Hawaii Travel Podcast by Hawaii’s Best: Hawaii Travel Tips, Things to Do in Hawaii & Vacation Planning

Most People Plan a Hawaii Trip Backwards. Here’s the Right Order

• Bryan Murphy - Certified Hawaii Travel Expert & Creator of Hawaii’s Best Travel • Episode 251

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Are you planning your Hawaii trip in the wrong order without even realizing it?

👉 Start planning with the Hawaii Trip Planner Hub

Most people start with flights or a bucket list, and that's actually backwards, it just leads to stress and wasted money.

Hit play now and get the exact 8-step order that takes the guesswork out of planning your Hawaii trip.

If you've ever wondered what to actually do first when planning Hawaii, this episode is for you. I'll walk you through the order that actually works, from picking your island to locking in the right reservations.

In this episode of Hawaii's Best, we break down the right order to plan a Hawaii trip so you can avoid costly mistakes and actually enjoy the process.

👉In this episode, you will:

  • Learn why picking your island should come after deciding what kind of trip you want, not before
  • Discover which few reservations can control your whole itinerary and need to be locked in early
  • Find out why pricing the whole trip, not just the flight, saves you from budget surprises later

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Scroll up ⬆️ and hit play now to plan your next Hawaii trip in the right order, start to finish.

🤙 Resources mentioned:

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🎧 Related episodes:

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💻 Related blog posts:

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🤓 Chapters:

  • 1:11 Step 1 Define Your Trip
  • 3:42 Step 2 Pick the Island
  • 4:54 Step 3 Shape the Details
  • 6:07 Step 4 Price the Whole Trip
  • 7:23 RedWeek Lodging Hack
  • 8:29 Step 5 Book the Big Stuff
  • 9:42 Step 6 Anchor Reservations
  • 10:49 Shaka Guide Explore More
  • 11:51 Step 7 Build Your Itinerary
  • 13:15 Step 8 Final Reality Check
  • 15:29 Closing and Next Steps
Self-Guided Island Tours
Change The Way You See Hawaii with SELF-GUIDED AUDIO TOURS

Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.

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🌴 Plan Your Hawaii Trip With Bryan

About Your Host: Bryan Murphy is the founder of Hawaii’s Best Travel & a Hawaii Destination Expert through the Hawaii Tourism Authority, since 2020. An HVCB member since 2019, he helps first-time & repeat visitors plan respectful Hawaii vacations w/ clear, practical advice & cultural insight.

🤝 To sponsor the show visit hawaiisbesttravel.com/partner

Hawaii travel podcast helps you plan a trip to Hawaii with clarity. Discover practical travel tips, island itineraries, & local insight to help you explore Oahu, Maui, Kauai, the Big Island.

Edge of the Ocean (w/ permission)
Ukulele and Chill (w/ permission)
Talk Story (w/ permission)

251_Plan Hawaii in This Order


[00:00:00] Stop Planning Backwards

[00:00:00] Bryan Murphy: A lot of people plan Hawaii backwards, and honestly, I still do too sometimes. I'll catch myself checking flights before I've even figured out what kind of trip we want, what island or anything like that. So today, let's fix that and go through the right order to plan your trip to Hawaii. Aloha and welcome to Hawaii's Best.

[00:00:19] Bryan Murphy: I'm Brian Murphy, Hawaii destination expert and your personal guide to planning an unforgettable trip to Hawaii. And today I wanna help simplify Hawaii planning because I think the problem for people, it's not a lack of information. There's like way too much information out there. You've probably got saved Instagram posts.

[00:00:38] Bryan Murphy: Maybe some of my Instagram posts are saved on your phone, Reddit threads, YouTube videos, browser tabs. I have tons of browser tabs open all the time. That's how I survive. I don't know. I just always have so many browser tabs, but maybe that's you. You have tons of browser tabs open as you're trying to plan.

[00:00:54] Bryan Murphy: But what do you actually do first? Because the order really does matter. And I've learned that both from helping people plan Hawaii trips and also from making plenty of my own mistakes along the way after some 30-some trips to the island.

[00:01:11] Step 1 Define Your Trip

[00:01:11] Bryan Murphy: So let's start at the beginning with step number one is figure out what kind of trip you're actually wanting to take.

[00:01:18] Bryan Murphy: So before you even choose an island, start with who's going? Like the, who, who are the people going and what kind of trip do you want? What does a collective group want out of that trip? And this changed a lot for my family over the years. You know, a trip with just Allie and I, my wife, that can look completely different than taking a trip with our three girls, two of which are now teenagers.

