Our Oahu Family Itinerary: 7 Nights in Ko Olina

266_Steal My Family’s 7-Day Hawaii Itinerary for Oahu (What I Skipped and Why)

[00:00:00] Family Oahu Trip Preview

[00:00:00] Bryan Murphy: Today I’m gonna share with you what made the cut, what we’re doing this January as a family multi-generational trip to the island of Oahu. Plus, I’m also gonna give you a couple other itineraries that’ll help you with your planning to Oahu. Aloha and welcome to Hawaii’s Best. I’m Brian Murphy, a Hawaii destination expert and your personal guide to planning a better Hawaii trip.

[00:00:22] Bryan Murphy: Through practical tips, local voices, and stories from the islands, I’ll help you make the most of your time in Hawaii and stay connected between visits. So we’re heading to Oahu again this January, early January. For a week, it’s gonna be Ali, me, our three girls, and my in-laws, so seven of us, three generations.

[00:00:41] Bryan Murphy: And if you’ve ever done a trip, you ever tried to plan for a trip with a group like that, you know it can get pretty complicated pretty quickly. Everyone has their own interests, what they wanna do, what they’ve envisioned this trip to be. Been there, totally understand. And some people, you know, they want to explore more.

[00:01:00] Bryan Murphy: That’s like my brother-in-law, he likes to get out there. And others want to find more time to relax. That’s me, that’s Ali. And then there’s, of course, trying to figure out where everybody wants to eat. You only have a certain amount of days in Hawaii. Now, a couple episodes ago, just last week, episode 264, I shared the seven decisions that I make before booking a trip to Hawaii.

[00:01:24] Bryan Murphy: Things like figuring out who you’re actually traveling with, choosing the right island for your home base, and building your itinerary around the activities that matter most to you for this specific trip. Well, I’ve been using that same process to plan countless of trips to Hawaii. I use it for clients that I help coach plan their trips for.

[00:01:45] Bryan Murphy: And I thought it’d be helpful to walk you through how I actually do this, how I actually came up with this itinerary that we’re gonna be doing in January, because there’s a difference between talking about how to plan a vacation and actually making those decisions for your own family. So though it’d be cool for this episode to give you kind of a behind the curtains look at what the Murphy family, what we’re doing for our Oahu trip.

[00:02:08] Trip Goals and Constraints

[00:02:08] Bryan Murphy: Before I start filling in restaurants and attractions, I had to think about the kind of trip that we actually want. We’re traveling with seven people across three generations. We also have a birthday during the trip, which is our youngest daughter. So for this vacation, Oahu gives us a good mix of things our family really enjoys.

[00:02:31] Bryan Murphy: Our girls are older now. They wanna do Pearl Harbor. We wanna get in some Hawaiian history. We gotta do the North Shore. There’s some great restaurants we wanna make sure we do. And plenty of opportunities to spend time together and relax. But here’s something else I had to consider. We’re staying seven nights.

[00:02:49] Bryan Murphy: Wish we were staying more, but we’re doing seven. That doesn’t mean it’s seven full vacation days, as you probably know. Once you account for arrival and departure, we’ve really got like six full days to work with.

[00:03:01] Home Base and Drive Times

[00:03:01] Bryan Murphy: And I, I don’t want all six of those days to be packed with sightseeing, especially because we’re gonna be staying at Marriott’s Colina Beach Club that’s over on the west side, Kapule area.

[00:03:13] Bryan Murphy: So our girls love it there. We love it there. So they love the pools there, the beach, the lagoons, the different activities that Marriott puts on throughout the week, you know, from bingo to, to the slide races, all those things that they’re a good resort kinda hosts while you’re there. So if we’re spending every day driving around O’ahu, we’re missing out on something that’s actually pretty important for our family.

[00:03:37] Bryan Murphy: Again, it goes to like, what do you want for that trip and what you want for your family? But here’s the trade off. Being that Kolina is on the west side o- of Oahu, getting to Honolulu takes, it could take around 35 minutes on a good day. That’s what, you know, traffic is light and it takes longer when it’s busy.

[00:03:55] Bryan Murphy: Also getting up to Haleiwa on the North Shore is roughly 40 minutes without much traffic. But we are going during the wintertime, so there is a chance if there is a good swell coming in that we could hit some traffic because of people maybe going up to watch the surfers. Maybe there’s gonna be a surf competition.

[00:04:13] Bryan Murphy: You just never know during the wintertime on the north shore of Oahu. And oh, by, by the way, if you’re staying in Waikiki, your itinerary might look completely different. You could spend more time exploring Honolulu without having to make these longer drives. So that’s why I always recommend choosing your home base before you start filling in your days.

