In February 2020, Kristen had the opportunity to attend a conference for continuing education in Oahu, HI. She had been to the conference in 2018 as well and really enjoyed the information, so we decided to go back this year. Last time it was just us (Kristen and Zak). However, this time we decided to have our daughter come with us, as well as Zak’s dad and stepmom. Our daughter had been talking about wanting to go to Hawaii since Zak and I last went two years ago. So, we decided we would make her dream come true and take her with this time.

Day 0 – Day before the flight

We had meticulously planned the itinerary the day before our flight because we would have to travel almost 4 hours to the airport.  About a month prior to vacation, we shopped around to find the best “Park, Sleep, and Fly” deal in Minneapolis. This deal allows someone to book a hotel near the airport, use the airport shuttle to get to and from the airport, all while your car is parked safely at the hotel for up to 7 days. 

Once we chose a hotel, we even called to confirm the number of days we were allowed to park. So we booked the room, and everything seemed fine. However, when we got there, we were told they only allow that specific deal to happen if you book through the ParkSleepFly.com page – which we were not told when we called and asked about this.  Nor was it listed on their website. This caused a massive issue because we were now 4 hours away from home, about to catch our flight early the next morning, and had nowhere to park our car for 7 days.

Luckily, the lady at the desk was incredibly helpful.  She gave us all of the options we had at that point, and even offered to fully refund our pre-paid room, should it come to that.  We looked online and the ParkSleepFly site did not have any rooms available at that hotel, so we opted to just cancel our reservation, reserve a spot at a Park and Fly lot, where you drop your car off, and they shuttle you to and from the airport.  We also decided to stay at my father’s house the night prior, and just load all of our stuff in the vehicle the next morning, and head to the parking lot.

This just goes to show you that all the meticulous planning in the world won’t prepare you for random things that pop – but your ability to be flexible will.  With the help of generous people and great customer service, we dodged a major bullet. Always forward, never back.

Day 1 – The Flight

Usually when we fly, we fly Southwest.  They’re much more laid back than most airlines, and they actually make traveling with kids very simple.  However, we got a great deal on Delta, so we decided to go with them. We had previously flown with Delta and had a good experience, but we can’t say the same for this trip.

Apparently, with Delta, economy seats are the middle seat in every row.  This means that 5 of us would be sitting in the middle seats in a string of rows – and not together. We told the Delta worker at the gate desk that at least two of the seats had to be together because we had a 4 year old with us. When we pointed this out, we got a bit of a rude lecture about economy seating, and she briefly said that our 4 year old would have to sit in a middle seat by herself. (Umm..yea, because strangers sitting next to her are going to take care of our 4 year old while she’s screaming for us on the flight? Right…) After pointing this out, she very begrudgingly gave us two seats next to each other.

She claimed that all economy seats are in the middle and that we should have known that (even though it did not specify that during booking) and next time we need to pay extra if we want seats next to each other. We have never booked anything besides economy when flying (on Delta and other airlines) and have always had seats next to each other. Also, on our next 3 flights to and from Hawaii, our entire group of 5 people was sitting next to each other, and we didn’t even have assigned seats until we got to the gate. I’m not sure why that first woman was so bent out of shape, but it really turned us off of the idea of using Delta in the near future, even though they were one of our favorite airlines to travel with.

The first flight went reasonably well.  However, as we got closer to LAX, the flight became increasingly more turbulent.  When we went to land, I felt certain we were going to crash. The wind was so strong that, even after we had a less than smooth landing and the plane was “attached” to the terminal, the plane still was shaking due to the wind.  The second flight was so turbulent that the Captain postponed in flight service because it wasn’t safe for the attendants to walk in the aisles. However, that landing was much smoother than the first one.

Day 2 – Wiliwilinui Ridge Hike

Oahu has some amazing hiking trails, so we knew we wanted to do some hiking while we were there. The last time we went we did the Lanikai Pillbox hike, which was a little challenge, but short and manageable. Kristen wanted to do a ridge hike this time, so we decided to do the Wiliwilinui Ridge Hike.

Whoever said this hike was “intermediate” are out of their minds. People say this is the “easiest ridge hike” in Oahu, but if this one is the easiest, we’d hate to see what the other ones are like. There was nothing easy about this hike. The first 3/4ths of hike seems normal. Lots of hills/inclines, but overall a normal-like trail.  But then you get to what are known as the “stairs.”

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I want to clarify up front that these are not actually “stairs.”  They’re slats of metal and wood placed in a stair-like configuration on the path to help prevent erosion.  They’re not evenly spaced apart, and they’re placed at random heights, anywhere between 6 inches to 3 feet high.  In some instances, other hikers have placed rope to assist in the more steep stair sections.

After the first section of stairs, you’ll come across a random sign that tells you that the “stairs” from there on forward are not that safe, and that you need to be even more careful.  This is probably because there is a thousand foot drop-off on both sides. The stairs also become much more steep from that moment forward.

