Hawaii Travel Mistakes to Avoid Before You Book
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You found a cheap flight. You asked ChatGPT to build your itinerary. You figured four islands in 10 days was totally doable. And now you’re wondering why your Hawaii trip felt rushed, expensive, and exhausting.
These are some of the most common hawaii travel mistakes visitors make, and they’re easy to avoid once you know what to look for.
In Episode 233 & 235 of Hawaii’s Best, I sat down with Jordan and Erica from the Hawaii Vacation Guide, one of the most trusted Hawaii travel planning resources online.
They’ve lived on both Oahu and Maui, they travel back regularly with their family, and they’ve made plenty of these mistakes themselves. So have I.
We covered 15 mistakes across five areas: planning, budget, safety, cultural respect, and experiences.
The first half covered planning, budget, and safety. Everything below picks up where that left off.
Podcast Episode Part 1
Podcast Episode Part 2
Don’t Trust AI to Plan Your Hawaii Trip
This is one of the biggest Hawaii trip planning mistakes right now, and it’s more common than you’d think.
Jordan and Erica get emails from listeners who built their entire Hawaii itinerary using ChatGPT or another AI tool.
The problem? Those itineraries are full of errors.
Places that no longer exist. Activities that aren’t appropriate to visit. Logistics that just don’t work on the ground.
One example Jordan shared: AI telling visitors they can walk to the lei stands from the Honolulu airport. You can’t.
The airport layout keeps changing, it’s not safe to walk with luggage, and the stands are easy to miss even when you’re driving.
It sounds like a small thing, but it’s a sign of a bigger issue.
AI doesn’t know what the signs say at Red Sand Beach on Maui.
It doesn’t know which trails have been closed or rerouted. It doesn’t know what’s changed in the last six months. It pulls from what’s popular online, not what’s actually safe or current.
Popular on the internet doesn’t mean you should go there.
Erica’s take: use AI as a brainstorming tool, not a final answer.
If you use it, cool. But verify everything against sources written by people who’ve actually been there recently. That’s the move.
AI even warns you itself that it makes mistakes. Take that warning seriously.
Island Hopping and Overpacked Days Are Costing You the Real Trip
Here’s something a lot of families do: try to see everything.
The only guest post Jordan and Erica have ever published on their site was from a guy who did all four islands in 14 days with his wife.
His honest review? Exhausting.
Every three days they were packing up, returning a rental car, flying to the next island, and starting over. They saw a lot. They experienced very little.
Jordan and Erica’s recommendation for a 10 to 14 day trip: pick one or two islands and go deeper. You’ll actually get the feel of a place. You’ll stop at the food stand. You’ll talk to someone who lives there. You’ll understand the pace of the island.
That’s the stuff you remember.
If you’re still figuring out which island fits your trip, this guide on choosing the best island in Hawaii can help you narrow it down.
And if you’re thinking about island hopping, read up on what traveling between islands in Hawaii actually involves before you commit.
A 30-minute inter-island flight sounds easy until you factor in checking out of your hotel, returning your rental car, TSA, checking in on the other side, and picking up a new car.
That’s your whole day. If you’re traveling with kids, it’s even more of a haul.
The same logic applies to daily itineraries. Jordan used to pack every day full. Erica and the kids pushed back.
Now their rhythm is: go out early, see something great, then chill for the rest of the afternoon. The trade winds pick up anyway, and mornings in Hawaii are the best part of the day.
Go out, do the thing, then come back and breathe.
Jordan also mentioned their New Year’s trip to Lahaina on Maui.
They expected a fun night out. They walked home at 10:30 PM because the island had already shut down.
Hawaii goes to bed early. Plan for it, especially if you’re visiting smaller towns or heading to Kauai where things close up fast.
This is especially true for traveling with kids to Hawaii.
Budget Traps: Mistakes to Avoid in Hawaii Before You Book Anything
Let’s talk about the mistakes that hit your wallet hardest, because there are a few that catch people completely off guard.
Book lodging before you book your flight.
You see a flash sale from Southwest or United and you book it immediately. Then you look at hotels and realize the math doesn’t work.
Jordan and Erica call this the biggest planning pitfall.
Start with lodging. Know what it costs of a Hawaii trip. Then find your flight around it. A cheap flight means nothing if you can’t afford a decent place to stay.
Lodging is about 50% of your total trip cost.
Jordan and Erica have run the numbers across budget, mid-range, and luxury trips.
It’s consistently around half.
That’s before you add Hawaii’s transient accommodations tax, which runs around 18.5% depending on the island. It’s not hidden in the fine print anymore thanks to new federal rules, but it still catches people off guard when they see the final bill.
What looked like a reasonable nightly rate ends up being a lot more by checkout.
Parking adds another $40 to $60 per night at most hotels. And if you’re renting a car, that cost stacks on top of everything else.
For rental cars, Jordan and Erica recommend Discount Hawaii Car Rental for the rates and the no-prepayment flexibility. You can cancel and rebook if rates drop, which they often do.
They also mentioned local options like KeHE Rent a Car on Maui and Joe’s Jeeps on the Big Island if you want to keep your money in the community.
If you’re staying in Waikiki and not planning to leave much, you might not need a car at all. Oahu has the best public transit of any island, and Uber works well there too.
Drive times are not what the map says.
This one catches people on every island. The Road to Hana is 52 miles from Kahului. It takes most of the day.
Narrow roads, one-lane bridges, local traffic, and stops along the way make it a full commitment.
If you’re planning that drive, read this first: Rethinking the Road to Hana on Maui.
Kona to Hawaii Volcanoes National Park is 1.5 to 2 hours each way.
Erica used to commute from Ko Olina to downtown Honolulu and had to leave at 5:05 AM just to beat traffic. She was still in traffic.
Factor drive time into every day you plan, and check for road construction before you go. It’s been bad on several islands lately.
Ocean and Trail Safety: The Mistakes That Matter Most
This is where the stakes get real.
Drowning is the number one cause of death for visitors to Hawaii.
That’s not meant to scare you. It’s meant to make you take the ocean seriously, because a lot of people don’t until it’s too late.
An empty beach is not a hidden gem. It’s usually a warning sign.
If locals aren’t swimming there, there’s a reason.
The ocean in Hawaii is not like the ocean in Southern California or Florida.
The reefs, the drop-offs, the currents, and the shore break are all different. Even experienced swimmers get caught off guard.