[00:04:33] Bryan Murphy: The same things to do can make for, you know, two very different vacations depending on where you’re staying. Staying in Hilo is completely different than staying in Kona. And same thing for like Kauai. If you’re staying North Shore, that’s gonna look completely different than staying in Poipu down in the South Shore.

[00:04:51] Bryan Murphy: So for us, Kolina makes the most sense because we want that resort time, but it also means we’re going to group our activities together instead of constantly driving back and forth across the island. You gotta answer the question of what kind of vacation are you planning? Who’s going? What do you wanna do?

[00:05:07] Bryan Murphy: Where are you gonna stay?

[00:05:08] Book These First

[00:05:08] Bryan Murphy: And then the second question you gotta answer is what do you need to book first? And once I had the basic structure figured out of what type of vacation we want for this trip, I started looking at the things we really wanted to do. And more importantly, which ones needed reservations.

[00:05:23] Bryan Murphy: Pearl Harbor, like I mentioned, is one of those priorities. It does require reservations. So we want to visit the USS Arizona Memorial, and we’re also gonna do the Aviation Museum over on Ford Island as well. Now, if you’re planning to visit the Arizona Memorial, there’s something important to know.

[00:05:38] Bryan Murphy: Currently, reservations are released eight weeks in advance with another release 24 hours in advance. So that’s something you definitely wanna plan for. I actually have a handy dandy reservation checker for free that you can get in the link below. You type in your, your dates and what you wanna do on which island.

[00:05:56] Bryan Murphy: Then you can download a calendar reminder and it’ll prompt you and remind you, “Hey, go book it.” So we also wanna do Ilani Palace and we’re also planning a sunset sale out of Cotolina, out of the marina there. Now, one little wrinkle with that is that the operator requires at least eight passengers for the cruise to run.

[00:06:16] Bryan Murphy: We’re seven, but I think it’s just gonna be five of us doing this sale. So I need to confirm that, what that looks like before anything else. And then there’s our daughter’s birthday and we’re gonna do that. We have dinner planned for Monkeypod Kitchen. So there’s another reservation that we need to get on the calendar.

[00:06:33] Bryan Murphy: Here’s how I approach this for your trip. First, figure out which activities have limited reservations. And then second, look at anything tied to a specific date, like a birthday dinner, anniversary, anything like that. And then worry about smaller activities that are easier to move around and always double check current booking requirements before making, you know, any solidifying your plans.

[00:06:58] Bryan Murphy: So once I identified those priorities, here’s how the actual week started coming together. Our actual itinerary is this right here.

[00:07:06] Arrival and Resort Day

[00:07:06] Bryan Murphy: Sunday is our arrival day. We’re gonna be heading to Ko’olina and then get settled in to our villa. We got a three bedroom this year. Really excited about that. And probably do a grocery run.

[00:07:18] Bryan Murphy: Honestly, we’ll probably end up at Costco. That’s what we usually do. So with seven of us, we’re planning to eat breakfast in the villa throughout the week. It’s easier. We call them Papa Jack’s sandwiches, so we’re gonna be doing that. It’s easier and it’s one less thing we have to figure out every morning, just keeping mornings simple, starting a little bit slower is how we like to roll.

[00:07:38] Bryan Murphy: And then we’re planning on doing dinner at Monkey Pod that night. That’s our first meal when we get there is we hit up Monkey Pod. And apparently we’re just gonna keep that tradition going because we, I gotta get those Bogogie tacos and the Mai Thais and yeah. So Monday is mostly gonna be a resort day.

[00:07:58] Bryan Murphy: We’ll have breakfast, enjoy the pools, probably do slide races and see what other Marriott activities the girls want to do. There’s usually a preview night for Fia Fia, which is Chiefs Lu’au. They come over from the water park and they do a preview, which is pretty cool. And then Tuesday, they have the Fia Fia Luau on property at Marriott, but we’re not gonna do that, but it’s cool to see the preview Monday evening.

[00:08:21] Bryan Murphy: Later that afternoon, we’re hoping to do that sunset sale out of the marina there. So we’ll see if we can make that happen. And if not, we’ll probably end up at Monkey Pod. But we’re not driving across the island on Monday just to do a boat cruise or anything like that. So we’ll see how this plays out.

[00:08:39] Bryan Murphy: January is also whale season in Hawaii, so we’ll see what happens. You just never know. But that’s not why we’re gonna be booking it. We’re just really looking forward to getting out on the water together. I think this is something special for our girls, especially for our youngest, her birthday.

[00:08:54] Pearl Harbor Anchor Day

[00:08:54] Bryan Murphy: Okay, so Tuesday, uh, we’re planning Pearl Harbor on Tuesday.