[00:01:44] Bryan Murphy: That's a lot of fun. And that looks, you know, completely different again than going with my in-laws. And even as our girls have gotten older, the way we plan has changed quite a bit. I think in a good way, it's been a lot more simplified. There are experiences I, as I look back now and think, yeah, we probably did a little too much too young.

[00:02:05] Bryan Murphy: For example, Pearl Harbor is one of those things I think we did a little too young. One time we went, we had a very active three-year-old and a pretty timid five-year-old and a baby who was only a few months old. So we had, like, we're playing man-to-man defense. We had at least one adult per child. So we though we, you know, had it on control, but not really.

[00:02:28] Bryan Murphy: Looking back, it was still a good trip, but it was pretty stressful at a lot of times during that time at Pearl Harbor. Some wanted to do certain things, and some were too scared, and not everyone wanted to do the boat ride over to the USS Arizona Memorial. And honestly, putting our very active three-year-old on that experience wasn't probably gonna be a good idea anyway.

[00:02:50] Bryan Murphy: And, and Elle, our three-year-old at the time, was very active and strong-willed. Well, I guess she kinda still is. But Pearl Harbor itself wasn't the problem. It was just the season of life we were in. And that's why I think one of the worst questions to start with is what are the must-do things in Hawaii?

[00:03:09] Bryan Murphy: There's lists everywhere. There's podcasts about it, all that. And, and I think the biggest thing is to start with what makes sense for us on this trip? And I think this, that word is important because this trip may look different than the next trip. And, you know, are you gonna go with young kids, teenagers, grandparents?

[00:03:29] Bryan Murphy: Is this a honeymoon? An anniversary? Do you want to explore all day? Or are you happily just spending half the day at the pool and lounging around? So figure that part out first in step one.

[00:03:42] Step 2 Pick the Island

[00:03:42] Bryan Murphy: Moving to step two is then choose the island that fits that trip that you're wanting to do. So it's not necessarily, like, your favorite island.

[00:03:51] Bryan Murphy: You wanna choose the island that fits this particular trip. Oahu gives you plenty of variety, beaches, history, food, Waikiki, and the North Shore, West Side, Koolina, plenty of great places around the island of Oahu. Maui gives you a great mix of both resort time, beaches, scenic exploring, some road trips.

[00:04:14] Bryan Murphy: Kauai tends to work well for slower, more nature-focused trips. Then you have Big Island, Hoi Island, which gives you Volcanoes National Park, huge landscapes, a lot of driving. So think of that. If you have young kids, it's gonna be a drive from Macona over to Hawaii Volcanoes National Park. It's gonna at least be an hour and a half, maybe two hours.

[00:04:36] Bryan Murphy: But you could have an amazing trip on any of those islands. The question is, which fits the people, the group, giving. Again, go back to who's going on this trip. What fits that group that you're traveling with and the kind of trip that you're hoping to do right now in today's stage of life?

[00:04:54] Step 3 Shape the Details

[00:04:54] Bryan Murphy: Step three is then to figure out the shape of the trip.

[00:04:57] Bryan Murphy: So meaning, like, how much do you actually have to spend on this? Maybe it's just gonna go on the credit card or whatever. Been there, done that. But what time of year are you going? How many nights are you gonna be on island? Are. Do you want to island hop? Is it one island or two? Or three? Please don't try to do three if you're not staying three weeks.

[00:05:16] Bryan Murphy: And just a quick, if you are gonna island hop, I'd highly recommend if you can at least do at least 10 days minimum. But two islands, especially traveling as a family, within seven days is, is pretty tight, and I've done episodes on that I'll link below. But this is, I think, where I'd be careful about trying to do, you know, too much, because every island change, it costs you, will cost you money.

[00:05:37] Bryan Murphy: You'd be surprised how expensive some, uh, inner island flights are now. But every island change costs you time. So you gotta pack up, check out, return the car, you know, go to the airport, fly another rental car, check in again. That might not sound like much, but when you're looking at the itinerary from home, that might not sound like much, but while you're there on island, it eats up a lot of precious vacation time.

[00:06:02] Bryan Murphy: So decide the basic kinda shape of the trip before the calendar fills up.

[00:06:07] Step 4 Price the Whole Trip

[00:06:07] Bryan Murphy: And then step four, price the whole thing. Price the trip. Now, this is the part I'm guilty of. I still do this is flights. I check. I love checking flight prices. I don't know what it is. I'm always dreaming about getting back over to Hawaii.