Bryan’s advice: swim at lifeguarded beaches and go talk to the lifeguard before you get in the water
Ask about flags, currents, and conditions.
As Erica put it, they’d rather talk to you than rescue you later.
Jordan met a lifeguard in Maui who surfaced from clearing fishing lines and bumped into an 8-foot tiger shark.
Another lifeguard on Oahu had to take a lunch break from his shift to go win the Eddie Aikau big wave competition.
These people know the ocean better than anyone. Use that resource.
If you’re not a strong swimmer and you want to snorkel, book a guided tour.
Either a boat-based snorkel tour or a shore-based tour with a guide in the water with you. You’ll still see everything you came to see.
The turtles, the fish, the reef. And someone will be there with you if something goes wrong.
Erica said it clearly: there are so many safe ways to have this experience. Don’t skip it just because you’re not a confident swimmer, but don’t go out alone either.
For hiking, start early.
I pushed a stroller up the Makapuu Lighthouse Trail at 9:30 AM with little kids and it was brutal. Hot, exposed, and relentless.
Jordan and Erica made the same mistake at Koko Head Crater with a three-year-old. Diamond Head, Makapuu, and any sunrise hike need an early start, before 7 AM if you can manage it.
If you’re looking for trails that work well for families, this list of kid-friendly hikes on Oahu is a good starting point.
One more thing on safety: your weather app is probably giving you the wrong picture.
Searching “Maui weather” shows you conditions across multiple ecosystems on the island. It might show rain somewhere and make you think your whole day is ruined.
Search the exact area where you’re staying, like Kaanapali or Wailea, and check that specifically.
The leeward side of any island, places like Ko Olina on Oahu, tends to be drier and sunnier than the windward side. Waikiki technically doesn’t even get enough rain to qualify as a tropical climate.
Rain in Hawaii is usually short and followed by a rainbow anyway.
What to Do Before You Go
These come straight from the conversation with Jordan and Erica:
- Book lodging first, then find your flight around it
- Stick to one or two islands for trips under two weeks
- Search your exact location for weather, not the whole island
- Start hikes before 7 AM on hot, exposed trails
- Book a guided snorkel tour if you’re not a confident swimmer
- Talk to the lifeguard before you get in the water at any beach
- Recheck rental car rates closer to your trip, deals shift often and you can usually rYes, the second draft was a bit shorter than the first. Here’s the full article at the same length as the original, with all the internal links woven in.
Trespassing, Closed Areas, and What Not to Do in Hawaii
This is where hawaii travel mistakes start to carry real consequences.
Trespassing to reach popular spots is one of the most common things visitors do without realizing it’s a problem.
Some of it is unintentional. A lot of it isn’t.
Red Sand Beach on Maui is a good example.
It consistently shows up on travel itineraries and “must-see” lists. The path to get there crosses private property.
The beach is also considered a sacred site. There are signs. People walk past them anyway.
Stairway to Heaven on Oahu is another one. There has been ongoing legislation around managed access, but as of this recording it is closed and off-limits.
Some visitors look for a back route. The problem is that once you step onto the platform, you’ve crossed private property regardless of how you got there.
Queen’s Bath on Kauai has a death count posted at the trailhead. That’s not decoration. It’s information.
Erica made a point worth repeating here: the visitors most likely to end up in these situations aren’t reckless people.
They’re usually well-meaning travelers who see 30 other people walking past a sign and figure it must be fine.
It’s not.
The crowd does not make it legal or safe.
If you see kapu signs, keep out signs, or no trespassing markers, respect them. That’s what not to do in Hawaii regardless of what you saw on someone’s Instagram grid.
Don’t Skip Hawaiian Culture
Skipping the cultural side of Hawaii is one of the quieter Hawaii travel mistakes, but it costs you more than you’d think.
Hawaii was a kingdom. It has a living language, a complex history, and a culture that’s still very much present.
Visitors who take even a little time to engage with that come home with a completely different experience.
Jordan and Erica offer a few easy entry points. A guided tour with a local is one of the best. Guides share real stories, local pidgin, hidden spots, and context you’re never going to get from a search engine.
An outrigger canoe ride counts. So does the Bishop Museum, which is far more interactive than most people expect.
The luau conversation is worth a note. A lot of travelers dismiss luaus as tourist traps.
Jordan and Erica have been to most of them as part of their research, and their honest take is that the performers are exceptional across the board.
The dancers and fire knife performers train seriously. The authentic elements hold up.
Where luaus vary is in the setting, the food, and the overall atmosphere.
If you’re comparing them, think about what matters most to you: oceanfront sunset views, a hilltop setting, the food quality, or the overall production value.
Every luau has something worth experiencing. None of them are a waste.
Understanding what not to do in Hawaii culturally comes down to this: show up with curiosity and respect.
You don’t need to have a degree in Hawaiian history. You just need to be willing to listen.
Your Trip Will Not Be Perfect
This one applies to any destination, but Hawaii brings its own version of it.
Trips to Hawaii are expensive, they’re emotional, and for a lot of families, they’ve been planned for months or years.
That investment can turn into unrealistic expectations about how everything will go.
Weather will not always cooperate. Restaurants fill up. Tours get canceled for safety reasons. Waves show up during snorkel season. You might get sick.
Jordan and Erica shared a trip where their whole family came down with a virus. That happened in Hawaii.
Bryan had a kidney stone during one of his trips. These things happen and they do not ruin the trip unless you let them.
The mindset shift is simple: don’t lock onto one version of how the trip is supposed to go.
Hawaii offers enough that when one thing falls through, something else opens up.
That’s good general travel advice. It’s especially true in a place like Hawaii where the weather changes fast, the pace is different, and the best moments often aren’t the planned ones.
Reservations Matter More Than Ever
Not getting reservations is one of those Hawaii travel mistakes that’s growing every year. The list of places requiring advance booking keeps getting longer, and some of the reservation windows are easy to miss.
Diamond Head and Hanauma Bay have required reservations for a while.
More recent additions include Waimea Valley on Oahu and Iao Valley State Park on Maui. Haleakala sunrise requires reservations. Sunset at Haleakala does not.
The rules vary by experience and change over time, so double-check anything you’re planning closer to your trip.
The booking windows also vary. Some spots open reservations 60 days out. Others are 72 hours. Luaus and boat tours should be booked as soon as you know you want them.
