Ep. 193: 3 First-Time Hawaii Visitor Mistakes to Avoid

Planning your very first Hawaii vacation can be exciting and overwhelming all at the same time. Between flights, choosing which island, and figuring out where to stay, there’s a lot to think about.
But I’m going to share three simple first-time Hawaii visitor 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.
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I remember my first trip to Hawaii. It felt like a blur. There are things I wish I would’ve known, especially as I was planning and thinking about my trip. You probably already know where you want to stay, maybe you’re thinking about which island, but I’m going to cover three common mistakes that a lot of first-time visitors overlook.
Honestly, if you’ve been to Hawaii before, some of these tips might still be valuable because I didn’t quite pick up on or learn a lot of these things until after a few trips.
Travel Update for Hawaii Visitors
Before we get into the first-time Hawaii visitor mistakes, I need to update you on some travel news. If you’ve been following along, you know about the FAA and the flight cuts affecting travel, especially going into this holiday season. I’ve got some updated info specifically about travel to Hawaii.
The federal government shutdown began on October 1st and is still going on. As of November 11th (Happy Veterans Day, by the way—extreme gratitude to everyone who has served), we’re on day 42 of the shutdown. It’s the longest shutdown in US history.
What does that mean for Hawaii travelers? TSA agents and air traffic controllers are still working, but they’ve been doing so without pay. They just missed their second paycheck. The FAA ordered flight cuts last week to ease demand on control towers, which are short-staffed. Since then, airlines have canceled more than 9,000 flights across the US.
The good news for Hawaii travelers specifically? The islands have experienced some disruptions, but not major ones like the mainland. Hawaiian Airlines canceled just six inter-island flights on November 7th and 8th. Overall, things are running pretty smoothly. The major disruptions are hitting hubs like Denver, Atlanta, Chicago, Dallas, and the New York area.
If you’re traveling to Hawaii in the near future, here’s what I recommend:
- Check your flight status frequently—get the apps, notifications, emails, all the things
- Arrive at the airport earlier than you normally would (we’re planning three hours before our flight)
- Allow extra time for security and have a backup plan just in case
- Bring extra aloha for everyone involved, from TSA agents to flight attendants
Hawaii officials have been proactive. They’ve requested waivers and even offered to fund federal workers. State officials say airports are running smoothly right now and safety standards are being maintained. National parks have limited service, but most are still open.
The Most Common First-Time Hawaii Visitor Mistakes
After years of traveling to Hawaii and talking with thousands of first-time visitors through this podcast, I’ve noticed patterns. These first-time Hawaii visitor mistakes are easy to avoid once you know what to look for. Let me break down the top three.
Mistake #1: Trying to Do Too Much
This is by far the most common mistake I see and the one I’ve experienced personally. I totally get why it happens. You’ve been dreaming about visiting Hawaii maybe since forever. You’ve seen all the incredible photos—maybe you follow us on Instagram at @hawaiisbest—and you’ve got this list of things you want to do, see, and experience.
But the problem is people try to cram too much into their itinerary. They end up spending more time and money stressed out and traveling than actually enjoying and slowing down to experience Hawaii island time, the island pace, the vibes.
Here’s my advice: For your first trip, pick one island. At most, two if you’re staying 10 days or more. You can probably do two islands comfortably if you give yourself enough time.
Give yourself time to slow down. It’s going to take a couple days after traveling to really get the speed and pace of the islands. You want to explore without rushing. You want to stumble upon a little cafe, a hidden beach, someone selling local fruit on the side of the road. Those things require time. Build in some downtime. Maybe sleep in one morning. Spend an afternoon doing absolutely nothing but sitting at the beach.
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 I’ve found in slowing down and not getting bogged down by a packed itinerary is getting time to talk to the locals, getting time to talk to Hawaiians, and being able to hear their story. Hear why Hawaii is special to them. Understand that it’s not like just traveling between states—it’s a whole other world, a whole other culture. Slowing down really helps with that.
Mistake #2: Neglecting Hawaiian Culture
This is a big one because it’s about missing out on a richer experience, but it’s also about respect. Many first-time Hawaii visitor mistakes stem from not understanding that Hawaii isn’t just another beach destination.
It’s not like just going to a pretty beach. Hawaii has a 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. What’s special about that is we’re all guests in their home.
A lot of visitors treat Hawaii like it’s a tropical Playground, like it’s Disneyland or something with that type of mentality, without taking the time to learn about or respect the culture. That’s honestly a mistake. You’re missing out on some of the most meaningful parts of your trip.
What does it mean to engage with Hawaiian culture? Let me give you some practical ways to do that.
