longer drives and planning by region instead of by what looks close on a map. We spent Christmas on the big island a couple years ago and it was a great fit for the trip. It wasn't busy.

[00:13:06] Bryan Murphy: I thought it'd be a lot more busy or especially going during Christmas break, but maybe we just got lucky, but it was really nice. I felt more spread out, a little bit more rugged, a little less touristy, but still there's resort areas as well. You can get out of those areas pretty quickly and really we just loved our time on the big island.

[00:13:27] Bryan Murphy: That size is, is the whole appeal being spread out. You've got the sunnier side of the island, which is the Kona coast, beaches, you have lava fields, rainforest near Hilo, high elevation areas around Montecaya and Mona Loa. You also got black sand beaches, coffee farms, amazing. We went to a coffee plantation, did a tour.

[00:13:48] Bryan Murphy: It was so good. Obviously, you have Hawaii Volcanoes National Park. Just briefly about the volcano, Kilauea and its activity that's been happening for about two years now. Volcano activity can shift quickly in either direction. So don't plan your whole trip around seeing active lava. Plan around Hawaii Volcano's National Park because it's worth visiting either way if there's active lava flow or if there's not.

[00:14:15] Bryan Murphy: To get up to date on that, you can just check Hawaii Volcano Observatory close to your travel dates. Also, the National Park website is a great place to go for up-to-date info because it changes sometimes on the daily. A few other things to know about, some of the best things to do. Manare night snorkeling off Kona is one of the most incredible ex - ocean experiences in Hawaii.

[00:14:39] Bryan Murphy: And also Punolu Black Sand Beach is another great stop. Just give Vijunu the sea turtles plenty of space if you happen to spot them there, which you might, which you probably will. Also, another thing to remember about the Big Island is you need a rental car. I didn't mention that for the other islands.

[00:14:57] Bryan Murphy: You do, except for Oahu, if you're staying like in Waikiki, you probably don't need a rental car. I mentioned that. But on Kawai on Maui and especially the big island, you definitely need a rental car that's something you wanna get as early as possible. Really a car isn't optional and the island is just too spread out to just wing it and try to like get Ubered across the island, which can take an hour and a half.

[00:15:24] Bryan Murphy: So really it comes down to this. If you want the most options with the least amount of stress, choose Oahu. If you want the classic Hawaii vacation and you're okay paying a little bit more for it, then Maui is your island. If you wanna feel like you actually got away, choose Kawaii. And if you want a trip that's a little bit spread out and has some dramatic scenery, Big Island is for you.

[00:15:48] Bryan Murphy: But if you're still stuck, you want a little bit more guidance, take the island matcher quiz at Hawaii'sbesttravel.com/islandquiz and then go listen to the full guide of whichever island, uh, you land on. I'll link that all below. All right, well, thanks for making it all the way to the end of this episode.

[00:16:07] Bryan Murphy: If it helped you plan for your trip, I would just humbly ask you to go ahead and hit follow on your podcast app if you're listening on Apple or Spotify. All right? So until next time, as always, live with Aloha. Mohala for listening to Hawaii's best. If you found today's episode helpful, make sure to hit follow on your podcast app so you don't miss future episodes.

[00:16:29] Bryan Murphy: You can find all links and resources mentioned today in the show notes below. Hoye's best is produced by Shorebreak Media Group, edited by Easy Podcast Solutions and with music by our friends, Stick Figure.