Hawaii Travel Podcast: Hawaii Travel Tips & Things to Do in Hawaii for Your Hawaii Vacation Planning | Hawaii’s Best Travel

200 Episodes Later: 7 Things I Wish I Knew Before My First Hawaii Trip

• Bryan Murphy — Certified Hawaii Travel Expert & Owner of Hawaii’s Best Travel | Hawaii Travel Podcast • Episode 200

Share episode

What if the biggest mistakes I made in Hawaii weren't about what I did, but how I showed up?

After 200 episodes and 30 trips, I'm sharing seven hard-won lessons that changed how I experience Hawaii and travel everywhere else.

You'll walk away with a clearer sense of what respect really means, why slowing down creates better memories, and how to see Hawaii as more than just a backdrop.

👉In this episode, you will:

  • Understand why Hawaii is a living culture, not just a vacation setting, and how that shifts your entire experience
  • Learn why planning ahead in 2026 protects your trip instead of limiting it
  • Discover how slowing down and exploring beyond Waikiki creates the memories that actually stick

_
Scroll up ⬆️ and hit play now to travel to Hawaii with more awareness, respect, and presence than ever before.

🎧Episodes mentioned :

🤓Chapters:

  • 1:40 Understanding Hawaii as a Living Culture
  • 4:35 The Importance of Respect in Hawaii
  • 7:27 Slowing Down for Better Memories
  • 9:38 Exploring Beyond Waikiki
  • 12:14 The Importance of Planning
  • 13:43 How Haw

Take the Survey

_
👉End of the Year Listener Survey


👉Book Your 1-on-1 Hawaii Travel Consultation


📲Connect

_
This Hawaii travel podcast is for travelers looking to plan a trip to Hawaii. Discover travel tips, itineraries, and traveling tips & hacks with guides to help you explore Hawaii. Whether you’re planning a Hawaii vacation to the islands, dreaming of a Hawaiian getaway, or visiting Honolulu, Maui, Kauai, Oahu, or Big Island we’ll help you travel with aloha.

Edge of the Ocean, Stick Figure (w/ permission)
Ukulele and Chill, Coby G (w/ permission)
Talk Story, Hawaiian Style Band (w/ permission)

200_200 Episodes Later- 7 Things I Wish I Knew Before My First Hawaii Trip


[00:00:00] Bryan Murphy: If I could go back in time and talk to myself before my very first trip to Hawaii, there are seven things I have identified that I would immediately say. These aren't travel hacks. They're not trends, they're real lessons. I learned the hard way after 200 episodes in 30 some trips to Hawaii by talking with locals, Hawaiians experts, and travelers.

[00:00:28] Bryan Murphy: Welcome to Hawaii's. Best of podcast helping you plan an unforgettable trip to Hawaii. Here you get practical tips and UpToDate info of what to know before visiting Hawaii. Aloha. I'm Brian Murphy and I'm the owner of Hawaii's Best and the host of this podcast. Thank you so much for joining me This episode, it's a little bit different for me, it's episode number.

[00:00:48] Bryan Murphy: 200 and since episode one, this podcast has been all about you. It's about giving visitors practical tips to plan an unforgettable trip to Hawaii. And everything you're about to hear comes from real mistakes I made early on and lessons I learned later by listening to locals, culture practitioners and people who actually live in Hawaii.

[00:01:14] Bryan Murphy: So if this is your first trip or even your second or third, I, I know this episode will help you experience Hawaii in a deeper, more meaningful way. Along the way, you'll probably hear some familiar voices if you've been listening to the podcast for some time. And these are honestly some of my favorite guests that I've had on the show.

[00:01:32] Bryan Murphy: So without further ado, here are my seven things I wish I would've known before my first trip to Hawaii.

[00:01:40] Bryan Murphy: Number one, I wish I knew Hawaii as a living culture, not just a backdrop. What I mean by that is, you know, Hawaii is definitely so much more than a theme park. I grew up romanticizing about Hawaii, not knowing if I would actually visit Hawaii.

