Why Planning Your 2026 Hawaii Trip Feels Chaotic — And the Simple Fix

Why does planning a Hawaii trip feel like you're drowning in browser tabs and contradictory advice?

Most travelers don't realize how overwhelming Hawaii planning gets until they're second-guessing every decision and comparing endless hotel reviews.

👉Plan your Hawaii trip with Bryan

Hit play now to learn the five most common planning mistakes and the simple fixes that'll make your 2026 trip feel easier and more exciting.

If you've ever wondered how to cut through the noise and build a Hawaii itinerary that actually works for your family, this episode is for you. You'll walk away with a clearer sense of what to focus on and what to skip.

In this episode of Hawaii's Best, Bryan breaks down the top five planning mistakes travelers make so you can avoid stress and enjoy the trip you actually want.

👉In this episode, you will:

• Identify which sources to trust and how to stop information overload before it derails your plans
• Match your itinerary to your family's pace instead of someone else's highlight reel
• Respect cultural boundaries and stick to legal trails that honor Hawaii and its people

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Scroll up ⬆️ and hit play now to plan a Hawaii trip that fits your rhythm and cuts through all the chaos.

👉Start Planning Today!

🤓Chapters:

• 0:57 Understanding Hawaii's Unique Rhythm
• 1:47 Top Mistake #1
• 3:06 Top Mistake #2
• 5:35 Top Mistake #3
• 7:14 Top Mistake #4
• 8:30 Top Mistake #5
• 11:23 The Best Way to Plan Your 2026 Trip

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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)

Chapters

• 0:57 Understanding Hawaii's Unique Rhythm
• 1:47 Top Mistake #1
• 3:06 Top Mistake #2
• 5:35 Top Mistake #3
• 7:14 Top Mistake #4
• 8:30 Top Mistake #5
• 11:23 The Best Way to Plan Your 2026 Trip

Transcript

198_Why Planning Your 2026 Hawaii Trip Feels Chaotic — And the Simple Fix

[00:00:00] Bryan Murphy: If planning your Hawaii trip feels like a mess of tabs, open list and conflicting tips, you're definitely not alone. Most people don't realize how overwhelming Hawaii planning can get until they're in the middle of it. You start with this excitement. You're going to Hawaii. And then you're comparing hotel reviews, reading contradictory advice, and second guessing every decision.

[00:00:24] Bryan Murphy: Today. I'm gonna help you cut through all of that noise on this episode of Hawaii's Best.

[00:00:33] Bryan Murphy: Welcome to Hawaii's. Best of podcast, helping you plan. Unforgettable, Hawaii Vacation with practical tips. My name is Brian and I'm the owner and host of Hawaii's Best Travel. Thank you so much for joining me. If this is your first time welcome. If you've been here for a while, welcome back and if the planning part of your Hawaii trip has felt stressful, you're not alone.

[00:00:55] Bryan Murphy: This episode is for you.

[00:00:57] Bryan Murphy: Hawaii is different than many other destinations. The rhythm is slower, especially if you're coming from the continental us. The logistics are more layered, a bit more complex, and the planning can be a bit trickier, but that doesn't mean you're doing anything wrong with your planning.

[00:01:15] Bryan Murphy: But a few simple shifts can make the whole process feel a lot easier, a lot more exciting, more doable. And today we're gonna help you get that focus. I'm gonna be talking about the top five most common mistakes. I see time and time again people make when planning their trip to Hawaii, especially for the first time.

[00:01:35] Bryan Murphy: These mistakes show up. Almost every conversation I have with travelers and avoiding them makes a huge difference in how your trip feels, not just during the planning phase, but actually once you're in Hawaii.

[00:01:47] Bryan Murphy: So let's start with number one, and that's probably the most common is information overload.

[00:01:53] Bryan Murphy: Most people start planning by opening a bunch of blogs, reels, tiktoks, and those quote perfect itinerary posts. And before long, you're 20 tabs deep and unsure what's actually right for their trip. Second guessing a lot of things. You know, if you got one blog saying you need to spend 10 days on Maui, and another saying three is plenty.

[00:02:17] Bryan Murphy: Someone's raving about it. Hidden Beach, while someone's. Warning, you don't go to that beach. That's not right. You're not supposed to be there. You might get in trouble. The problem isn't a lack of information. It's too much of it, and a lot of it isn't island specific. It's not current, or it isn't realistic for the way most people actually travel.