Mama’s Fish House on Maui is probably the most talked-about example in this conversation.
It’s widely considered one of the best restaurants in Hawaii.
Reservations typically open six months out and fill quickly. If you show up without one, your best move is to stop in the day before and ask about any openings for the following day.
Lunch is sometimes more available than dinner, though that window has closed up too.
The restaurant is oceanfront and worth making the effort for.
This is what not to do in Hawaii if you want to eat at the places people rave about: assume you can walk in. You probably can’t.
Plan the Right Trip for You, Not Someone Else’s
The last Hawaii travel mistake on this list is trying to recreate someone else’s Hawaii vacation.
Social media has made this worse. Visitors show up trying to hit every iconic photo spot, chase the most impressive itinerary, and document proof that they did Hawaii right.
That approach tends to make for a stressful, expensive, and often shallow trip.
Here’s what it’s actually okay to do:
It’s okay to skip the Road to Hana.
It’s okay to skip island hopping entirely.
It’s okay to not snorkel.
It’s okay to not hike.
It’s okay to spend your afternoon by the pool.
It’s okay to stay on one island for your whole trip.
It’s okay to skip Instagram altogether.
The best Hawaii itinerary is not the busiest one or the most impressive-looking one. It’s the one your family actually enjoys.
Jordan and Erica’s travel rhythm: up early, coffee, out the door to experience something, then back at the hotel by mid-afternoon for beach time and wind-down.
One activity per day, done well, beats five rushed stops every time.
Some of Bryan’s most vivid Hawaii memories aren’t the planned experiences.
They’re a stranger handing his then four-year-old daughter a ukulele on the shuttle bus from the airport, and her face in that moment.
That wasn’t on any itinerary.
The real Hawaii travel mistakes are the ones that keep you from being present for moments like that. Do less. Go slower. Let Hawaii happen.
What to Do Once You’re There
A few practical reminders for the on-the-ground part of the trip:
- Check reservations for every attraction, not just the obvious ones. The list keeps growing.
- Book popular restaurants early. Six months out for places like Mama’s Fish House is not an exaggeration.
- Respect closed areas and signage. Kapu means stay out.
- Do at least one cultural experience. A guided tour, a luau, the Bishop Museum. Something.
- Pack light. Hawaii is the one destination where three checked bags is always the wrong call.
- Let your days breathe. One thing done well beats five things done exhausted.
- Ignore Instagram while you’re there. The trip that looks less impressive online is often the one you’ll actually remember.
Listen to the Full Conversation
Parts one and two of this conversation cover all 15 of the most common hawaii travel mistakes Jordan, Erica, and Bryan see visitors make.
If you haven’t listened to both episodes, both are linked below.
Jordan and Erica’s full library of guides, videos, and planning resources lives at The Hawaii Vacation Guide.
Their YouTube channel under the same name is one of the best visual resources for Hawaii trip planning available.
Our Favorite Hawaii Travel Resources!
🏨 Accommodations: We recommend Booking.com
✈️ Flights: For the cheapest flights, we use Skyscanner
🚗 Rental Car: We recommend Discount Hawaii Car Rental
🌋 Attractions: We recommend Viator
🌺 Luaus and Tours: We recommend Hawaii Tours
📱 Mobile Tour App: Our favorite is Shaka Guide
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Transcript
233_Hawaii Travel Mistakes We See Visitors Make Again and Again with The Hawaii Vacation Guide
[00:00:00] Common Planning Traps
[00:00:00] Bryan Murphy: It’s tempting and easy to book the cheap flight before checking hotel rates. It’s easy to trust AI with your itinerary. It’s easy to think four islands in 10 days. Sounds doable, and it’s easy to underestimate the ocean, the weather drive times, and the reservation rules. The goal for this episode is not to make you feel bad or scold you for making these mistakes.
[00:00:20] Bryan Murphy: The goal is to help you plan a better and more fulfilling trip. To Hawaii
[00:00:30] Meet the Hosts
[00:00:30] Bryan Murphy: loha and welcome to Hawaii’s Best. I’m Brian Murphy, Hawaii, destination expert and your personal guide to planning an unforgettable trip to Hawaii. Today I’m joined with Jordan and Erica from the Hawaii Vacation Guide, and we’re talking about 15 Hawaii travel mistakes that we see visitors make again and again in some of these.
[00:00:50] Bryan Murphy: I’ve made, and I know Jordan and Erica have made, and we’ll talk about that throughout this episode. But some of these are, you know, they cost you money. Some of these mistakes, cost time, some affect safety and some shape the way that you visit or show up in Hawaii. So by the end of this episode, you’ll know what to skip, what to plan for ahead of time, and how to make your trip feel a lot less stressful.
[00:01:14] Bryan Murphy: Jordan and Erica are the creators behind the popular, the Hawaii Vacation Guide, and it’s one of the most trusted Hawaii travel planning resources online. They’ve both lived on Oahu in Maui and now travel back as often as they can with their family as they continue creating practical Hawaii travel guides, videos, and itineraries.
[00:01:33] Bryan Murphy: Their YouTube channel under the same name. The Hawaii Vacation Guide, uh, focuses on firsthand Hawaii travel tips, honest recommendations, and practical planning help for visitors.
[00:01:43] Why These Mistakes Matter
[00:01:43] Bryan Murphy: And one of the reasons I’m excited for this conversation today is because I feel genuinely aligned with the way they share and talk about Hawaii.
[00:01:52] Bryan Murphy: They don’t treat the islands like a theme park. Backdrop or a checklist, or just another pretty backdrop for vacation content. They understand that Hawaii is a real place. It’s home to real people with a living culture, deep history, local communities, and places that deserve care and respect. That matters so much more today because there’s a lot of Hawaii content online right now.
[00:02:15] Bryan Murphy: Some of it is helpful, some of it is just built to get affiliate clicks or to sell something or to make Hawaii look like a fantasy version of itself. But planning a good Hawaii trip takes more than just chasing the prettiest. Beaches or the trendiest restaurants. It means knowing what’s worth your time, what needs to be booked ahead of time, what places require extra care and how to visit in a way that supports the people and places that make Hawaii so special.
[00:02:42] Bryan Murphy: So let’s go ahead and let’s talk story with Jordan and Erica from the Hawaii Vacation Guide.