First, before you go, do a little research. Learn about Hawaiian history. We’ve got some incredible podcast episodes with culture practitioners. Understand what aloha really means. I did a whole deep dive with Kahooilina Sorio, who is a Hawaiian language teacher at Kamehameha Schools. He went over the word aloha for about 30 minutes. Once you understand that, it changes how you experience the islands. It really does.
Second, visit cultural sites with respect. For example, Iolani Palace. This year we’re going to 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 taking them to Iolani Palace and Bishop Museum this time around.
Third, support local businesses and artisans along the way. Seek out locally owned restaurants, shops, and tour operators when you can. Buy authentic Hawaiian crafts and products. There are farmer’s markets across all the islands. This helps the local economy and gives you a chance to connect with the people who call Hawaii home. Those connections—you’ll be surprised—are the ones you remember. Those are the ones that last a lifetime.
If you have a chance, attend a luau or cultural demonstration. Not the super touristy one, but ones that are actually focused on education and preserving Hawaiian traditions. Polynesian Cultural Center does a great job at this. Learn about hula, about traditional navigation, about Hawaiian values. These experiences will stay with you long after your trip.
Mistake #3: Worrying Too Much About the Weather
I see this all the time. Some of my highest-ranked blog posts are about weather during different times of year in Hawaii. People get caught up trying to figure out the absolute perfect time to visit. They’re researching the best month, the best times of the month, stressing out over weather forecasts, winds, hurricane season. A lot of people worry about rain or clouds ruining their trip.
This is one of those first-time Hawaii visitor mistakes that causes unnecessary stress. I totally understand, especially if you have family pictures planned or you want to go to a specific beach. I get it.
But the truth about Hawaii? It’s a tropical climate year-round. That means it’s pretty much always a good time to visit. Yes, some months might get a bit more rain. Some months might be a little windier depending on which side of the island you’re on—windward side or leeward side, dry or wet. There are subtle differences in the seasons, but we’re not talking about the difference between summer and winter in New York. We’re talking about 80 degrees versus 85 or 90 degrees. Whether you might get a brief rain shower in the afternoon or not.
My advice? Pick the time that works for your schedule and your budget. That’s what’s going to matter most. There are times during the year when it’s a little bit cheaper than peak season. You’re going to get a better deal if you travel mid-October versus July, for example. We love October. We love February. Those are our two favorite months.
Are there certain times of year that might be better for a specific activity? Absolutely.
If you want to see whales and that’s top of your list, visit between December and April. Even as early as October or November you might start seeing some whales, but official whale season is around December 15th. If you’re on Maui, you’re going to get the best opportunity to see migrating whales.
Winter months also bring big surf to the North Shore of Oahu. It’s an incredible time to watch professional surfers. (Don’t get in the water on the North Shore during wintertime on any North Shore-facing beaches.)
Summer months are drier. They’re great for snorkeling and calmer ocean activities. The North Shore—Waimea Bay, for example—is totally crazy how much it changes between summer and winter. It’s so much calmer during the summer months.
Every season in Hawaii has its own advantages. You really can’t go wrong. Don’t let weather worries dictate your entire trip and stress you out.
Pack some layers because evenings can be cooler, especially at higher elevations. Bring a light rain jacket just in case. Once you’re there, embrace whatever weather you get. Rain in Hawaii is better than rain anywhere else in the world, in my opinion.
How to Avoid First-Time Hawaii Visitor Mistakes
There you go. Those are the three biggest first-time Hawaii visitor mistakes I’ve seen people make—and I know I’ve made a few of these—on their first trip to Hawaii:
- Trying to do too much and over-scheduling your trip
- Neglecting Hawaiian culture and missing out on the deeper meaning of the islands
- Worrying too much about the weather instead of just embracing the experience
If you can avoid these three common mistakes that first-time visitors make, you’re going to have a better trip. You’ll come home more relaxed, 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, or incredible mai tais at Monkeypod (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.
If you found this helpful, drop me a review and rating. It helps other people find this podcast as they’re planning their trip to Hawaii.
Until next time, my friend, as always, live with aloha.
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- Best Time to Visit Hawaii for Families
- The True Meaning of Aloha w/ Kahanui Solatorio
- Hawaiian Words to Know Before Visiting
💻 Related blog posts:
- 23 Critical Things to Know for Planning a Trip to Hawaii
- 5 Ways to Travel Responsibly to Hawaii
- Best Time to Visit Hawaii
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Transcript
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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Bryan Murphy, owner of Hawaii’s Best Travel, is a certified Hawaii destination expert from the Hawaii Visitors Bureau. He actively participates in the Hawaii Visitors and Convention Bureau as a member and has a strong educational background focused on local culture and sustainability. As the host of "Hawaii’s Best Travel," a top-30 US travel podcast, Bryan combines his years of experience with valuable insights. He connects with a broad online community, reaching nearly half a million people, and offers a richer, more responsible way to experience Hawaii.