[00:02:38] Bryan Murphy: And here's a, a simple fix to that is cut down on your sources. Pick a couple of reliable guides or voices that stay current with Hawaii and understand the nuances of each island and build from there. You don't need 50 options, all the tabs. You just need two or three good ones that align with your travel style.

[00:02:58] Bryan Murphy: And honestly, I hope that Hawaii's best myself. We fit your vibe and your style, and we're one of those. Trusted voices for you.

[00:03:06] Bryan Murphy: Mistake number two kind of goes with mistake number one is conflicting advice. You got stuff like, you know you gotta do the road Ohana. No, don't do the Road Ohana. Book everything ahead.

[00:03:16] Bryan Murphy: Just wing it. Skip the luau. The lu I is a must. Whatcha talking about. It's no wonder why people get stuck and feel stuck. And a lot of advice online is based on someone else's travel style. Not specifically your travel style for you and your family. Well, it works for a solo traveler. With no kids, no schedule doesn't necessarily work for a family with young ones who needs to manage the nap.

[00:03:42] Bryan Murphy: Now, what works for someone chasing the venture also doesn't work for someone who wants just to relax and chill. The key is matching your plans to your pace, not someone else's to-do list and someone else's highlight reel someone else's. Itinerary. If you're not a sunrise person, don't plan a 5:00 AM hike just because it's popular just to get the photo.

[00:04:05] Bryan Murphy: If you love structure, don't force yourself to go with the flow because someone said that's the Hawaii way. You just gotta go with the flow. Your trip should fit you and your family. Those are the memories that you're building. That's what really matters. A couple quick fixes is just, it's more of a mindset shift, is just to take a breath and ask yourself those questions.

[00:04:28] Bryan Murphy: What do you and your family want from this trip? Are you wanting to do all the adventure and stuff or are you wanting to pull back you? You want to breathe, you want to break? You can definitely do both, but it's just important to understand what you want for this trip. And some of our trips have been all in everyday booked and planned.

[00:04:48] Bryan Murphy: That's. The rarity for us, honestly, a lot of our trips, we kind of just go with the flow. We have a few things on our list that we each want to do, and we make sure we get those. But ask yourself, what does your family need? What do you need for this trip? Not just to be self-serving, like, I'm just gonna take this trip for myself and I'm not gonna give back.

[00:05:08] Bryan Murphy: Obviously, that's not the intent of that question. The intent is how you plan. How are you gonna plan this trip? As I'm talking, if a lot of this is feeling familiar and if you've been stuck in that loop for, you know, too much information and not enough clarity, these are the exact things that I do help people fix in one-on-one planning sessions, and I'll share a little bit about that later because this is something that I, I just officially launched.

[00:05:32] Bryan Murphy: I'm really excited about it. So maybe it might be helpful for you.

[00:05:35] Bryan Murphy: Number three is unrealistic itineraries. A lot of the sample itinerary days online, they look great on paper, but they really fall apart in real life. A lot of them don't anticipate or include drive times parking, weather, trail closures, and just a general pace of Hawaii aren't factored in.

[00:05:56] Bryan Murphy: And honestly, there's a lot of traffic on Oahu that surprises a lot of people. And most first time visitors, they try to stack too much into a single day. I see itineraries that have, you know, sunrise at Halala, breakfast at Paia, snorkeling at Molokini, lunch in Wale and sunset at a beach on the west side.

[00:06:16] Bryan Murphy: That's not a day, that's like a marathon. That's maybe. Two or three days right there. And the fix for this is pretty simple. Choose one anchor activity for the day. You know, be it a hike, a beach, a major scenic drive, and then build around that. Everything else is a bonus. Maybe you do the hike in the morning and grab lunch nearby.

[00:06:38] Bryan Murphy: Spend the afternoon at a beach close by. And that's really a full day. That's a good day right there. It gives you time to breathe. It gives you time to connect with people as you go about your travel, to connect with locals, you connect with Hawaiians and not just be so rushed getting to the next thing.

[00:06:56] Bryan Murphy: So when you keep your days realistic, the whole trip, it just honestly feels better. You're not rushing, you're not stressed for the most part. Stress does happen. Unexpected things do come up. This happens on vacation, but you actually get to enjoy. Where you are by just choosing one anchor activity for the day.

[00:07:14] Bryan Murphy: Mistake number four is cultural missteps. This usually isn't intentional. I know my first few visits to Hawaii, they, these weren't intentional by any means. It's just lack of understanding or lack of knowledge. Honestly, people just don't know what's off limits sometimes or what's disrespectful or what the local perspective is until they're already there on island.