[00:08:57] Bryan Murphy: We’re planning on doing the Arizona Memorial and the Pearl Harbor Aviation Museum. Actually have, had the CEO of the Aviation Museum on the podcast. I’ll drop that episode link below, but we’re gonna be going over there on Tuesday. That’s gonna be most of the day. Like I mentioned, you wanna do like an anchor day.

[00:09:15] Bryan Murphy: That’s what I mentioned in episode 264. You wanna have that anchor day and then we’re gonna do some stuff around Pearl Harbor. But we don’t wanna make it rush, especially with our girls. I wanna have some time to learn about the history, for them to experience it, to be able to slow down. And after that, we’ll probably maybe tinker around that area.

[00:09:35] Bryan Murphy: But more than likely, we’ll just head back home, head back to Cotolina or stop off for dinner at California Pizza Kitchen. Uh, I know it, there, there’s one in, in Kapolei and you’re like, CPK, you’re in Hawaii. But our girls love it. It’s one of those meals. Y- you know, you have those meals if you’re a family.

[00:09:51] Bryan Murphy: You have those meals where everybody can get something they like and CPK happens to be one of those spots that there doesn’t seem to be a lot of disagreement about. So we’ll probably do that one night. Everybody can find something they like there. And then we’ll catch a sunset in, you know, one of the lagoons and we’ll call it a night.

[00:10:09] North Shore Winter Day

[00:10:09] Bryan Murphy: Wednesday is gonna be our North Shore day. We’ll leave Cotolina in the morning. We’ll probably do a pit stop at Dole Plantation, maybe grab some Dole Whip. We don’t do much there anymore. Hit the bathroom and then keep on heading up to the North Shore, do the North Shore Soap Factory. We always stop at that in Wailua.

[00:10:27] Bryan Murphy: So look forward to checking in there. Maybe say hi to Debbie, the owner there. She’s also was on the podcast. I’ll give them a shout out and drop our episode below as well. And then there’s a newer Island X there, kinda same complex where the North Shore Soap Factory is. We’re gonna probably stop off there too, some cool little shopping there.

[00:10:47] Bryan Murphy: And then make a way to Haleiwa and we’re planning on doing lunch at Halewa Beach House and followed by some exploring throughout the town. Maybe we’ll stop at a beach or two, depending on how everyone’s doing, depending on if it’s crazy or if there’s a surf competition going on. That might scratch our entire day, but we’ll keep it flexible.

[00:11:06] Bryan Murphy: And when I mention about like stopping at a beach, we’re not gonna get in the water. You do not wanna get in the water in the North Shore during the wintertime. It’s just too unpredictable and the waves are just crazy. Like it’s, you can feel it from the shore, like just how intense some of the waves are.

[00:11:20] Bryan Murphy: So if anything, we’ll just watch from afar. But the more I looked at this day, I, I originally had though doing the sunset sale plan for this day, but the more I looked at it, the less it made sense. We’d spend the entire day watching the clock and I was like, I tell people not to do that. That just was not something we wanted to stress about.

[00:11:41] Bryan Murphy: That’s why I moved it over to Monday. Now, Wednesday is our North Shore, that’s our anchor is North Shore Day.

[00:11:48] Birthday Plans Flex Day

[00:11:48] Bryan Murphy: And Thursday, now Thursday’s a special day because that’s our daughter’s birthday. This one is honestly up in the air. We’re, we know that we’re gonna end up at Monkeypod, that’s where she wants to go for her birthday dinner.

[00:11:59] Bryan Murphy: We’re just gonna leave this day up, up in the air for her. One possibility is doing PCC, Polynesian Culture Center or something over on the Windward side, maybe doing Homaluhia Botanical Garden. I don’t know, Wamanalo, but, uh, it’s gonna be up to her what she wants to do that day. So your Thursday will probably look completely different than mine.

[00:12:21] Bryan Murphy: Maybe you have a day like that, maybe you just, you have someone special that you’re celebrating and you just kinda hold it loose for them for that day. All right.

[00:12:28] Honolulu and Waikiki Day

[00:12:28] Bryan Murphy: So then Friday is our Honolulu and Waikiki Day. We’re gonna be starting off with Iolani Palace. This is something I really wanted to include because our girls are older and I want them to learn more about Hawaiian history and the Hawaiian kingdom.

[00:12:43] Bryan Murphy: So we’re planning on doing the self-led audio tour there. If you’re interested in visiting Iwolani Palace, it’s worth knowing that the palace requires advanced reservations for those audio tours. After that, I want to get everybody in agreement to go to Margarita’s Hoi for lunch. We’ll see how that goes.

[00:13:03] Bryan Murphy: But my buddies over there, they were also on the podcast. Man, been doing the podcast for almost nine years. Pretty cool to see how many, uh, local businesses we’ve, we’ve had on. But Margarita’s Hoyi is a special spot for us. Incredible drinks, really good food. We’ll see if everyone can get on board for that.