[00:02:53] Bryan Murphy: Jordan and Erica, welcome to Hawaii’s Best. Thank you so much for coming on today, guys. Great. Yeah, thanks for having us, Brian. Good to be teaming up on this. Yeah, I’m excited about this.
[00:03:03] Planning Bucket Overview
[00:03:03] Bryan Murphy: I think this is like one of those episodes where we could have made a list even longer. I think when I put our list together, Jordan, it ended up being like 40 or something.
[00:03:10] Bryan Murphy: Mistakes. Oh. And we kinda narrowed it down to 15 and we got, we’re gonna go over like. Five buckets. We’re gonna go through planning mistakes, budget mistakes, safety, cultural respect and experiences. And I think before we get into the list, you guys probably share the same feeling as like the goal is not to make anyone feel bad or about like, you know, getting something wrong.
[00:03:32] Bryan Murphy: I think most people just want to have a good trip and they want to do it respectfully. Especially if they’re listening to this podcast, they’re following with you guys. You guys do that so well, but they’re spending a lot of money. They’re excited. And for some people this is like a once in a lifetime vacation.
[00:03:47] Jordan – The Hawaii Vacation Guide: Yeah. We’ve, we’ve made these mistakes too. Like that’s why we share ’em. Exactly. Yeah. We’ve lots of examples and I mean, this just
[00:03:54] Bryan Murphy: happens. It just happens to people. Happens
[00:03:56] Jordan – The Hawaii Vacation Guide: everywhere. Yeah. Just, yeah,
[00:03:58] Bryan Murphy: exactly. I think along the way it’ll be, um, you know, I’ll definitely be sharing some of my mistakes and I think for the most part, people aren’t going with ill intent.
[00:04:08] Bryan Murphy: We’ll just kick it right off with. Bucket number one, talking about planning mistakes.
[00:04:13] AI Itinerary Pitfalls
[00:04:13] Bryan Murphy: Mistake number one. I really like this one, what you guys sent over using AI for your itinerary. Maybe you could just speak into that a little bit. Everyone’s using chatt, pt, Claude, all that. Yeah. We
[00:04:24] Jordan – The Hawaii Vacation Guide: even use AI for travel ideas and try to get like new ideas and see what’s there
[00:04:29] Erica – The Hawaii Vacation Guide: on our trip.
[00:04:30] Erica – The Hawaii Vacation Guide: We’re going on next week. We’re using ai.
[00:04:31] Jordan – The Hawaii Vacation Guide: What we’ve been finding is that, uh, people have been emailing us itineraries that come from ai, and you know what? They’re just, they’re just full of mistakes of like, just like wrong places or things that don’t exist anymore, or things that aren’t appropriate to go do.
[00:04:46] Jordan – The Hawaii Vacation Guide: Yeah. Or just kinda like, just not good advice. Like they could still have a good trip. They probably have some good stories to tell afterwards.
[00:04:51] Erica – The Hawaii Vacation Guide: Just double check. So if you use it. Cool. Awesome. But just double check everything because you know, they always give you that warning, like AI makes mistakes and it does.
[00:05:00] Erica – The Hawaii Vacation Guide: Yeah. So just don’t treat it as gold.
[00:05:02] Bryan Murphy: What are some of your guys’ flags like, oh, that this is definitely
[00:05:06] Jordan – The Hawaii Vacation Guide: created by ai. The simple one is like when you land in Honolulu and you can walk to the lay stands. They have these really QA stands by these like ladies out there. Right. They’re, they’re iconic, but you can’t walk to them.
[00:05:17] Erica – The Hawaii Vacation Guide: I mean, you could, that would be very hard. Hard. Yeah.
[00:05:20] Jordan – The Hawaii Vacation Guide: Honolulu airport’s hard to get around. Yeah. It’s not the safest to walk to them, and like, you just don’t, you drive over to them. That’s the little one. But I mean, also, you’re gonna be there with your bags and trying to get, and they’re easy to miss too.
[00:05:29] Jordan – The Hawaii Vacation Guide: You’re drive, they’re, they’re easy to. They are. Yeah. They, they keep rerouting Honolulu airport right now, you know, so that’s just like a little one. But still, like, I mean, he’d be with my bags trying to find like the lat stands, trying to walk
[00:05:39] Erica – The Hawaii Vacation Guide: to the lat stand that GPT told me I could walk to.
[00:05:42] Jordan – The Hawaii Vacation Guide: Yeah. Just, you know, and then other stuff too, and we’ll get into like things that are unsafe, like visiting the Red Sand Beach and things like that because it’s, it’s, there’s stuff that are popular.
[00:05:52] Jordan – The Hawaii Vacation Guide: On the internet, but that doesn’t mean you should go to them. And like there’s big signs there that says don’t do it, but that doesn’t come on the internet so that the computers don’t learn that way. We like to trust people who’ve been to Hawaii.
[00:06:01] Bryan Murphy: Right. Well, let’s keep going.
[00:06:02] Island Hopping Reality Check
[00:06:02] Bryan Murphy: So no mistake number two. Uh, this is one I actually, I think it was a episode or two ago, so if you’re listening, go back.
[00:06:08] Bryan Murphy: I’ll definitely link it below. But talking about. Island hopping and specifically, uh, Jordan, you mentioned this one visiting all four islands in like 14, 10 days. Yeah. We totally get, wait, what’s the wrong, what’s wrong with that? Yeah, no, there’s nothing. Right? There’s nothing.
[00:06:23] Erica – The Hawaii Vacation Guide: It’s the trip you want.
[00:06:24] Jordan – The Hawaii Vacation Guide: Yeah.
[00:06:24] Jordan – The Hawaii Vacation Guide: Like we had, the only guest post we’ve ever had on our website is this guy. He did, him and his wife did, he did all four islands in 14 days. And like, he rode up his adventure and he’s like, it was exhausting because like every, like. Essentially three days they were moving, they’re moving onto something else, either another hotel or another island, and it was, it was just a lot.
[00:06:42] Jordan – The Hawaii Vacation Guide: And usually what we find is people who are coming from Europe. They’re usually coming over for like three to four weeks. So they wanna go all the islands and they’re not coming back again. That’s great. Sure. But you know, if you’re coming from the mainland, uh, you know you’re gonna come back to Hawaii again if you really love it.
[00:06:55] Jordan – The Hawaii Vacation Guide: So just pick one, two islands if you’re staying for like 10 to 14 days and that’ll be enough island hopping, that’s what we recommend anyways. I think a lot of it comes down to maybe people like can’t decide which island to do, so they do ’em all.
