Oahu Family Vacation Plan + What I Wore

Last week, we took our family of four (two adults and two tween boys) to Hawaii and stayed on the island of Oahu for six days and five nights. Here's a look at what we did each day, what I wore, where we stayed, and what activities we would recommend or not for other families in a similar stage who are planning a trip to Hawaii.
Day One:
Travel to Hawaii, get settled 

We flew via Alaska Airlines and were very pleased with the in flight service, food options and entertainment options. Our only other direct flight option from San Diego was Hawaiian airlines and my husband had a bad experience with them on a previous trip so it was an easy choice. I hardly ever mention the airline we used (although usually it's Southwest) because it's just a means to an end, but Alaska really made the flight more enjoyable so I thought it was worth a mention.

We stayed at The Laylow (a Marriott "Autograph Collection" property) on Waikiki Beach.
This is a brand new hotel (it opened in March of 2017) and we loved it. It was perfect for our needs. It was very clean and modern, and the staff was always friendly and helpful (even down to simple things like letting us use their clean pool towels to take off-property to the beach every day so we didn't have to bring or buy our own). Plus the concierge made a lot of great recommendations for our trip since we had very little planned when we arrived. The location was also excellent. We were one block from the beach and there were probably hundreds of restaurants and stores within a two block radius. We settled on this place largely because our room had two King Size beds (which is pretty rare in hotels!) and that made sleeping a lot more comfortable for our family. And that was the main thing we were planning to do in our room since this trip was all about being out and about!

Day Two:
Dole Plantation, North Shore, Polynesian Cultural Center

Day two was packed (actually over-packed, more on that below) with three main activities:

Dole Plantation:

Our first stop and first activity of the trip was a visit to the Dole Plantation.  I'm actually glad this was our first because while we enjoyed it well enough, in retrospect it seems weak compared to the other stuff we did! If we had done it last we might have been a little more bored. The plantation has a maze (like a corn maze except pineapple, of course) and a little train ride where you learn more about the history of pineapples and other crops in Hawaii, plus a retail shop and snack area. It was interesting and relatively enjoyable, but we didn't stay long. We also didn't have any of the pineapple ice cream or specialty treats they sell because none of us were really in the mood for it. Overall I would still recommend this as an good family activity, but maybe on a day where you just need something slower paced. I wouldn't really consider it a must-see. I've been to all kinds of apple farms, strawberry farms, pumpkin patches, etc. here in California and in the Seattle area and this is pretty much the same thing, just a different crop in different weather.

North Shore: 

Next we drove up to the North Shore to check out the famous waves, and they did not disappoint! We stopped at Waimea Bay Beach park to let the kids play in the water for awhile...under close supervision near the shore. They had a blast letting the waves crash over them without any boogie boards or anything else. After that we kept driving up around the North Shore to find lunch and Shaved Ice. We stopped at Shark's Cove at an area with a bunch of food trucks. The food was just okay and the service was mediocre to bad at some of the trucks. But it was enough to fill us so we could go on to our final stop of the day.

Polynesian Cultural Center:
(I shared a video of this tree climbing demo at the PCC on my Insta-Story that day!)

This is a great place to learn about the history and culture of Hawaii, Tahiti, Tonga, Samoa, Fiji and Aotearoa through live presentations in a very scenic "theme park." Most people go and spend the full day here, which would be easy to do if you want to see a presentation at each of the villages, plus take in the night show (the best part, in my opinion!) at 7:30. That said, my husband and I have both been here before and he wasn't keen on spending the whole day here again. So we got there around 4:00 and only went to the final Samoa and Tonga presentations (several people told us those were the best two so we made sure to see them), followed by dinner in the banquet hall and the night show. I enjoyed everything we saw an experienced, and so did my family. But the biggest mistake we made in planning our trip was doing this activity on the day after our arrival when we were still on California time. The night show started at 7:30, which was 10:30 to us, so it felt very late on top of being tired from a full day of touring and wave-surfing. The kids were practically asleep when the show started, but it did grab their attention and kept them awake until they could crash in the car. The night show is my absolute favorite (probably of the whole trip) just because you all know I really enjoy dancing and watching different styles of dance, and the night show is all about telling the story of Polynesia through dance.

Day Three:
Hike & Bike Tour
  Rainforest to Reef: Hike and Bike Tour

This was one of the activities the concierge recommended for our trip and it was awesome. Prior to this, the closest I have ever been to a rainforest is Rainforest Café and this was far more beautiful and incredible. Our guide picked us up in a van about a block from our hotel and took us up to a hidden trail where we did a two-mile hike rainforest hike up to a waterfall (I honestly can't remember the name our guide told us, it wasn't Manoa falls and he said it isn't on Google maps...). We saw all kinds of beautiful, lush scenery and views. We never would have found and navigated the trail without the guide, and he was incredibly knowledgeable about every plant and tree in the rainforest, not to mention every aspect of Hawaiian history and culture! He was also well-prepared for us with rain ponchos, mosquito repellent (we still got bit though), snacks, water etc. The trail itself was not difficult in terms of incline, but it was slippery and narrow in parts and took some careful footing. Our guide provided us with Trek sticks to help with balance, and many times I had to use that plus a bamboo branch to make my way on the trail.
 Views from the Rainforest

After we hiked the rainforest, we came back down the same trail to the van where we drove up to Puu Ualakaa Lookout.
View of Honolulu from Puu Ualakaa State Park (See Day Three)

We had lunch there (provided by the tour company) and then went up to the top of the hill to do our 5 mile downhill bike ride. It was a really fun way to enjoy the views of the island while sailing down the hill on a bike!

