How to Build a Hawaii Itinerary That Actually Feels Like a Vacation

256_How to Build a Hawaii Itinerary That Actually Feels Like a Vacation

[00:00:00] Stop Overplanning Hawaii

[00:00:00] Bryan Murphy: I still catch myself doing this when I plan Hawaii. I look at an open spot in the itinerary and I think, “What else can I fit in there?” But sometimes the best Hawaii trips happen when you stop trying to add more, or better yet, taking something off the itinerary. And that’s what I wanna talk about today, how to build a Hawaii itinerary that actually feels like a vacation.

[00:00:21] Bryan Murphy: Aloha, and welcome to Hawaii’s Best. I’m Brian Murphy, Hawaii destination expert and your personal guide to planning an unforgettable trip to Hawaii. If you’re planning a Hawaii trip right now, you probably already know what I’m talking about. You have a list, maybe it started with one or two things you really wanted to do, then you started researching.

[00:00:40] Bryan Murphy: And suddenly, you have 40 things saved, restaurants, beaches, tours, lookouts, places you saw on Instagram, maybe some things that you’ve seen on my Instagram. And the hard part is most of those things are probably really good ideas, but that’s what makes this really difficult. You’re not choosing between something amazing and something terrible.

[00:01:02] Bryan Murphy: You’re choosing between something amazing and amazing, but you only have so much time and so much energy. And that’s what we’re gonna talk about today. I’m gonna give you a simple framework I use, and then I’ll give you a few questions you can use to look at the itinerary you already have, because honestly, you probably don’t need to start over.

[00:01:23] Bryan Murphy: You probably just need to edit.

[00:01:24] Who Is This Trip For

[00:01:24] Bryan Murphy: Before we talk about how much you should put into a single day, there’s a question that comes first, who is actually going on this particular trip? Because that changes how you do your itinerary. A trip with just me and Ali looks completely different than a trip with our three girls.

[00:01:41] Bryan Murphy: So anytime somebody asks me how much can we fit into a day in Hawaii, my answer is, it really depends. Are you traveling with kids? Are there grandparents involved? Is this a honeymoon, an anniversary trip?

[00:01:52] FOMO vs Real Vacation

[00:01:52] Bryan Murphy: I completely understand why people do this. We’ve done this before. Hawaii is expensive. You traveled a long way to get there.

[00:02:01] Bryan Murphy: Maybe this is your first trip. Maybe you don’t know when you’ll come back or if you ever will come back. So there’s this feeling that this FOMO feeling of missing out, we need to make every minute count. And that’s different between making every minute count and making every moment count. So I totally get it.

[00:02:18] Bryan Murphy: And I still do this. I’ll look at an itinerary and think, “Well, we’re already going to be on that side of the island.” And sometimes it can work, but sometimes that one extra thing is what changes the feel of the entire day and can snowball into the next day. One thing I’ve learned over the years is that some of my favorite Hawaii memories have been really the simple ones.

[00:02:42] Bryan Murphy: It’s a beach morning, pool in the afternoon, something good to eat, watching the sunset. Really, that’s it. That could be the entire day. And I think sometimes we feel like if we’re not consistently doing something, we’re wasting the trip. We’re wasting our money, you know? But that’s really not true.

[00:02:58] Bryan Murphy: Sometimes the slower pace is exactly what you came to Hawaii for and exactly what you and your group or your family really need.

[00:03:08] Plan the Whole Day

[00:03:08] Bryan Murphy: And this is probably the biggest mistake I see. People plan activities, but they don’t plan the actual day. So let me give you kind of an example of this. Say you book a snorkeling tour.

[00:03:18] Bryan Murphy: The tour says four hours. Great, you put it on the itinerary. The day is, it’s not four hours. You have to drive there, you find parking, check in, wait for things to start, do the tour, get everybody back together afterwards. Then you gotta figure out food, drive back. That four-hour activity might actually take up most of your day right there.

[00:03:37] True Time Cost

[00:03:37] Bryan Murphy: And this is especially important in Hawaii because things can feel much closer on a map than they actually feel. I’ve talked about this before. Drive times across island are a thing. Maybe you wanna stay longer. Maybe parking takes longer than you thought and you, you keep circling and circling. Maybe lunch takes longer.

[00:03:54] Bryan Murphy: Those moments are a part of really life, but those are part of Hawaii. Hawaii can just kinda move at its own pace sometimes. But if your itinerary is packed and you’re constantly thinking, “We have to leave. We have to get back. We, we got the luau, we gotta get to.” So the question I want to really ask you with every activity that you put on the itinerary is what is the true time cost?