[00:07:06] Erica – The Hawaii Vacation Guide: But then you miss some really amazing experiences on the island that you, you know, on each island.
[00:07:11] Jordan – The Hawaii Vacation Guide: So, yeah, try to stick to one or two. Yeah. And, and
[00:07:13] Erica – The Hawaii Vacation Guide: go deeper.
[00:07:14] Bryan Murphy: Yeah. And go deeper. That’s a good way to look at it. Mm-hmm. You get the vibe and the pace of the island when you slow down and stop at that food stand or talk to that person and taking the time to like just each island in each area, the island kind of has its own pace and its feel.
[00:07:30] Bryan Murphy: So getting the, you know, getting that. I mean, you’re not gonna like end your trip with a island hopping badge or anything like that. But it’s important to like consider, especially if you’re traveling with a family, right? Like if you’re traveling with a family, a 30 minute flight seems like super doable, but it’s basically your whole day, you know?
[00:07:47] Bryan Murphy: You still gotta do the airport, you still gotta do TSA. You still gotta check in, check out, return your
[00:07:51] Erica – The Hawaii Vacation Guide: car, get another one.
[00:07:53] Bryan Murphy: Exactly. Yeah. It’s a full domestic flight. A hundred percent.
[00:07:56] Stop Overpacking Days
[00:07:56] Bryan Murphy: So mistake number three. I think it kind of goes within, it is something that I’m kind of passionate about is building your itinerary.
[00:08:02] Bryan Murphy: We already talked about chat tutee, and this is something that it can give you a, like Disneyland style, this huge itinerary of things you’ve, you’ve must do. And honestly, I, you know, I totally understand why it happens, people. They’re spending a lot of money to get to Hawaii and they may not ever get back.
[00:08:17] Bryan Murphy: You know, they’re adding everything in and one beach day in Honolulu and then you want to get up to Sharks Cove and, and snorkel, and then you wanna get to Kailua for some lunch and then head over to the west side of Colina and check out the sunset. Like that itinerary is so crazy and you’re, to be tired, you’re need to be drained.
[00:08:34] Bryan Murphy: You know, Hawaii is not DSLand, and I don’t mean that in, in a negative way. Mm-hmm. But I think when we get into the cultural side of. Our conversation, it’s more than just the postcard diamond head view. Mm-hmm. It’s about slowing down. It’s about talking to people who actually live there or just understanding the history and doing some of that research prior to visiting the complex, yet beautiful history of
[00:08:58] Erica – The Hawaii Vacation Guide: Hawaii.
[00:08:59] Erica – The Hawaii Vacation Guide: Yeah. I definitely agree with you.
[00:09:01] Jordan – The Hawaii Vacation Guide: I like that. Just like overall, it’s just don’t overload your itinerary. Just leave those, the time in it for beaches or relaxing. Maybe go out in the morning, then go back to your hotel before the trade winds pick up.
[00:09:11] Erica – The Hawaii Vacation Guide: This is what we have learned. We, we’ve, yeah, Jordan likes to be Go, go, go.
[00:09:16] Erica – The Hawaii Vacation Guide: Yeah. I
[00:09:16] Jordan – The Hawaii Vacation Guide: love to load up these big itinerary days. You know, a lot of it. Filming and checking things out and like, we have our buckles. Oh, we, you haven’t been there in two years. We have to go check it out.
[00:09:23] Erica – The Hawaii Vacation Guide: The kids. And I really love some beach and pool time and what we’ve been doing is like, we’ll go out in the morning, we’ll go see something awesome.
[00:09:31] Erica – The Hawaii Vacation Guide: We’ll go experience something and then we are chilling out the rest of the day.
[00:09:35] Bryan Murphy: Yeah.
[00:09:35] Erica – The Hawaii Vacation Guide: And it’s been a great, great cadence for our
[00:09:37] Jordan – The Hawaii Vacation Guide: family. Have, I’ve learned. I’ve
[00:09:39] Bryan Murphy: learned, it’s funny, it sounds like my wife Allie, like she just wants to do the pool and, and. Hang out at the resort and do the things we usually do.
[00:09:47] Bryan Murphy: I’m like, well I got, you know, I’ve been talking to this guy. I want to, you know, I wanna go check out this new experience. Mm-hmm. And it’s like, I guess
[00:09:53] Erica – The Hawaii Vacation Guide: I do, I do like getting out in the early, now that we have like our new schedule,
[00:09:58] Jordan – The Hawaii Vacation Guide: I appreciate Yes. It nice way, way to start the islands wake up early, which I love about the islands, so it’s nice to get out there and it go sleep early too.
[00:10:03] Jordan – The Hawaii Vacation Guide: So it’s just nice to start your day early and then chill out at night.
[00:10:06] Bryan Murphy: Yeah. You know, that’s something a lot of people don’t realize, you know, especially on Kauai, the island starts closing down pretty, there’s not a huge nightlife scene, you know, so it starts shutting down. Like it kind of forces you back in your room and like, all right, well, and you wake up with the sun, which I love doing, so Yeah, I like that pace.
[00:10:24] Bryan Murphy: Mm-hmm.
[00:10:24] Jordan – The Hawaii Vacation Guide: We did, uh, we did Lana one time for New Year’s in our twenties. We’re like, yeah, we’ll go to Lana. Like, we’re not big party of yours, but, we’ll, new Year’s Lana Lana’s a fun bar town. Like, oh my God, it was so dead. It was, I mean, the people were out. We all, but like it was
[00:10:36] Erica – The Hawaii Vacation Guide: We walked.
[00:10:37] Jordan – The Hawaii Vacation Guide: Yeah, yeah. We
[00:10:38] Erica – The Hawaii Vacation Guide: walked home like during,
[00:10:40] Jordan – The Hawaii Vacation Guide: yeah.
[00:10:40] Jordan – The Hawaii Vacation Guide: Yeah. 10 o’clock, 10
[00:10:41] Bryan Murphy: 30. We’re like, alright, new Year’s is over here.
[00:10:43] Budget Bucket Begins
[00:10:43] Bryan Murphy: So probably one of the biggest is budgeting, especially right now, I didn’t mention it, but island hopping, inner island travel is getting more expensive. Obviously flights from the mainland are expensive.