[00:01:53] Bryan Murphy: It'd always been kind of an aspiration and a dream to visit Hawaii one day. Having gone there over some 30 times, definitely feel fortunate and blessed to have visited as often as we have. But I remember my first few trips I had that initial kind of postcard idea of Hawaii. When I think back about my very first trip to Hawaii, I realized I treated it like a, a setting, kinda like a backdrop for a vacation I had planned in my head for.

[00:02:24] Bryan Murphy: Most of my life, I didn't do anything intentionally wrong, but I showed up with a consumer mindset, you know what? What can I see? What can I do? What can I fit into a week? And that shifted for me after having numerous conversations on this podcast with people who helped me understand Hawaii as a place you step into, not necessarily something that you just use.

[00:02:47] Bryan Murphy: Here's a little bit about what Kahala Sorio or Kaha Nui said about this on a previous episode.

[00:02:53] Kahanuola Solatorio: Don't just look at it as a vacation. Look at it as an educational opportunity. Look at it as a, a responsibility when you come travel to Hawaii especially, but enjoy. Enjoy yourself. Yeah. Soak it all in. Because being in Hawaii is, is a special feeling.

[00:03:07] Kahanuola Solatorio: Hawaii's history is very rich. It's very deeper. Exactly like you said, some people may not even know we have a language, an official language. If you look a little bit deeper, if you take some time to research, go to the Ani Palace, go to historical sites. It's all there for us.

[00:03:23] Bryan Murphy: Another friend on the podcast, Kamaka Peeley, helped me see it even more clearly when he talked about how much meaning is held in the land, in the language itself.

[00:03:33] Bryan Murphy: He explained that even the name Waikiki tells a story.

[00:03:37] Announcement: If we just look at the name. Waikiki and I, that's an important thing in Hawaiian culture are our names. So if you look at Waikiki, why wa I is is freshwater and Kiki is the action of, of spouting like a spring. So Waikiki literally means the spouting springs because.

[00:03:56] Announcement: All throughout the shoreline and up into, which is now all covered by cement. They're all freshwater springs, and that's what provided the wetlands and sourced the wetlands aside from streams that flowed down from the mountain,

[00:04:09] Bryan Murphy: that names in Hawaii aren't random. They carry history in deep meaning. And once I started to understand that, Hawaii stopped feeling like scenery and started feeling like a place with memory and with.

[00:04:21] Bryan Murphy: Purpose with layers with people who were here long before any visitors ever arrived. That one shift alone changed how I moved through Hawaii, how I listened and how I paid attention.

[00:04:35] Bryan Murphy: Number two kind of goes along with number one in that I wish I understood why respect matters so much once you know the history of Hawaii.

[00:04:44] Bryan Murphy: For a long time I thought respect in Hawaii was mostly about etiquette. You know, don't do this. Don't say that. Follow the rules. Take your shoes off when you go into someone's home. You know, all those things are important, but what I didn't understand early on is that respect in Hawaii is rooted in history.

[00:05:04] Bryan Murphy: And I think once you understand that history, the reactions, the boundaries, and the sensitivities start to really make sense. Explained it in a way that really made sense for me.

[00:05:16] Kahanuola Solatorio: It was another sad moment in our history where our culture, our language, our identity was being ripped away from us and being forced upon by another government, and three years later, when they banned the language from being spoken, that was just another dagger to the heart of the Hawaiians because.

[00:05:35] Kahanuola Solatorio: That is our identity as people is a language.

[00:05:37] Bryan Murphy: I think that was a big moment for me. I mean, if you go back and you listen to some of the past episodes, I had kanu on probably about four episodes, three or four episodes, and, uh, I've learned a lot from him. I, I've met with him in person when visiting Oahu, and he's been such a help in helping frame my travels.

[00:05:58] Bryan Murphy: But what I hope to communicate with. You that listened to this podcast as well, and because of that. Things started to reframe. Like why is it such a big deal? And of course this matters, but you know, why does it matter? And then Anella Evans, who is a culture practitioner on the island of Lena, add in another layer that changed how I thought about this.