[00:04:14] Bryan Murphy: Not just how long does this activity take, you know, the drive time and all the stuff in between that we talked about.

[00:04:19] Anchor Add On Flex

[00:04:19] Bryan Murphy: So how do you actually build a day? And this is the framework I’ve used year after year, all the trips we’ve taken over 30 or so. Anchor, add-on, flex. The anchor, you wanna start with the thing that matters most.

[00:04:32] Bryan Murphy: What is the one thing your group would actually be disappointed to miss? Is it Pearl Harbor, Haliakala Sunrise, Rodahana? Is it Nepali Coast on Kua’i? Those are like anchors. That’s your anchor activity. I think you can use that same idea every day. What is the thing this day is built around? Because once you know that, the rest really gets a lot easier.

[00:04:54] Bryan Murphy: And then comes the add-on. Then look for things you can naturally fit in around that anchor. So a keyword is naturally, not what else can I squeeze in? Instead, since we’re already here, what makes sense? So for example, Pearl Harbor, it’s your anchor. Maybe you spend more time around Honolulu that day, but maybe you go explore another area nearby.

[00:05:15] Bryan Murphy: So what I probably wouldn’t do is finish Pearl Harbor and immediately think, okay, now let’s drive to the North Shore, hit a beach, get some food, and make it back in time for dinner in Waikiki. Could you do that? Probably. But would I want that to be my vacation day? Probably not. All right. And then here’s the, the third component of this is the flex.

[00:05:37] Bryan Murphy: You got the anchor, the add-on, and now the flex. These are the things that would be great if they happened. But if they don’t, the day is still a success. So maybe that’s shave ice, maybe it’s walking around and shopping in a beach town. And honestly, this is the hardest part for planners. You have to be okay with not doing everything because skipping something does not mean you failed.

[00:06:02] Bryan Murphy: It does not mean that the trip was a failure. It means you chose to do what mattered most.

[00:06:08] Geography and Areas

[00:06:08] Bryan Murphy: The other thing I would look at is geography because this is where a lot of people really get stuck. They create a list of the best things to do, but they don’t think about where those things actually are on the island.

[00:06:22] Bryan Murphy: You can have an amazing list and still create a frustrating trip, especially on Oahu, Diamond Head, Pearl Harbor, North Shore, Windward Coast, Koolina, those are all great, but they don’t necessarily belong together on the same day. So a better question is, since we’re already here, what makes sense? That’s why I like planning by area, the area of the island that you are spending time on.

[00:06:46] Bryan Murphy: You’re spending less time in the car, you’re less rushed, and you actually enjoy the places that you come to see. You came all this way to see and experience.

[00:06:54] Pressure Test the Week

[00:06:54] Bryan Murphy: And really one final thing, don’t just pressure test the day, pressure test the entire week if you’re staying seven days or the entire length of your stay in Hawaii because one busy day might be totally fine.

[00:07:05] Bryan Murphy: You’re gonna probably have a busy day. The problem is when every day is that busy. So look at your itinerary and ask how many early mornings do we have? How many early mornings do we want? And if you’re gonna do early mornings, you probably wanna do them at the beginning of your stay because of the time change.

[00:07:22] Bryan Murphy: And how many long drives do you want? How many days will you absolutely have to be somewhere at a certain time, like Aluau, for example. One sunrise at Haleakala might be amazing. You wake up at 3:00 and you do it, but three early mornings in a row might feel very different. One big adventure day is great.

[00:07:40] Bryan Murphy: Seven adventure days without breathing room might not be. But again, goes back to what type of trip do you want for this trip?

[00:07:48] Leave Room for Hawaii

[00:07:48] Bryan Murphy: And this is probably the biggest thing I’ve seen and have learned over time, sometimes from the hard way, is leave room for Hawaii to happen. Some of the best moments are the things you didn’t plan.

[00:08:00] Bryan Murphy: Maybe you, you find a beach you love, maybe somebody recommends a restaurant, maybe your kids want to stay a little bit longer at the pool, or maybe they wanna go back to that restaurant that you discovered and you don’t wanna miss that opportunity. And that’s okay because one of the best things you can do on a Hawaii vacation is give yourself permission to enjoy where you already are.

[00:08:22] Wrap Up and Free Checklist

[00:08:22] Bryan Murphy: So thanks again for listening to Hawaii’s Best. If you wanna grab the free itinerary reality checklist, you can go to hawaiisbesttravel.com/256guide or just easier go to show notes below. All right. So until next time, as always, live with Aloha.