We returned from the tour in the late afternoon and the kids swam for awhile in the hotel pool, then we grabbed dinner and were done for the day!

Day Four:
Dolphin Watching and Snorkeling Cruise

For this tour package (which we also chose based on the recommendation of our concierge), a tour bus comes and picks people up at a few different hotels around downtown Honolulu before taking everyone out to the west side of the island to cruise around looking for dolphins and then snorkel. On the boat we were served muffins, coffee, sodas as we boarded, and later on they provided a full Hawaiian lunch and alcoholic beverages for those of age. It was a very full service experience. We cruised around in the boat a little until we found a pod of dolphins (or mega-pod according to the captain). They estimated about 200 dolphins so we really did see a lot of dolphins. There were a few dolphins who seemed to like racing our boat and stayed by our side for quite awhile. So for dolphin sighting in the wild: five out of five stars!

Next up we stopped the boat for the snorkeling portion of the day.

I don't snorkel (I just cannot get the hang of it) but my husband and kids did and they did see fish, but my husband felt it was nothing spectacular and not better than what you see at Haunama Bay. So for the snorkeling portion 3 out of 5 stars.

After snorkeling, they served lunch and drinks and just cruised around on the boat. (Again the food was maybe 3/5 stars. My kids would give it 1 out of 5 stars but they're picky eaters.) The sun was finally out for awhile at this point so it was nice to sit outside and enjoy the weather and scenery. When the boat took us back to shore, we got back on the bus for the ride back to Honolulu. We spent over an hour on the bus each way between island traffic and dropping everyone off at different locations in the city.

This tour is on my short list of "things I would do differently next time." When all was said and done, my kids enjoyed it and thought it was cool, so I'm glad for that. However, we were gone from 10:00 AM until about 6 PM, but out of an 8-hour day we only got a good 90 minutes of actual fun-time (30 minutes a piece of boat cruising, snorkeling, and dolphin watching). We spent almost three hours of the day just on the bus. We could have driven there ourselves in our rental car and saved a lot of time. The snorkeling wasn't so impressive or unique that it was worth the trouble of the bus and boat rides. I think a simple 1-2 hour dolphin sighting boat ride (minus bus service) would have been a better fit. (And in the bigger picture of scheduling, if we had done that one morning maybe we could have done the Polynesian Cultural Center in the afternoon/evening that day). The food, snorkeling, and bus ride just weren't worth the extra time and expense for us. I hate to say anything negative about the tour because the staff were all fun, friendly, and enjoyable. We signed up for it all knowing what it entailed and how many hours it would be, so that's on us. It wasn't a bad experience, it's probably just different stroke/different folks. I would also add that this happened to be the day of our trip with the worst weather: lots of clouds and intermittent showers. There was some sun here and there but more clouds than sun. So that meant we spent more time uncomfortably packed in the boat rather than out on the deck, which is no one's fault but took away from the experience all the same.

Day Five:
More Beaches and Snorkeling

This was our last full day on the island and we let the kids choose the activity. They wanted to get back in the water, so we decided to go to Haunama Bay. We pulled up around 9 AM...and the lot was full. They told us to check back every 30 minutes to see if we could get in. Waiting around and checking back every 30 minutes didn't seem like the best use of our time, so instead we googled nearby top-rated beach options and decided to head to Kailua Beach Park:

The scenery was beautiful, it was relatively quiet, and there were lots of trees with shade where we could hang out and easily watch the kids in the water, so that was nice. And since the water was very calm it wasn't as stressful as the North Shore. It would be a great place for families with younger kids. That said, mine were done here in an hour because they like a little more action. We decided to go back to Haunama Bay to see if we could get in yet, and luckily we did!

I'm so glad we went back and were able to get in here. It was truly beautiful and the kids had a great time snorkeling. We had heard from several locals and Hawaii-regulars that it was overrated, the snorkeling wasn't that great, etc. But we decided to go anyway and it was completely worth it for us.

Day Six:
Waikiki Beach and Travel Home

We didn't have to leave our hotel for the airport until 2:00 in the afternoon, so we decided to get in a little more beach time before packing up to head home. We decided to stick close to the hotel and just go to Waikiki Beach.
My boogie board crew on Waikiki Beach 

Is this beach touristy and busy? Sure, but it was convenient, very nice and enjoyable. We we went through the lobby of the Outrigger Waikiki (my sister is a Hawaii-regular and that's her favorite hotel), and it was great because we were able to rent two beach chairs, an umbrella and three boogie boards for $60 which made for a fun, comfortable beach experience and a nice way to spend our last morning.