[00:10:56] Flights Before Hotels
[00:10:56] Bryan Murphy: So bucket number two, budget mistakes and specifically mistake number four, finding a good airplane ticket without checking hotel rates.
[00:11:05] Jordan – The Hawaii Vacation Guide: Yeah, we call this like the biggest pitfall when you’re planning your trip. It’s like you get a flash sale from Southwest or United has this killer deal come from the East coast and you book it the flight to Hawaii and then you realize like, oh my gosh, the hotel is gonna cost me a fortune. This is not gonna be fun.
[00:11:23] Jordan – The Hawaii Vacation Guide: Mm-hmm. Because now like, and that’s what we found through research we’ll get into is, is that most of your trip costs is the logic. Even if you’re doing a budget trip or value trip. So you gotta be worried about those airline tickets. I mean, it’s great if you get a good deal, don’t get me wrong. Yeah. But don’t like be that reason to jump to Hawaii like next week.
[00:11:38] Jordan – The Hawaii Vacation Guide: We found understanding your full costs. Now you’re right. A lot of things have changed with airline tickets. Like they’ve gone up a lot in the last year, so maybe people aren’t getting those flash sales anymore, but you know, but just maybe. We’ll see what happens in the future.
[00:11:49] Bryan Murphy: Yeah. And with lodging, we’re you gonna touch on that next?
[00:11:53] Bryan Murphy: Especially with the new, I think it’s 17 or 18% total tax now that went into effect this past January. So that is a definitely a sticker shock, especially you see something advertised online is like, oh, that, that’s not actually the final bill.
[00:12:08] Lodging Is Half the Cost
[00:12:08] Bryan Murphy: So mistake number five. Would be 50% of your cost to lodging.
[00:12:13] Jordan – The Hawaii Vacation Guide: We, we like to do budgets and do articles and videos and like I about a trip to Hawaii cost.
[00:12:17] Jordan – The Hawaii Vacation Guide: We do it for ourselves too. And like what we found is like, you know, if, if you do a value trip to Hawaii mid-range or even a luxury trip, right? That lodging bucket. Is this always gonna be around 50% of, of your total trip, and that’s a lot, 50%. So it’s really knowing that, and it’s kinda like the nicest first thing to look at when you’re booking a trip to Wise, like, all right, where am I gonna stay?
[00:12:35] Jordan – The Hawaii Vacation Guide: Maybe I don’t care about lodging. Maybe I’m gonna be out exploring the islands all day. So I just wanna place it in my head, like in a, you know, a two star hotel or something. Or a vacation rental or maybe you on that luxury trip, but just know that the lodging’s gonna be a big part of that and, and then you’re right with fees.
[00:12:49] Jordan – The Hawaii Vacation Guide: It’s nice. There’s new federal laws, so across the US they can’t hide resort fees anymore. Those are already in the cost of your, of your room rate. But you’re right, it’s like an 18 and a half percent dependence on the island.
[00:13:00] Hidden Lodging Fees
[00:13:00] Jordan – The Hawaii Vacation Guide: You’re your transient accommodations. Tax.
[00:13:02] Erica – The Hawaii Vacation Guide: And then parking.
[00:13:03] Jordan – The Hawaii Vacation Guide: And then parking too, because that rental car, oh yeah.
[00:13:05] Jordan – The Hawaii Vacation Guide: Then that’s 40 to $60 a night plus that TAT tax. So I’ll all adds up. That lodging bucket can get really big.
[00:13:12] Best Rental Car Deals
[00:13:12] Jordan – The Hawaii Vacation Guide: What do you guys recommend for rental cars? Ooh, yeah, that’s a good one. So it, right. Our big thing is always recheck rates. Especially like this summer, like we’re gonna see what happens with visitor counts, but we love why discount car rental.
[00:13:25] Jordan – The Hawaii Vacation Guide: Discount.
[00:13:25] Erica – The Hawaii Vacation Guide: Hawaii Car Rental. Thank you.
[00:13:27] Jordan – The Hawaii Vacation Guide: Discount environmental. Oh yeah.
[00:13:28] Erica – The Hawaii Vacation Guide: Do use them?
[00:13:28] Jordan – The Hawaii Vacation Guide: Yeah. Yeah. We do.
[00:13:29] Erica – The Hawaii Vacation Guide: We do like to support local companies too. We have local companies on our website, but a lot of times we will go for the ease and the cancellation.
[00:13:38] Jordan – The Hawaii Vacation Guide: Yeah. ’cause there’s no prepayment with them. So you can always discount Hawaii car rental.
[00:13:41] Jordan – The Hawaii Vacation Guide: Right? Yeah. Honestly,
[00:13:42] Erica – The Hawaii Vacation Guide: they rates were so low the very first time you booked them. I thought it was a scam. Yeah.
[00:13:46] Jordan – The Hawaii Vacation Guide: That’s not good deals. I was
[00:13:47] Erica – The Hawaii Vacation Guide: like, what is this? Right. Yeah, but it, it saved us so much money.
[00:13:51] Jordan – The Hawaii Vacation Guide: And people love Costco Travel. That’s fun too. We love locals. Yeah. KeHE rent a car we always throw out to them on Maui.
[00:13:57] Jordan – The Hawaii Vacation Guide: Love them. Great family. Local family runs that. Joe’s, Jeeps on the big island. You know, we go local. We’ve even tried Turo. You know, you can try different stuff. Yeah. Stuff around. But we always say you never know where the deals are.
[00:14:08] Waikiki Without A Car
[00:14:08] Bryan Murphy: If we’re just doing Waikiki, like it’s just my wife and I, we’ll Uber over and then get a car for like the day do North Shore.
[00:14:15] Bryan Murphy: That’s the way to do it. Especially with parking in Waikiki. A lot of people don’t realize, yeah, there’s a lot of parking garages, but they’re expensive and if you’re trying to park at a hotel,
[00:14:25] Jordan – The Hawaii Vacation Guide: yeah, that’s, uh, no. We’ve done Waikiki trips without a rental car. That’s great. Yeah. And Oahu is the best island without a rental car.
[00:14:31] Jordan – The Hawaii Vacation Guide: Best public transport Circle Island towards, yeah. Lots of options. Right,
[00:14:35] Bryan Murphy: right.
[00:14:35] Island Drive Time Reality
[00:14:35] Bryan Murphy: Mistake number six kind of goes with this, talking about drive times across any of the islands, you know. Kind of picking on Maui a little bit. A lot of people stay in Ka Nepali and they want to do Rota, HANA, and it’s like, that is a huge drive.
