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

3 First-Time Hawaii Visitor Mistakes to Avoid

• Bryan Murphy — Certified Hawaii Travel Expert & Owner of Hawaii’s Best Travel | Hawaii Travel Podcast • Episode 193

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What are the three planning mistakes most first-time Hawaii visitors don't see coming?

Planning your first Hawaii trip means navigating flights, islands, and accommodations—but the real pitfalls aren't what you'd expect.

👉 Hit play now to discover three under-the-radar mistakes that could derail your trip and learn how to avoid them for a smoother, more authentic Hawaii experience.

If you've ever wondered how to plan a Hawaii vacation that feels relaxed instead of rushed, this episode is for you.

You'll learn the most common planning traps first-timers fall into and exactly how to sidestep them before you book.

In this episode of Hawaii's Best Travel, Bryan unpacks three overlooked mistakes first-time visitors make so you can enjoy a more meaningful, stress-free Hawaii vacation.

👉 In this episode, you will:

  • Skip the over-scheduling trap and learn how slowing down creates space for authentic island moments
  • Connect with Hawaiian culture respectfully by supporting local businesses and visiting meaningful cultural sites
  • Let go of weather anxiety and pick travel dates that work for your schedule and budget

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Scroll up ⬆️ and hit play now to skip the common first-timer mistakes and plan a trip that captures the true spirit of Hawaii.

🎧Related episodes:

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💻Related blog posts:

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🤓Chapters:

  • 1:12 Travel News Update: FAA Flight Cuts and Shutdown Impact
  • 5:47 Mistake #1
  • 7:49 Mistake #2
  • 10:26 Mistake #3
  • 13:24 Final Thoughts and Tips

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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)

193_3 First-Time Hawaii Visitor Mistakes to Avoid


[00:00:00] Bryan Murphy: Planning your very first Hawaii vacation can be exciting and overwhelming all at the same time. You know, between flights, which island to choose where to stay. In this episode, you'll discover three simple mistakes, probably not even on your radar that could negatively affect your trip, and how to skip them for a smoother, more authentic Hawaii experience.

[00:00:26] Bryan Murphy: Aloha, and welcome to Hawaii's Best, the podcast, hoping you plan an unforgettable trip to Hawaii. I'm your host Brian Murphy, and I'm so glad that you're joining me today. And if you're planning your first trip to Hawaii, you're probably so excited. I remember. My first trip, it felt like it was a blur, but I'm gonna go over some of the things that I wish I would've known.

[00:00:46] Bryan Murphy: And this episode, especially for you as you're planning and thinking about your trip, you probably already know where you wanna stay. Maybe you're thinking about the island, but I'm gonna go over three common mistakes that a lot of first time visitors overlook. And honestly, if you've been to Hawaii before, some of these tips, I think you'll find valuable because a lot of these tips I didn't quite pick up on or learn after a few times of going to Hawaii.

[00:01:12] Bryan Murphy: But before we dive in, I feel like there's some travel news I need to update on if, if you listen to my last episode, talked about the FAA and the flight cuts and how that is gonna affect travel, especially going into this holiday season. Now, it's been a few days removed from that and have some updated info I wanted to bring to you about specifically travel to Hawaii.

[00:01:33] Bryan Murphy: And I think some of this can be applied to, because if you're listening to this, maybe you're not traveling to Hawaii this Thanksgiving or this holiday season, but maybe you are traveling somewhere else on the continent. So as you probably are aware, the federal government shut down. It began on October 1st.

[00:01:49] Bryan Murphy: It's still going on. Um, looking at the news yesterday on Monday, it looked like that there might be an agreement. I don't follow a lot of politics, but I do try to follow some of the headlines as, especially with this topic, um, it looks like there might be some agreement between the, uh, parties, but as of today, November 11th and Happy Veterans Day, especially honestly, too, if, if you served our country.