After that we grabbed a quick bite at a nearby restaurant and then it was time to pack-up, clean-up, and go home!

What I Wore:
As you can gather from my activity list, I needed a lot of functional, comfortable outfits for this trip. I wasn't on a blogger-trip to showcase cute outfits in beautiful scenery, so I really tried to keep it very simple. I wouldn't even bother posting these outfits to the blog, other than hoping they serve as somewhat visuals for anyone packing for a similar beach/outdoorsy/family-friendly trip.

ONE: (Worn for airport travel both ways)
Shirt: Express (Similar) | Tank: Target | Shoes: Amazon | Bag: c/o Amazon | Leggings: Express

TWO: (Worn to Dole Plantation, Polynesian Cultural Center)
Tank: Target | Shorts: Nordstrom Rack (Similar) | Shoes: Sam Edelman | Bag: Fossil

THREE: (Worn for Dolphin/Snorkel Boat Day)
Swim Cover Up: c/o Amazon | Flip Flops: Target

FOUR: (Worn for Rainforest to Reef Hike & Bike)
Tank: Gap (Current) | Shorts: Target (Similar) | Sneakers: New Balance (Similar with more sizes)

FIVE: (Worn to hotel pool, sorry I was too lazy to iron this on vacation)
Swim Cover Up: c/o Amazon | Flip Flops: Target

SIX: (Worn out to dinner two nights. It was too dark to photograph this in real-time, but I was very glad I packed so I re-did the outfit picture at home to share.)
Dress: Express | Necklace: Kendra Scott | Bag: Fossil | Shoes: Vince Camuto (Similar)

* * *
This is quite possibly my longest post of all time, and that's saying something since I can be pretty wordy! I considered breaking it into two posts, but generally I find it easier for myself to locate past posts when the topics are consolidated like this so I decided to just go for it all in one spot today. To be clear, no portion of this trip was sponsored or compensated by any of the brands mentioned. This trip was entirely sponsored by my husband and his full-time day job! But if any travel brands would like to sponsor our next trip, by all means hit me up! 

Have a great weekend and see you back on Monday!

Linking up with:



  1. Love hearing about the things to do on Oahu. I've been to Maui a few times but none of the other islands. The beaches look amazing and the dolphin watching would be so fun!

    Doused In Pink

    1. Maui is next on our list for a "big" vacation. I will have to hit you up for suggestions of what to do there when we go!!

  2. Oahu is so much fun! I've been twice, and both times had different experiences because there is so much to see and do! I'm glad you all enjoyed it! Maui is still my favorite but mainly because my godfather lives there and I know the island extremely well. It's definitely a slower pace and very laid back in comparison to Oahu. Some people find it boring which I take offense to lol! I almost moved there after high school and still dream about it!

  3. I am saving this post. I've never been to Hawaii and it is at the top of my list to do. My husband wants the kids to be just a bit older to enjoy what it has to offer. It sounds like you had a great time and thanks for putting so much effort into this post to share your experience.

  4. it sounds like you packed a lot into that week, and i would love to go back to hawaii. maui is my favorite island..but i've only been there and kauai. i think you will all love maui whenever you decide to go! from philly it's so stinking far...i could get to europe faster! there's just something so special about hawaii, right?!? i would love to snorkel in hanauma bay b/c of it looking protected.

  5. I went to Hawaii as a child and remember the Polynesian Cultural Center and Dole Plantation! They were both fun activities! It sounds like you had a wonderful time!

  6. Well I am adding Oahu to my bucket list! :) It looks absolutely gorgeous!

  7. You, Rachelle, and Noelle have all been to Hawaii now since I've known you and I'm definitely feeling like I am missing out!! It looks gorgeous! And I know how time consuming this post must have been!!! It will be a great reference for me later!
    Carylee | http://morepiecesofme.com

  8. Wow you covered a lot of places on your trip my fav is the white beach cover up

  9. Sounds like you had a pretty packed vacation! When we travel, we always try to find 2 queen beds so that it's more comfortable for everyone. 2 kings is a rarity!

    I grew up on Oahu and have never gone to PCC but have dropped off many friends there when they visit. I think next time, I will take my son there, I think he would enjoy the show.

    IG: @happinessatmidlife.com

  10. i've heard good things about Alaska Airlines but never had a reason to use them (or destination rather). we mostly fly southwest as well, if southwest doesn't go there we probably won't either. ha. i wish they flew to Australia!
    the dolphin cruise sounds so fun! we are doing a whale watching/dolphin cruise in NZ and I can.not.wait! i hope we see all the things.
    i went to hawaii in 2011 and i would love to go back. i went with my mum and we really didn't do a lot (i wasn't a good planner/researcher then!).
    ps. i always prefer longer posts if it means everything is in one post. i prefer to write them that way and i prefer to read them that way. vacations, researching other stuff, whatever it is, if it's in more than post i won't read it lol.

  11. Oh I'm so glad I found your post through Momfessional's travel link up today! I live on the North Shore of Oahu and so I always love reading about when people visit and what their high/low points of their trip are. Hanauma Bay is good, but you're right - so crowded. If you come again, definitely try Dole Whip at the Dole Plantation :)


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