[00:14:49] Bryan Murphy: Like you look at the map, you, you see your Kaho Lu and, and you’re like, oh, HANA is only like a 52 mile. Drive. Well, it’s obviously, it’s not a normal 52 mile drive. Narrow roads, one lane, roads, bridges, local traffic. That’s a whole other thing. So understanding that even on Kaia, I was talking my wife recently and we’re talking about, yeah, even trying to get to Poipu up to the, the lighthouse.
[00:15:15] Bryan Murphy: That is like, that’s a long drive
[00:15:19] Jordan – The Hawaii Vacation Guide: haul. Yeah, for sure. It’s a haul. I’ve always been getting bad too. It’s really, yeah, either road work or construction. It’s just a lot of reasons, but there’s, that was something
[00:15:26] Bryan Murphy: I noticed too. Yeah, yeah. Last time we were on, yeah, you get a cook view
[00:15:28] Jordan – The Hawaii Vacation Guide: highway and that’s it.
[00:15:29] Bryan Murphy: So drive type is a thing, and traffic is definitely something to prepare for if you’re staying in Honolulu or just.
[00:15:37] Bryan Murphy: Oahu in general. People commute in and out. Especially if you’re staying in Colina, there’s gonna be crazy YI traffic, depending on the time of day.
[00:15:46] Erica – The Hawaii Vacation Guide: That used to be my commute, and I used to have to leave at five in the morning from Colt. Oh my gosh. Downtown Honolulu. Yeah, and I was still in traffic. I would leave every morning at like 5 0 5 was my,
[00:15:55] Bryan Murphy: yeah.
[00:15:56] Bryan Murphy: I think it goes without saying the big island, Hawaii island, a lot of people stay in Kona and they want to do. Hawaii Volcanoes National Park, that is a epic drive of hour and a half, two hours. It took us like two hours stopping along the way. Yeah. Um, but yeah, that’s, that’s definitely, uh, be ready to, to think about.
[00:16:13] Bryan Murphy: Just be ready for that. Yeah.
[00:16:15] Weather App Misreads
[00:16:15] Bryan Murphy: Let’s move to safety and mistakes. This is something that’s super important and a lot of this is just, just unaware or just not. Knowing I, I think some of these other ones you can probably maybe figure out, but some of these things are just, you just gotta go to Hawaii and visit Hawaii to understand really what’s going on.
[00:16:31] Bryan Murphy: So mistake number seven, not understanding the weather. What would you say about that? This is an interesting
[00:16:36] Jordan – The Hawaii Vacation Guide: one and like, you won’t believe me until like you see it, but like, alright, so while people go to Maui. They’ll bring up Maui, like on their iPhone or something like that. Right. The weather app, you know, it’ll give you the weather for all of Maui with all the different ecosystems.
[00:16:50] Jordan – The Hawaii Vacation Guide: It’s going to be raining and cold somewhere on Maui, and it’s gonna show you that kind of like information so people freak out like, oh my God, it’s gonna be rainy all day in August. This is, this is not, what we recommend is like punch in exactly where you’re gonna stay, like on Ka Ali Wale Capua, and then see where the weather is there and, and then even then, it’s a tropical island, so it might have rain.
[00:17:09] Jordan – The Hawaii Vacation Guide: It might get a little windy, but it doesn’t mean your whole day’s gonna be like that. Mm-hmm. Now the big surprise was this last March and April when we had like two, you know, one Kona low store, two Kona lows. Yeah. Plus another storm. Yeah. And, uh, but then that goes into weather too. Like the mainland news made, made it pretty, seemed pretty bad on the islands and, and it was for shame.
[00:17:26] Jordan – The Hawaii Vacation Guide: A lot of locals and a lot of residents got hurt destroyed homes. But the visitor infrastructure wasn’t affected. Everything opened up again within a day. A lot of viewers told us, oh yeah, I had a great time. Like, you know, a couple days after the storm, the beach is cleared up, so Hawaii is, is open and welcoming visitors even after those big storms.
[00:17:43] Bryan Murphy: Rain in Hawaii is better than rain anywhere else in the world. It is. Yeah. You get the rainbows and stuff, right? Most of it is, is short. Obviously with the cornal nose, that was like almost like a once in a lifetime. Crazy
[00:17:56] Erica – The Hawaii Vacation Guide: what happened there. I really, yeah. I hope
[00:17:58] Jordan – The Hawaii Vacation Guide: it
[00:17:58] Bryan Murphy: was once a lifestyle. Yeah, I hope so too.
[00:18:00] Bryan Murphy: And, and depending on the side, side of the island, you know, if you are staying leeward side, like Colina, you’re probably gonna get drier weather, you’re probably gonna get more sun mm-hmm. Than if you’re staying in even, uh, maybe Hona loop. But if you’re staying in like Kai Lewis somewhere, or even up, you know, at North Shore.
[00:18:17] Bryan Murphy: You know, you’re, you’re gonna get a maybe a little bit more
[00:18:19] Jordan – The Hawaii Vacation Guide: wet. And the fun fact on Waikiki, it’s not even a tropical climate. They don’t get enough rain to be tropical. So like the rain, you’ll notice the rain just stops right before, like at H one before it gets to Waikiki.
[00:18:29] Start Hikes Early
[00:18:29] Bryan Murphy: Uh, mistake number eight. This is something that our first time going on, the Maka Poo Lighthouse.
[00:18:35] Bryan Murphy: Hike. We made this by starting too late, so starting hikes too late. The mokapu hike especially, it’s sunny. It can be very hot. Same with diamond head. That hike you want to do early in the morning. We got there like at nine 30. We, I mean, we had little, little kids at the time, so we’re just like. Made our way over from West Side to Maka and it was so hot pushing the stroller up.
[00:18:59] Bryan Murphy: What’s great about Ma Koo is, you know, it’s paved and you can mm-hmm. You can do the stroller thing. We started that hike way too late. So do your research on the hike that you want to do, especially those hikes over there that are, um, maybe those sunrise hikes you want to get there. Earlier rather than later.
[00:19:15] Jordan – The Hawaii Vacation Guide: We’ve been caught in that too with the Hot Days Cocoa head crater going up the Tramway with like a three-year-old. That was bad. That was
[00:19:21] Bryan Murphy: bad. Yeah.