[00:06:22] Anela Evans: Hawaiian creation stories and genealogies. We come from the land, so AA is encompassing of us as well. So it promotes. A sense of holistic wellbeing and there's no separation. You know, for Kanaka humans to thrive ina has to thrive. Mm-hmm And vice versa. It's a very prevalent lesson in that throughout all of Hawaii, you know, there are very amazing examples of Aloha ina and places where.

[00:06:50] Anela Evans: Those lessons can be learned and can be brought to the forefront. That is the underlying theme and governing factor of a Hawaiian lifestyle.

[00:07:01] Bryan Murphy: And I think when you hear that, you realize respect isn't about being perfect or walking around on eggshells. It's about recognizing that you're stepping into a place.

[00:07:12] Bryan Murphy: Where people are still carrying knowledge and honestly loss. And once I understood that respect, stopped feeling like a rule book, it started feeling like something you offer, not something you're forced into.

[00:07:27] Bryan Murphy: The next thing I wish I knew was slowing down would create better memories. And I've talked about this on the podcast quite a bit.

[00:07:36] Bryan Murphy: That's really one of the biggest mistakes I made in my early trips, was trying or feeling like I had to do everything I had, packed days, packed schedules, and a mental checklist of what I was hoping to complete. And then, you know, getting home from the trip, I was like, I didn't do that. One thing I really wanted to do.

[00:07:55] Bryan Murphy: Getting over that has been a, a huge help. On paper, it looked like a great trip, you know, going into it, but in reality, I was rushed, my family was tired, and I really wasn't present most of the time. What I've learned over time is that Hawaii doesn't reward speed, it rewards space. James Kiko. Owner of B Side Kitchen, one of my favorite local spots on the east side of Oahu said something on the podcast that really stuck with me.

[00:08:24] James Kiko: There's Manana Island, or people call it Rabbit Island right in the bay and you kind of, you feel Hawaii over there versus the manmade beaches in Waikiki and everything like that. You know, I love going to Waikiki some. Our staycations are in Waikiki where we play tourists and my kids love it. There's a swimming pool.

[00:08:42] James Kiko: Yeah, there's a music and it's just an escape from our normal. Day life, yeah. That we used. I can understand that. But real Hawaii is outside of Waikiki. Get in your car, take a cruise around the island and put yourself in those uncomfortable places like going to a restaurant that you feel that all the locals are at, but you know that's where you're gonna find the adventure and find experiences.

[00:09:07] James Kiko: Be bold. Take risk, treat everything like an adventure.

[00:09:10] Bryan Murphy: That idea of cruising instead of rushing really changed how I plan trips. Now, some of my family's favorite memories in Hawaii didn't come from big scheduled experiences. They actually usually don't. They came from slowing down, sitting longer, striking up conversations, taking the long way and saying yes to something unplanned.

[00:09:32] Bryan Murphy: Once I stopped trying to fit Hawaii into a schedule, I started experiencing it more fully.

[00:09:38] Bryan Murphy: Number four is, I wish I knew. Hawaii is more than Waikiki. Hawaii is where a lot of people start, and it makes a lot of sense. It's familiar. It's accessible. And for many first timers, it feels like the easiest entry point into Hawaii.

[00:09:54] Bryan Murphy: There's a lot of options. It's a little bit, uh, cheaper as far as, uh, you know, finding a hotel there. But early on I didn't realize how much of Hawaii, I wasn't seeing when Waikiki was the only reference point I had that perspective. I I was re reminded by it. It shifted quite a while ago, but I think Kamaka Peeley culture practitioner on the island, Oahu explained it in a way that I haven't been able to put my, my finger on, say someone's listening and they, they happen to be staying in Waikiki, say this summer for example.

[00:10:29] Bryan Murphy: What would you want them to know? But I think maybe more importantly, once they're on AHU and in Waikiki, how would you want them to go about their, their trip or their experiences?

[00:10:46] Announcement: Thank you for asking that because I, I, I think that's one thing we always, we would like to share as Hawaiians. One thing is enjoy.