[00:02:15] Bryan Murphy: Someone in your family. Um, extreme gratitude. Uh, thank you for your service. I know thinking about my grandpa, thinking about my father-in-law who, uh, both served and some other family members as well, so brother-in-law. So appreciate everyone who has served. So. We're on day 42 of the shutdown. It's the longest shutdown in US History.

[00:02:37] Bryan Murphy: And what does that mean for Hawaii travelers? Well, TSA agents and air traffic controllers, which are super important for traveling safely. They're still working, but they've been doing so without pay and they actually just missed their second paycheck. But here's where things get even a little bit more complicated.

[00:02:55] Bryan Murphy: The FAA ordered flight cuts last week. You can go ahead and listen to, uh, my Friday episode, and this was in response to ease demand on control towers, which are short staffed during the shutdown. And from what I've learned, they're actually short staffed prior to the shutdown. Since then, airlines have canceled more than 9,000 flights across the us.

[00:03:15] Bryan Murphy: And another 1200 domestic flights were canceled Just yesterday, on Monday the 10th, the FAA increased its target for cutting flights at the nation's busiest airports to 6% up from 4%, and that set to rise to 10% by this coming Friday. Even though the government is set to reopen soon, hopefully these flight cuts aren't just gonna disappear overnight.

[00:03:38] Bryan Murphy: Transportation Secretary Sean Duffy said that the cuts will remain even after the shutdown ends, until safety metrics improve and staffing levels stabilize at air traffic control facilities. So unfortunately there's no timeline yet on when things will be back to normal. But a little good news is for Hawaii travelers specifically, the islands have experienced some disruptions, not major disruptions, like across the country compared to mainland.

[00:04:07] Bryan Murphy: For example, Hawaiian Airlines did cancel a handful. Inner island flights, just six flights on November 7th and eighth. But overall things are running pretty smoothly. I think I saw that there was a flight from Hawaii to, that might have been cut. The major disruptions are hitting hubs like Denver, Atlanta, Chicago, Dallas.

[00:04:26] Bryan Murphy: And the New York area are being hit the hardest right now. All that to say, if you're traveling to Hawaii in the near future, like my family is, here's what I would recommend. Check your flight status frequently, like crazy, frequent. Get the apps, get the notifications, get the emails, all, all the things.

[00:04:42] Bryan Murphy: Arrive at the airport earlier than you normally would. I know I stress ally out my wife. You know, flight leaves at seven. Yeah, we could, we could be there at six. So we're gonna plan on getting to the airport at three hours. That's our, that's our game plan. Even though we're going to a less crowded airport, long Beach, we're gonna plan to get there three hours before our flight.

[00:05:00] Bryan Murphy: So just allow extra time for security and honestly, have a backup plan just in case. Bottom line. Travel to Hawaii continues. Hawaii officials have also been proactive. They've requested waivers and even offered to fund federal workers, which is really cool. State officials say airports are running smoothly right now and safety standards are being maintained now.

[00:05:18] Bryan Murphy: National parks, that's another big question that I've gotten. National parks do have limited service, but most are still open. So if you're traveling Hawaii in the near future. Here's what I recommend. Bottom line, check your flight status. Frequently arrive at the airport earlier than you think you should, and just allow some extra time and extra grace.

[00:05:35] Bryan Murphy: So extra aloha for everyone involved from TSA agents to you know, flight attendants. All right? That's a longer update that I wanted to give you, but I think it's so prevalent, especially for those who are traveling this holiday season.

[00:05:47] Bryan Murphy: So let's get into the three mistakes. I'm gonna get right into mistake number one, and that's honestly probably the biggest mistake.

[00:05:55] Bryan Murphy: Something that we've learned over the years is trying to do too much. This is by far the most common mistake I see. Most common mistake I've experienced personally, and I totally get why it happens. You know, you're dreaming about visiting Hawaii maybe since like forever, and you've seen all the incredible photos.