[00:07:39] Bryan Murphy: Some of the most shared spots online, the ones with millions of views, honestly shouldn't be accessed at all. They're on private land, they're sacred sites, or they've been closed for a while to protect the environment, but because they look beautiful and someone posted about it, visitors often assume.

[00:07:57] Bryan Murphy: It's fine. I saw it at Instagram. The fix is simple. Stick to legal. Maintain trails and beaches. Pay attention to signs. Even if the signs are handwritten, they're there for a reason. If a gate is closed or a sign says kapu, that means forbidden, sacred respect. Keep out. And honestly, when in doubt, choose what honors the place and people who live there.

[00:08:20] Bryan Murphy: It's okay to ask questions that's not just about being a good visitor. It's about protecting Hawaii for future generations. It's something that we're all entrusted with when we visit.

[00:08:30] Bryan Murphy: And number five, probably another big one is trying to make. Everyone happy, especially if you're going with a large group, especially if you're doing a multi-generational trip, which we pretty much always do.

[00:08:40] Bryan Murphy: Families travel at different speeds. Someone wants to hike, someone wants to relax, someone wants to go to the pool, someone wants to go to the beach. Someone wants adventure. Someone just wants to be left alone. And when you try to cram everything in to please everyone, you end up burning a lot of people out and yourself along the way.

[00:08:58] Bryan Murphy: And honestly, usually no one ends up happy. It just becomes like, why are we even here? Those moments. So I've talked to parents who plan every hour, every day to make sure their kids, their spouse and their in-laws all got what they wanted. But by day three, everyone was exhausted and kind of just ripped up the itinerary and like, we just need a break.

[00:09:19] Bryan Murphy: That happens a lot, but the better approach is leave space in your days. You know, think slower mornings, open your afternoons up, build in some downtime, let people split up for an afternoon if they wanna do different things. You can enjoy more, argue less, and everyone gets a little of what they came for.

[00:09:38] Bryan Murphy: One of the questions we always ask our girls, we have three girls, you know, what are your top one to two things you want to do for this trip? So having that ahead of time is important. To know, getting them involved in the planning process and having them understand all this research you've been doing, helping them understand, you know, what are those drive times and, and you know, if, if you're trying to do this all on your own, it can feel overwhelming for sure.

[00:10:03] Bryan Murphy: So getting your family involved with the planning process is definitely encouraged and can help save some of those headaches when you're actually there in Hawaii. All of these mistakes are super common. I see them every week in my dms at Hawaii's best in emails, and none of this means you're doing anything wrong.

[00:10:25] Bryan Murphy: Hawaii has its own rhythm. It's not like you're planning a trip to a city where everything is close and runs on a tight schedule. The islands move slower, and each island has its own pace. Oahu feels completely different than Kauai and vice versa, and the distances are deceptive. You know, we're on island.

[00:10:45] Bryan Murphy: It's small, but you'd be surprised how long it can take to get from Kona over to Hawaii, volcanoes National Park, and the weather can change by the hour. Definitely depends on which side of the island you're on, but when your plan matches that rhythm, your pace, your style, your family, everything feels easier.

[00:11:05] Bryan Murphy: And more enjoyable and. The memories are cherished, I think a bit more sweeter and not like, oh yeah, I remember that. The picture's nice, but remember the fight that we had getting up there because we're running late. It's to help minimize those stressful moments.

[00:11:23] Bryan Murphy: So if you want help building a Hawaii trip that fits your pace, your family's pace, and cuts through all the noise, I now offer one-on-one planning sessions.

[00:11:33] Bryan Murphy: No upsells, no commissions. I don't hand you over to a travel agent. I'm not a travel agent. Just simple, honest guidance that is personalized for you based on what actually works. To take a look at the sessions I offer, you can go to the first link in the show notes below, and if you have a question about that, I give you my personal email at the bottom of that page where you can reach out to me with any of your questions.

[00:11:57] Bryan Murphy: We'll walk through your plan together, your dates, your island, your travel style, and make sure it actually works for your trip. Not someone else's version of Hawaii, but the trip for you. Alright, that's all I have for you today. Thanks so much for hanging out and being here. I hope that this has been helpful and maybe taking away some of the stress in your planning, or at least giving you a clearer sense of what to focus on and what to do next and where to go.

[00:12:23] Bryan Murphy: And until next time, as always. Live with Aloha

[00:12:31] 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. So. And music courtesy of our friends stick figure.