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With all that said, the views are stunning. Probably the best on the island – and you don’t even have to make it to the very top to see them.  Even if you only make it up the first section of stairs, you’ll be greeted with amazing views. Our pictures don’t do the views justice at all.

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We are so incredibly proud of ourselves for doing this hike! It was a challenge for us as it was probably the most difficult hike we have done, but it was so worth it! It took us about 4 hours round trip. We stopped frequently to take in the beautiful views. Thankfully, the weather was perfect for hiking – not too hot and not too cool. I’m glad we did it in the morning as I think it would have been much warmer in the afternoon.

This hike will test you physically.  If you’re afraid of heights, it will test you mentally. If you attempt it, make sure to take a ton of breaks, bring/drink lots of water, and take a bunch of snacks.

Day 3 – Snorkeling and Shopping

In the morning, we went snorkeling at the Turtle Bay Resort on the North Shore, while Kristen was at her conference.  As all beaches are public property, the resort is required to provide public beach access parking. Granted, at the resort, this is at the very back of the parking lot, which means you’ll have the pleasure of walking a fair distance to the beach, but it’s worth it.

The bay itself is protected by a rock outcropping that breaks the waves prior to them hitting the bay.  This means the waves in the bay are subtle and great for snorkeling. When we snorkeled two years ago, the reef itself was dead and there weren’t many fish.  However, when we went this time, the reef seemed to be slowly regrowing, and there were a good amount of fish to see. Overall, Turtle Bay is a great place for beginner snorkelers, and I highly recommend it.

Up the east side of the island, along Kamehameha Hwy, past the Polynesian Cultural Center, there are plenty of places to stop and shop.  If you keep going, you’ll come across a bazaar with tons of knick-knacks and food trucks. This is where the famous Giovanni’s Shrimp Truck is located, however many of the food trucks there have good food.

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Just past the food trucks is a place called Seven Brothers. If you are ever in Oahu, it is a must that you eat at Seven Brothers! We would recommend trying their burgers and fries. The fries are out-of-this-world delicious! But honestly, you probably can’t go wrong with anything you order from there!

Another shop that we stopped at along the highway was Ohana Island Creations. This is a family owned store that makes wood carvings and sculptures. They have some of the most amazing wood carvings we have ever seen! We will let the pictures below do the talking…

That evening, we enjoyed a dinner reception that was put on by Kristen’s conference. The conference-goers and their guests enjoyed a family-oriented meal. They had prizes for both kids and adults. The kids were invited up and were asked questions. If they got a question right, they got a prize. Our daughter got a question right, so she got to pick out a prize. Of course, she picked out the largest prize they had…a bucket full of sand toys. Our first thought was, “how are we going to get that packed into our luggage for the plane ride back?!” (Spoiler alert: thanks to Zak’s amazing packing skills, we got every last piece of it packed)!

Day 4 – Kualoa Ranch – Rain and UTV tour

When it rains here, it rains. (I guess that’s what we get for going during the rainy season). It rained so hard here our fourth day that the streets were flooding and some places were closed, but not Kualoa Ranch.

At Kualoa Ranch, they do tours rain or shine.  We had booked a “UTV” tour online with them. A UTV is like a gator or other 4 door recreational vehicle. You get to drive this vehicle around the ranch on a tour, led by someone on a 4- wheeler. This was an amazing experience! While the rain put a little damper on seeing the sites, the UTV tour was actually more fun in the rain! We got to splash through potholes and flooded creeks along the trail. Check out a short video of our tour HERE. They gave us ponchos to help keep us dry. We also dressed warmly because the temps were in the mid-60’s, which is cool for Hawaii. The tour guide said it’s actually some of the coldest weather he’s experienced in Hawaii.

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Along the tour, we were able to see beautiful views of the mountains with some natural waterfalls coming down them due to the heavy rains. The tour took us to movie sites, including those from Jurassic World, Mighty Joe Young, Fifty First Dates, Kong Skull Island, and others. We were the only crazy ones on the UTV tour in the rain, but the perk of that was our tour guide spent more time with us. He offered to take our picture and we even got to make our own movie clip! Click HERE to watch us get eaten by a dinosaur on our YouTube channel!

We highly recommend taking a tour at Kualoa Ranch if you ever find yourself on Oahu!

Day 5 – Scuba Diving, Waikiki Beach, Shopping, and Pearl Harbor

Thankfully, day 5 of our trip ended up being sunny and beautiful! Kristen didn’t have her conference that morning, but our day still started really early. Zak was scuba diving that morning and had to be at the marina in Honolulu by 7:30 am. Since we were staying at Courtyard by Marriott on the North Shore, that meant we would have a very time consuming drive to Honolulu in rush hour traffic. We left the hotel at about 5:20 am and arrived at the dive boat in Honolulu just after 7. (If you don’t have to drive in Honolulu during rush hour, don’t. Avoid it at all costs because it will take you hours).