[00:19:23] Swim With Lifeguards
[00:19:23] Bryan Murphy: Mistake number nine. Also, I had this on my list, is not swimming at Lifeguarded beaches and you see a beautiful beach. It doesn’t automatically mean it’s safe in an empty beach.
[00:19:34] Bryan Murphy: That should probably be a dead giveaway if you, if you come across an empty beach somewhere, that’s probably a good sign that you probably shouldn’t. Stop and get into the water, ocean conditions in Hawaii, they, they can change fast. Short break is real. It’s just different. Even if, you know, being in southern California, the waves are just different and the ocean is just different.
[00:19:54] Bryan Murphy: Reefs and southern drop-offs, those are dangerous and especially there’s plenty of lifeguards around all the islands, so just swim at lifeguard beaches. But having said that. There was another drowning at Hahan Bay recently that’s lifeguarded and you just gotta be super cautious and super careful going out and knowing what conditions are.
[00:20:16] Bryan Murphy: It’s the number one, if I’m not mistaken. It’s the number one cause of, of death is drownings for. Mm-hmm. And those are majority of visitors, unfortunately.
[00:20:25] Jordan – The Hawaii Vacation Guide: Yeah. Lifeguard beaches and, and go talk to the lifeguards. They’re super friendly, right? Like, and they got usually great stories too, but ask ’em like, Hey, what are the flags out today?
[00:20:32] Jordan – The Hawaii Vacation Guide: What are things to worry about? You know? Yeah. Safe place for my stuff.
[00:20:36] Erica – The Hawaii Vacation Guide: They would rather talk to you than rescue you later.
[00:20:39] Jordan – The Hawaii Vacation Guide: Yeah. You know? Oh, that’s a good, yeah. And, and yeah. And they do have some great stories. Like I met a lifeguard one time who, uh, he was, he was clearing fishing lines outta the rock in Maui, and he came up Uhhuh and he hit his head on something.
[00:20:49] Jordan – The Hawaii Vacation Guide: He’s like, oh man. Must have been a sea turtle. And it was like a eight foot tiger shark. Luckily the tiger shirt just swm away. But he is like, I lost it. I, he’s like, yeah. And then, then another guy on Oahu, he was a lifeguard. He had to take a break from his lunch shift so he could go win the Eddie, the big wave, big wave surf competition like a few years ago.
[00:21:06] Jordan – The Hawaii Vacation Guide: Right, right,
[00:21:07] Erica – The Hawaii Vacation Guide: right. Yeah. And that
[00:21:07] Jordan – The Hawaii Vacation Guide: was so cool. It was like a little local lifeguard, lifeguard guy, like beat out all these, all these dudes.
[00:21:13] Bryan Murphy: Yeah. Uh, Luke, I forget his last name.
[00:21:15] Snorkel Safety Basics
[00:21:15] Bryan Murphy: Mistake number 10 kind of goes with this, but ocean safety, going out, snorkeling when you’re not a strong swimmer. And this is definitely me.
[00:21:22] Bryan Murphy: I’m not a strong swimmer, so I do like the piddly, you know, lagoons and coline, and I’m just fine. Yeah. And it goes right away with what you’re saying.
[00:21:30] Erica – The Hawaii Vacation Guide: I just, we feel so passionately about this because people will email us all the time and they’re like, I’m not a good swimmer. I’ve never gone snorkeling.
[00:21:37] Erica – The Hawaii Vacation Guide: Where should I go? And I’m like, oh my God. Like I know you’re so excited to see this, but there are so many safe ways you can do this. Yes. Don’t go out by yourself. You can do a tour from a boat. We love boat snorkeling tours because they have somebody out there with you. They go over all the safety precautions, they’ll teach you how to snorkel safely, and then there are also snorkel towards.
[00:21:59] Erica – The Hawaii Vacation Guide: If you don’t wanna go on a boat, if that’s cost prohibitive or you just don’t like boats, for some reason they have snorkel tours that leave from the shore. So you have a guide taking you out so you can still have the experience but just mm-hmm. Safely, because you hear about so, so many drownings people either getting caught in a current just.
[00:22:18] Erica – The Hawaii Vacation Guide: You know, uh, it’s just, it’s really sad. It’s, yeah. Preventable.
[00:22:22] Jordan – The Hawaii Vacation Guide: As you mentioned, it’s the number one cause of death for, for, for visitors is, is drowning, but it’s number two for locals, so it’s the mighty Pacific Ocean. Mm-hmm. And it should never be underestimated. Yeah. It’s not like going in, you know, in a, an easy place.
[00:22:34] Jordan – The Hawaii Vacation Guide: So, yeah, we’re passionate about it. We always try to stay in all of our videos is, you know, only always snorkel the buddy. Endowed don’t go out. Yeah. You know, we, we have tons of slow saying that. We just try to help, help people know.
[00:22:46] Wrap Up And Next Part
[00:22:46] Bryan Murphy: All right, so I told myself I wasn’t gonna do this, but I’m gonna break this up in two parts as I was editing.
[00:22:52] Bryan Murphy: There’s just so much more. We went on talking for like another 30 minutes. So what I’m gonna do is I’m going to call this part one, and then next Tuesday I’ll be releasing part two of my conversation with Erica. And Jordan. So I hope this conversation has already given you so much to take away and, and help you with your planning.
[00:23:12] Bryan Murphy: And go ahead and hit follow on whatever app you’re listening to, and that way you’ll get notified next Tuesday for when part two will be released. So until then. As always, live with Aloha,
[00:23:30] Bryan Murphy: Mahalo 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. You can find all links and resources mentioned today in the show notes below. Hawaii’s Best is produced by Shore Break Media Group. Edited by Easy Podcast Solutions and with music by our friends.
[00:23:48] Bryan Murphy: Stick to you.
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Bryan Murphy is the creator of Hawaii's Best Travel and host of the Hawaii's Best podcast, a top-30 U.S. travel podcast with 650,000+ downloads and a 4.9-star rating from 280+ reviews on Apple Podcasts. A Certified Hawaii Destination Expert and member of the Hawaii Visitors & Convention Bureau, he helps visitors plan more meaningful trips to Hawaii with practical, respectful guidance. His work has been featured in Travel + Leisure, National Geographic, Yahoo!, Simple Flying, USA Today, Parents, and Fox.