[00:13:21] Bryan Murphy: If not, find something in Waikiki, maybe do Dukes or something, touristy like that, which is cool. Do some shopping, nothing too structured after Yolani Palace. And the reason these activities work well is together because they’re in the Honolulu area. We’re not making separate trips from the west side into town for each of these.

[00:13:40] Last Resort Day and Departure

[00:13:40] Bryan Murphy: And then Saturday is our last full day, the saddest day of all. We’re gonna be just doing resort. That’s just what we like to do last day. Nothing major, anything like that, that’s too demanding of our time or, uh, energy. The girls will just, you know, enjoy the pool, the beach, lagoons, have breakfast in the villa, lunch.

[00:13:58] Bryan Murphy: We’ll do one last dinner at Monkey Pod. That’s what, three dinners at Monkey Pod, and then plus Allie and I, we’ll probably do a Monkeypod lunch. You’re like, “Man, you’re obsessed with Monkeypod. It’s our favorite restaurant and we’re in Southern California. We don’t have a Monkeypod.” So kinda like when in Rome, kinda like when on Oahu, you go to Monkeypod.

[00:14:17] Bryan Murphy: So that’s just us. This is our itinerary. The last day, Sunday, we don’t do anything. We gotta get up, eat a quick breakfast, maybe just even do breakfast on the go, Starbucks or something like that. We head out.

[00:14:30] What We Skipped and Why

[00:14:30] Bryan Murphy: Now, here’s the part I think is just as important as everything else. There are several other places I wanted to go.

[00:14:36] Bryan Murphy: Manila Falls, that was originally on our list and Homa Luhia Botanical Garden was on my list. If our birthday girl wants to go there, we’ll do that. Also, we considered Kulua Ranch, Bishop Museum, c – and a point. Not sure if we will be doing any of those. I, I don’t think we will on this trip. They’re all worthwhile experiences, but the more I worked through the itinerary and though about it, the more I realized we were still getting away from the kind of trip that we wanted.

[00:15:04] Three Itinerary Rules

[00:15:04] Bryan Murphy: So if you’re working on your own Oahu itinerary, there are three things I encourage you to do. First, give each day one main activity. You can add a few smaller things around it, but don’t feel like you need to schedule every single hour. That across the island traveling adds up real quick so you don’t wanna be watching the clock and getting worried.

[00:15:25] Bryan Murphy: Just keep one main activity, one anchor activity a day. Second, group your activities by location. Look at where things are before you start assigning them to different days. That’s how I ended up with one North Shore day and one Honolulu day. And number three, protect your downtime like it’s sacred. If you’re staying somewhere because you love the resort, make sure you actually have time for the resort and you actually have time to enjoy it.

[00:15:50] Bryan Murphy: And that goes for any island, not just O’ahu. You paid all this money to have this experience. Really enjoy it and be okay to say no to maybe something on the list. That’s really how I ended up with our itinerary because we always started with so much more than what we can actually do. And one, like, just side note, if you have older kids, get their input.

[00:16:16] Bryan Murphy: You know, that’s something that I always ask our girls, like, “What do you wanna do? Like, what’s your one thing?” Because that’s just gonna make it all the more better. Give everyone something to look forward to and not just sit in the car like, “I’m bored because they didn’t pick that activity,” or whatever the case may be.

[00:16:31] Free Planner and Wrap Up

[00:16:31] Bryan Murphy: Now, if you wanna see how everything fits together, I’ve put together a free seven-day O’ahu itinerary planner. It includes our actual family itinerary, plus two other examples. One for first time visitors and another for people who want a more relaxed vacation. There’s also a blank planner so you can build your own week based on these strategies that I’ve taught over this episode and over the last episode, 264.

[00:16:56] Bryan Murphy: And I, I love to hear what you think. What are, what are you planning? If you’re heading to Oahu, what’s one activity you’re trying to decide whether to include or not to include? Maybe you’re choosing between two different experiences or you’re just not sure how much you can fit into one day. Send me a DM, send me a message on Instagram at hawaiis.best.

[00:17:16] Bryan Murphy: I love to hear from you what you’re working through. Any way I can just help be a second set of eyes on your itinerary. And coming up this Thursday, I’m talking with Jennifer Santos from Honolulu’s Mayor’s Office of Culture and Arts. And we’re discussing Vahipana, a project that’s helping share the Hawaiian stories connected to the places around Oahu.

[00:17:37] Bryan Murphy: Jennifer shares some really interesting things about Diamond Head, for example, Le Ahi, and why understanding the history of a place can change the way you experience it. So make sure you’re following the show on Apple Podcasts or on Spotify so you don’t miss the next one. And until then, as always, live with Aloha.