After we dropped Zak off, I decided I wanted to spend some time at the beach. I hadn’t made it to the famous Waikiki beach during our last visit, so I decided to take my daughter there while Zak was on his dive. It was only about 10-15 minutes from where we dropped him off. Zak’s dad and his stepmom wanted to do some shopping, so they dropped my daughter and I off. It was kind of nice that we were able to each do our own thing for awhile.

We got to the beach at about 7:30 am, lugging along my backpack and her large bucket of sand toys. As we stepped onto the beach, we looked to the left and could see light from the sunrise peeking from behind Diamond Head. There were a few groups of surfers out on the early morning waves and only a few people walking or sitting along the beach. The beach was quiet and all we could hear were the waves and seagulls. It was a peaceful beginning to the day. I spread out a beach towel for us to sit on and we got busy playing in the sand.

When it started warming up, we found a bathroom outside at one of the hotels to change into our swimsuits and grabbed some snacks from their snack bar. As the morning progressed, the beach became very busy and catamarans pulled up onto the beach advertising tours. I found this slightly annoying because it blocked the beautiful view of the ocean and they made people move from their spots on the beach so they could tie the boats up. Not as relaxing as Carolina Beach was. Nevertheless, we had an enjoyable mother-daughter morning at the beach.

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After Zak was done diving, he and the others picked us up from the beach and we went to the Pearl Harbor Arizona Memorial that afternoon. (Thankfully, we made it to the correct place this time, as on our last trip our GPS took us to the Pearl Harbor Naval Base instead of the memorial…Kristen may or may not have been in charge of directions last time).

Visiting Pearl Harbor left us feeling solemn. We knew the story of Pearl Harbor, but to be standing there where it happened was very moving. The USS Arizona memorial tour starts off with a movie describing the history of the Pearl Harbor attack, followed by a boat ride out to the memorial site. Standing in the room of the memorial that had everyone’s names who had lost their lives in the attack that day was chilling. The room was silent. As people stood there reading the names, many of us had tears in our eyes.

After Pearl Harbor, we headed back to our hotel. Zak and I hadn’t been to Kahana Beach yet (which on our last visit there we deemed “our beach”). So, we decided to head down the road to that beach while our in-laws stayed at the hotel.

Kahana Beach is along Kamehameha Hwy. It has never been busy when we have been there. There’s usually only a few others walking along the beach. It is along a large bay surrounded by mountains on each side. It was sunset by time we got there, so too cold to swim, but we took off our shoes and walked through the water and enjoyed watching our daughter have fun. There was another woman walking with her two dogs along the beach and another family with a 3-4 year old on a toddler sized electric-bike (super cute) zooming up and down the back side of the beach.

On our way back, just a few minutes north of Kahana beach, we stopped at another side-of-the -road beach. This beach had a couple swings hanging from a tree. We let our daughter swing for a little while. The swings overlooked the beach which was partially lit by the last of the sunset and partially by the full moon glimmering on the ocean. It was a perfect last evening in Hawaii for us as a family.

Day 6 – Conference, bazaar, Dole Plantation, and flight back

Saturday was our last day in Oahu. Kristen attended her conference that morning while Zak and the rest of the family spent the morning packing and checking out of the hotel.

The conference ended at about 1 pm and we stopped at our favorite bizarre for some lunch at the food trucks. Kristen went to a chinese food truck (as she doesn’t like seafood) while the rest of us ate at Giovanni’s.

After that, we headed along the North Shore and back down south a little to the Dole Plantation. The waves along the North Shore that day were the biggest we had ever seen. There was a “no swimming or surfing” warning at all the beaches. This video doesn’t do it much justice, but shows how rough the waves were that day. We even witnessed a helicopter hovering over the ocean along one of the beaches searching for a person in the water.

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The Dole Plantation was a bright and colorful place. I learned a lot about pineapples (for example, did you know that pineapples grow in the ground? I always thought they grew on trees)! They have many other things they grow there as well including other fruits, bananas, and cacao (aka what chocolate is made from). While the wind that day made it slightly cool, it was a sunny day, which made for a beautiful tour of the plantation. We took the train ride around the plantation and then afterwards had a pineapple Dole whip.

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After leaving the Dole Plantation, we headed to the airport in Honolulu. Our flight left at 9:30 that night. Our daughter thankfully slept the entire flight back. Unfortunately, us parents didn’t get much sleep. Trying to get comfortable enough to sleep on a plane can be a challenge. Needless to say, it took us a few days to catch up on sleep.

Although we didn’t get to do everything we wanted, we had a good family trip to Oahu. Our daughter really enjoyed it and hopefully we made some great memories that she will remember forever. She was actually disappointed to leave saying she wished Hawaii could be our new home.

We really like Oahu, but the Honolulu traffic kind of puts a damper on the island. There are signs towards the North Shore in opposition of new development, and I have to agree with them. The island is so beautiful but is becoming too crowded. They should do what they can to preserve what beautiful land they have left. If we ever make it back to Hawaii, we would probably choose to visit a different island such as Maui or Kauai.

Have you ever been to Oahu? What was your favorite thing to do there? Leave a comment below! Mahalo!