[00:10:54] Announcement: We're not angry in the fact that don't come here, you know, and you stay away. That, that's not my perspective. At least come and enjoy because again, our essence of being Hawaiian is, we're here to share this with you, but at that same time, there's more to Hawaiian culture and Hawaii to the extent that you know, than what is just.

[00:11:14] Announcement: In your face. Mm-hmm. Other, you know, aside from checking out Waikiki, and of course people have their more tourist things they wanna do, I would just highly encourage people, if you're gonna come down here, enjoy yourself, but find ways to learn about the culture and the history and the people and take a step further.

[00:11:32] Announcement: How can you give back? I mean, as Hawaiian, I think all of us here are always finding ways to give back to the land.

[00:11:38] Bryan Murphy: I think what's cool about that is a great reminder that Waikiki isn't the whole story of Hawaii. It's just one chapter, and it's not a criticism of Waikiki, but as an imitation to look beyond it, to explore the neighborhoods, small towns, quieter beaches, and places where daily life is happening.

[00:11:59] Bryan Murphy: I think once you understand that, I know once I understood that my trips really changed, Hawaii felt bigger, more layered, and honestly just more real. And I stopped expecting one place to represent an entire culture.

[00:12:14] Bryan Murphy: The next thing is I wish I knew how much planning matters when booking a trip to Hawaii, and especially in 2026.

[00:12:22] Bryan Murphy: One thing that's changed a lot since our early trips to Hawaii is how much planning actually matters. There was a time when you could just show up, rent a car, figure things out as you went. That's really not reality anymore, especially at popular spots and during busy seasons. Andrew Fers from Chaka Guide has been on the podcast a few times and this is what he had to say about planning a road, Ohana excursion

[00:12:48] Andrew Fowers: planning advance.

[00:12:49] Andrew Fowers: I mean, road to Hana is not something you just kinda wake up and like, oh, let's go do, let's go do the Road to Hana. Right? You really have to plan a little bit in advance there.

[00:12:58] Bryan Murphy: Really that applies to a lot of Hawaii now, especially in 2026. You know, you got reservations, parking permits, timed entries, not because Hawaii wants to make things harder, but because there are real limits to how many people, certain places can support.

[00:13:16] Bryan Murphy: That's just the reality. So what I wish I knew earlier is that planning doesn't take away from the experience. It really helps protect it. When you plan well, you'll be less stressed, more present, and you're not scrambling or disappointed when something is already booked. So good planning isn't about controlling your trip, it's about giving yourself space to really actually enjoy it and be in the moment.

[00:13:43] Bryan Murphy: And number six, I wish I knew Hawaii would change how I travel everywhere. I didn't expect Hawaii to change how I travel in general. I thought the lessons I was learning in Hawaii were specific to those islands, but over time I realized that. That mindset kind of followed me everywhere, listening more, slowing down, paying attention to where I am instead of what I'm trying to get out of a place.

[00:14:11] Bryan Murphy: Those habits didn't stay in Hawaii, and I think Kamaka Diaz, he was a past guest on the podcast, shared something that really helped me name this shift a little bit, because for

[00:14:23] Kamaka Dias: the first time in my life I was a howle. I was a howle living in another country. I was trying to dress like them, speak like them, eat like them.

[00:14:33] Kamaka Dias: And to me, I was doing it out of respect. But when I reflected on that and I thought back of my life here in Hawaii, I would always get upset at people doing that. People coming here in their matching aloha shirts with their family and saying Malo and aloha. Saying words poorly, pronouncing them poorly.

[00:14:53] Kamaka Dias: And I would get annoyed by that. And then I, I realized, wow, I, I'm doing the same thing, Madagascar. And I'm not doing it to be disrespectful. I'm doing it as a sign of respect. That really shifted my mindset and gave me a, a new perspective and a little bit more empathy for the people coming here.

[00:15:10] Bryan Murphy: That idea really resonated with me because once you've experienced what it's like to be the outsider, to be the visitor, it changes how you move through places you visit.

[00:15:20] Bryan Murphy: You stop assuming access, you stop centering on what your plans are. You, you go into a spot more humble. Hawaii taught me that good travel starts with humility, honestly. And once you learn that, it's hard to unlearn it in anywhere else. And finally, number seven.