[00:06:12] Bryan Murphy: Maybe you follow us on Instagram at Hawaii's best and you've got all the things in the list and you wanna do and you wanna see, you wanna experience, but the problem is. People try to cram too much into their itinerary and they end up spending more time, more money stressed out and traveling more than actually enjoying and slowing down and just experiencing Hawaii island time, the island pace, the vibes.

[00:06:37] Bryan Murphy: So with all that in mind, here's my advice for this mistake. For your first trip, you know, just pick one island or at most. Two, if you're staying maybe 10 days plus, you can probably do two islands comfortably. Give yourself some time to slow down. It's gonna take a couple days after traveling to really get the speed and the pace of the islands.

[00:06:58] Bryan Murphy: So you want to explore without rushing, you know, to stumble upon a little cafe, a hit of beach, someone selling some local fruit on the side of the road. Those things you want to build in time and just have some of that downtime, you know, maybe. Sleep in a morning, spend an afternoon doing absolutely nothing but sitting at the beach.

[00:07:17] Bryan Murphy: That's not wasting time. That's why you're in Hawaii. That's experiencing Hawaii the way it's meant to be experienced. One of the biggest things that I have found in slowing down and not getting so bogged down by a packed itinerary is. Getting time to talk to the locals, getting time to talk to Hawaiians, and just being able to hear their story and hear why Hawaii is special to them.

[00:07:41] Bryan Murphy: And just to understand, it's not like just traveling between states. It's a whole other world. It's a whole other culture and slowing down. Really helped with that.

[00:07:49] Bryan Murphy: Alright, let's go to mistake number two, and it kind of goes into what I was talking about and that is neglecting Hawaiian culture. This is a big one because it's about missing out on a richer experience, but it's also about respect.

[00:08:04] Bryan Murphy: So look, I mean, Hawaii isn't just another beach destination. It's, it's not like just going to a pretty beach. Hawaii has deep, rich, native Hawaiian culture that goes back over a thousand years. The Hawaiian people have their own language, their own customs, their own traditions, and their own history. And what's special about that is that we're all a guest in their home.

[00:08:26] Bryan Murphy: Unfortunately, a lot of visitors treat Hawaii like it's a tropical playground, like it's Disneyland or just something of that type of mentality. And without taking the time to learn about or respect the culture, and that's honestly a mistake you're missing out on some of the most meaningful parts of your trip.

[00:08:45] Bryan Murphy: So. What does it all mean to engage with Hawaiian culture? Well, let me give you some practical ways on how to do that. First, before you go do a little research, learn about Hawaiian history. We've got some incredible podcasts that we've done with some culture practitioners. I'll link those below, so that might be good, you know, after this episode, but understand what Loha really means.

[00:09:05] Bryan Murphy: I did a whole deep dive with Caho Nula Sorio, who is a Hawaiians language teacher at Kame schools, and he went over, it was like a 30 minute episode all about. The word aloha. Definitely recommend listening to that. And once you understand that it changes how you experience the islands, it, it really does.

[00:09:22] Bryan Murphy: And the second way is visit cultural sites with respect. So for example, going to Ani Palace, I know this year we're gonna be doing a lot more of that. I think our girls are a little bit older now and can appreciate some of the history. We're gonna be taking them to Iani Palace and Bishop Museum this time around.

[00:09:42] Bryan Murphy: And third, support local businesses and artisans along the way. So seek out locally owned restaurants, shops, tour operators when you can buy authentic Hawaiian crafts and products. There's a lot of farmer's markets across all the islands. This helps the local economy. And even gives you a chance to connect with the people who call Hawaii home, those connections, you'll be surprised.

[00:10:03] Bryan Murphy: Those are the ones you remember. Those are the ones that last a lifetime. If you have a chance, attend a luau or a cultural demonstration. Not the super touristy one, but the ones that're actually focused on education and preserving Hawaiian traditions. Um, PCC, Polynesia Culture Center does a great job at this, learn about hula, about traditional navigation, about Hawaiian values.

[00:10:22] Bryan Murphy: These experiences will stay with you long after your trip.