[00:06:21] Bryan Murphy: So I'll start moving dates around, checking different airports, seeing what Hawaiian Airlines is currently doing. And suddenly, I'm mentally booking a trip that we haven't even planned for. There's nothing wrong with that. It's always cool to, like, dream and just see where things are at. So there's nothing wrong with checking airfare, but just don't let the airfare make the whole decision on your entire trip, because a great price on a flight doesn't mean much if lodging for those dates is way over your budget.

[00:06:51] Bryan Murphy: So instead of pricing the flight, price the trip. So from airfare, lodging, rental car, parking, food, tipping, activities, taxes, fees, get a rough idea of what the whole thing actually looks like before you start locking in that flight. And you, you think about, you know, where you're staying too. Saving a little bit on your hotel isn't necessarily a deal if you're gonna be spending half the trip driving back and forth across the island, or you're gonna be, you know, eating out every single night.

[00:07:23] RedWeek Lodging Hack

[00:07:23] Bryan Murphy: And since lodging is usually one of the biggest, it's actually the biggest part, typically, of a Hawaii budget, this is a great place to tell you a little bit about today's sponsor, and that's Red Week. My family and I, we've been staying at Marriott's Coalina Beach Club on Oahu for over 20 years now, which is wild to think about.

[00:07:42] Bryan Murphy: And one of the reasons that it works so well for us is the space. You have a full kitchen, laundry, more room for everyone, plus the pools, and the calm Coralina Lagoons right there. And I think what a lot of people don't realize is that it's also a timeshare resort. And when owners aren't using their weeks, some list those weeks for rent on Red Week.

[00:08:01] Bryan Murphy: So you don't have to own a timeshare to stay at a Timeshare resort, which is pretty cool. And the best place to look is at redweek.com for current listings. Check them out. They're across all the islands. And again, it doesn't hurt to look just to see where prices are at. I think you'd be surprised that you could save quite a bit of money on a great location and a great resort that maybe wasn't even on your radar.

[00:08:25] Bryan Murphy: So go ahead and check current availability at redweek.com.

[00:08:29] Step 5 Book the Big Stuff

[00:08:29] Bryan Murphy: And then step number five, booking the big things happens. Once you know what the trip looks like, you start locking it in, flights, lodging, rental car, if you need one. If you're staying in Waikiki, you may not need one. Everywhere else, you usually do.

[00:08:44] Bryan Murphy: Just because I told you, you know, not to start with flight doesn't mean you need to wait forever to book. And we made this mistake recently on our last trip. We were flying during Christmas break, and I think I waited until, like, six weeks out to finally book everything, or the flight at least. Like, whoops, we're a family of five.

[00:09:02] Bryan Murphy: And by that point, we weren't gonna be sitting all together. So two of us were in one part of the plane, three of us were in another. It was fine. But if our girls were littler, it would've been even tougher. You know, lesson learned. But it was also one of those moments where I though, Brian, come on, you literally share with people how to plan trips to Hawaii.

[00:09:22] Bryan Murphy: So yes, I'm still learning and making mistakes and I get to pass those lessons onto you. So the point is, don't let airfare choose the trip before you've done the other work. But once you know when and where you're going, especially during busy travel periods, don't wait too long either to pull the trigger.

[00:09:42] Step 6 Anchor Reservations

[00:09:42] Bryan Murphy: And step six is find the things that could control the schedule. So before you build out every day, identify the few experiences that could dictate your itinerary. So maybe it's Hayanna State Park on Kauai, Haliakala, Sunrise, Pearl Harbor, Wayanapanapa on Maui, a specific luau that might sell out. It's a, maybe it's a boat tour.

[00:10:05] Bryan Murphy: Whatever it is, whatever your family really wants to do, you know, get their input. Some Hawaii experiences have reservation windows that open weeks before your trip. Others can sell out really fast. So I'd pick maybe two or three of those things that really matter and have those become your anchors, like the things that are just, they're in pin on that itinerary.

[00:10:28] Bryan Murphy: And, you know, you don't have to know where you're eating lunch three months from now. You just need to know which things you can't afford to miss the booking window for, then build around those other activities that you wanna do. And once those anchor days are figured out, I like leaving room to explore the island.

[00:10:49] Shaka Guide Explore More

[00:10:49] Bryan Murphy: And that's w - one of the reasons I've used Shaka Guide for years now. And what's really cool is that they're also a sponsor of today's episode, Shaka Guide, is a GPS-based audio tour app with turn-by-turn directions, local stories, history, and stops along the way. Even music is c - pretty cool. And as a personal note, I've actually worked really close with a team at Shaka Guide for years now, long before this current partnership.