[00:15:40] Bryan Murphy: I wish I knew Hawaii would mean more to me than just a trip.

[00:15:44] Bryan Murphy: What I mean by that is when I first came to Hawaii, it was just a trip. I was excited. It was a destination, something. I was just so pumped, so excited to experience, and then kind of just check it off the box and move on. I didn't expect it to stay with me for so long after 30 some trips and you know, almost 25 years of traveling to Hawaii.

[00:16:08] Bryan Murphy: Over time and through conversations on this podcast, Hawaii stopped feeling like a place I visited and started feeling like a place that has shaped me honestly is how I travel, how I listen, how I think about being a guest in someone else's home. Kahani said something that I think really captures this.

[00:16:28] Kahanuola Solatorio: Don't just look at it as a vacation. Look at it as an educational opportunity. Look at it as a, a responsibility when you come travel to Hawaii especially, but enjoy, enjoy yourself. Soak it all in, because being in Hawaii is, is a special feeling. You know,

[00:16:43] Bryan Murphy: that lion really struck me because it puts the responsibility back on the visitor.

[00:16:47] Bryan Murphy: Not to be perfect, but just to simply be intentional. Then Anella Evans added something that felt like really the, the crux, the heart of it. And I know we've talked a lot about those things, but maybe if we had to boil it down to like one or two things just prior to someone boarding the plane, what would you want them to know?

[00:17:08] Anela Evans: Well, I'd ask them to come to Hawaii with an open mind and with the mindset that is willing to learn new ideas, new concepts, new values. And really allowing oneself to be receptive mm-hmm. To what life here is all about. And I definitely ask that people try to leave as. Little as a footprint as possible, and if you did indeed learn from Hawaii, then to take it home with you and share with others what you learned.

[00:17:46] Bryan Murphy: That's when Hawaii stopped being just a trip for me. It became a relationship. One built on listening, learning, and coming back with more awareness than the last time.

[00:17:58] Bryan Murphy: Honestly, that's why this podcast still exists 200 episodes later. If there's really one thing I think, you know, one thing I hope you take away from this episode, it's this Hawaii doesn't ask you to be perfect.

[00:18:12] Bryan Murphy: It asks. You to be present, to listen to slow down. I think that's why you booked the trip. You want to slow down. You want to soak in the culture and to remember that you're stepping into a place that means something to the people who call it home. Everything I shared today came from learning. I, I called, you know, the hard way.

[00:18:33] Bryan Murphy: It just, it just took a lot more time than I wish it would have. And from those mistakes, from the conversations, from being willing to say, I didn't know this before, but now I know. And if this is your first trip to Hawaii, I hope these seven things help you show up differently. And if you've been before, maybe they help you see it with a set of fresh eyes.

[00:18:55] Bryan Murphy: And if you ever listen to episode one of this podcast. Thank you so much. I haven't even listed back to episode one. And just for final, I'll drop it in the show notes below a link to the very first episode of this podcast. One of the tips I have, 'cause I also produce podcasts for hundreds of other, um, podcasters.

[00:19:16] Bryan Murphy: That's kind of like my day job. One thing if you're thinking about starting a podcast is just get those first 20 or so episodes up. Don't listen. Don't go back and listen to 'em yet. Just get 'em up there and keep going because I know if you're thinking about starting a podcast, you got something important to say.

[00:19:35] Bryan Murphy: And if this episode or this podcast in general. You've ever found any value in it, I would simply just ask for you to leave an honest rating and review. If you're listening on Apple Podcasts or Spotify, that really helps other people who love Hawaii, I think just as much as you find this show. Thanks again for listening, and until next time, as always.

[00:19:57] Bryan Murphy: Live with Aloha

[00:20:03] Bryan Murphy: Mala for listening to this episode of Hawaii's. Best to stay up to date on future episodes. Hit follow on your podcast app. Hawaii's Best is a production of shore break media group with editing by easy podcast solutions and music courtesy of our friends. Stick figure.


Head Shot

Bryan Murphy

Host
Contributor

Shorebreak Media Group

Producer