[00:10:26] Bryan Murphy: Now the third and final common mistake for first time visitors to Hawaii is worrying too much about the weather. I see this all the time and, and honestly, these are some of my highest ranked blog posts is about weather. During the different times of year in Hawaii, people get caught up so much in trying to figure out the absolute perfect time to visit Hawaii.

[00:10:46] Bryan Murphy: Researching the best month, the best times of month, stressing out over weather forecast winds, hurricane season. A lot of people worried about rain or clouds ruining their trip. I totally understand, especially if you have, maybe you have family pictures planned or you want to go to a beach. I totally get it, but.

[00:11:01] Bryan Murphy: The truth about Hawaii, it's a tropical climate year round, so that means pretty much it's always a good time to visit Hawaii. Yes, some months might get a bit more rain, some months might be a little bit more windy depending on the, the side of the island, if you're on windward side or leeward side, if it's dry or if it's wet.

[00:11:20] Bryan Murphy: And there are subtle differences in the seasons, but we're not talking about the difference between summer and winter. In New York, for example, talking about like 80 degrees versus. 85, 90 degrees. So whether you might get a brief rain shower in the afternoon or not, you might. But my advice would be pick the time that works for your schedule and your budget, and that's what's gonna matter most.

[00:11:42] Bryan Murphy: Because there are times during the year when it is a little bit cheaper than say, going peak, like around July, you're gonna get a better deal. Typically, if you travel like mid October. We love October. We love February. Those are our two favorite months, honestly. Now, are there certain times of years that might be better for a specific activity or thing to do?

[00:12:05] Bryan Murphy: Absolutely. So if you want to see some whales, and that's like top of your list visit between December and April E, even as early as. October, November, you might start seeing some whales, but official whale season is I think December 15th. And you'll start really, especially if you're on Maui, you're gonna get the best opportunity to see some of that, that migrating whales winter months.

[00:12:29] Bryan Murphy: Also bring some big surf to the North Shore, for example, of ahu. So it's a great, incredible time to watch some professional surfers don't get in the water in the North Shore during the wintertime. On any of the North shore facing beaches, summer months are drier. They're great for snorkeling. You got a little bit, a little bit more of calm ocean activities, especially the North Shore, if you're talking about North Shore Oahu, wame Bay versus summer and winter, it's.

[00:12:55] Bryan Murphy: Totally crazy how much it changes. It's so much calmer during the uh, summer months. But I mean, listen, every season in Hawaii has its own advantages. You really can't go wrong. Don't let the weather worries dictate your entire trip and stress you out. Pack some layers because evenings can be cooler, especially at higher elevations.

[00:13:14] Bryan Murphy: Bring a light rain jacket just in case, and then once you're there, embrace whatever weather you get because rain in Hawaii is definitely better than rain anywhere else in the world, in my opinion, at least.

[00:13:24] Bryan Murphy: All right, so there you go. Those are the three biggest mistakes that I've seen that people make. I know I've made a few of these for their first trip to Hawaii.

[00:13:33] Bryan Murphy: Number one, trying to do too much over scheduling your trip. Number two, neglecting Hawaiian culture and missing out on the deeper meaning of the islands. And number three, worrying too much about the weather instead of just embracing the experience. So if you can avoid these three mistakes, you're gonna have, I think a better trip.

[00:13:50] Bryan Murphy: You'll come home more, relax inspired with a genuine appreciation of what makes Hawaii so special, because at the end of the day, Hawaii. Isn't just about beautiful beaches, perfect sunsets, incredible maize at Monkey Pod. Shout out. It's about the spirit of the place, the warmth of the people, and the way it makes you feel when you slow down enough to really take it all in and experience the aloha of Hawaii.

[00:14:17] Bryan Murphy: Thank you for taking the time to listen to this episode today, and if you found it helpful, drop me a review, drop a rating and review if this episode has been helpful in your planning for your trip to Hawaii. And until next time, my friend as always, live with Aloha

[00:14:35] Bryan Murphy: Maah 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.


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