[00:11:12] Bryan Murphy: And one thing I've always appreciated is their attention to detail. They put so much detail and accuracy in their tours, and I like being able to explore on my own pace, not necessarily like with the tour group. So that's why I love the tours that they've built. Uh, they're available on all the islands.

[00:11:28] Bryan Murphy: So any tour, anything you can think of, Shaka Guide has a tour for that. So you can simply check them out at hawaisbesttravel.com/shakasummer. And you can also just use a code Hawaii's best at checkout for 15% off all tours and bundles. And Shakaguide is actually across the US, which is really cool. So check out what they got going on over there at ShakaGuide.

[00:11:51] Step 7 Build Your Itinerary

[00:11:51] Bryan Murphy: So step seven, now it's time to build that itinerary, your 47 tabs or whatever you have open. Now you can finally use those saved posts, start filling in the dates around your anchors, but keep it simple. We like to do, like, one main thing per day. It's usually plenty. So group things geographically and be realistic about time drives.

[00:12:11] Bryan Murphy: You might be surprised that a few miles on the map in Hawaii could be an hour, you know, like, "Oh, it's just on the other side of the island. It doesn't look that far." You'd be surprised. So leave some time and space for that. This is really one of the easiest mistakes, and I see this mistake over and over from the people I talk with, is making sure you have buffer for those drive times.

[00:12:33] Bryan Murphy: And some of our best family days have been pretty basic, pretty quiet. Beach, pool, something to eat. Monkeypod kitchen is usually always somewhere in there. Sunset, that's pretty much it. We're, we're really simple, I think, as, you know, if you see our itinerary, uh, we don't have much of an itinerary. You know, we, we plan a few things here and there, but we'd like to keep it simple and just kind of go at the pace of where everyone's at and where the island's at.

[00:13:01] Bryan Murphy: So the goal isn't to just prove how many things you can fit into a Hawaii vacation like it's Disneyland or anything. It's actually to be able to enjoy your time there and to recharge and, and really create and build those memories.

[00:13:15] Step 8 Final Reality Check

[00:13:15] Bryan Murphy: And then step number eight, do one final reality check. You know, before you leave, check the plan again.

[00:13:22] Bryan Murphy: Are your reservations confirmed? Are there any closures that can happen? We're seeing a couple closures right now. Hanama Bay is one of those closures. Eah Valley was slated to open today on August 7th at the time of this recording, and so far, it's not. So be aware there are some closures, weather issues, ocean conditions.

[00:13:44] Bryan Murphy: Do you have backup plans if anything changes? Are you trying to drive too far one day? Do you have places on the itinerary that are private or off limits? It's important that, to check that out because that's an im- important thing about being a responsible visitor to Hawaii is just knowing what is off limits, because that's important for culture and for locals and Hawaiians to make sure that we're traveling into places that are okay too.

[00:14:10] Bryan Murphy: And honestly, sometimes the best thing you can do for your Hawaii itinerary is to delete something. You can always come back, right? At least that's what I tell myself.

[00:14:20] Trip Planner Hub Wrap Up

[00:14:20] Bryan Murphy: This whole process is really. I've had this secret project for. A couple of you know who listened to this podcast, but I've had this secret project for a few months and it's the Hawaii Trip Planner Hub because I've kept seeing the same problems, myself included.

[00:14:35] Bryan Murphy: I wish I had this years ago. People usually don't necessarily need more Hawaii information. They need help turning all that information into an actual plan. So the Hub, it walks you through these decisions in order. Which island fits your trip. This trip, what are your dates, your trip length, a realistic budget, what needs to be booked early?

[00:14:54] Bryan Murphy: Reservation reminders, yes, you can download reservation reminders on your calendar and then it pops up, "Hey, go book Hanama Bay." You can build your itinerary and tools that help catch some of those common planning mistakes before you even get on island. Brings everything together in one actionable plan instead of having everything scattered across with like screenshots and browser tabs and random notes.

[00:15:16] Bryan Murphy: So if you're planning a Hawaii trip right now or you're thinking about it and want something to walk you through this whole process, check out the Hawaii Trip Planner Hub. It's the first link in the show notes below. We're loving to know what you think about it.

[00:15:29] Closing and Next Steps

[00:15:29] Bryan Murphy: So that's what I have for you on this episode.

[00:15:31] Bryan Murphy: Everything that I talked about, Red Week, Shaka Guide, the Hawaii Trip Planner Hub, everything, all that will be linked below and also relevant podcast episodes that might be a good next step for you in your planning. You can check out below in the show notes. So until next time, as always, live with Aloha.

[00:15:54] 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.


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