All About Our Family Trip to Hawaii

Two weeks ago we went to Hawaii with our family. Here are all the details and answers to your questions about our trip!

A Q&A all about our Hawaii trip

When we returned home from our trip to Hawaii, I asked over on Instagram what questions you had. These were the most commonly asked questions, and my answers all about our Hawaii trip!

Q: What island did you visit?

• We stayed on the island of Oahu.

Q: What hotel did you stay in?

• We stayed at the Hilton Hawaiian Village. Honestly it’s the most family friendly resort on the island. It has lots of restaurants, activities and different pools, plus gorgeous views and it sits right on the beach! The man made Lagoon (seen here) was my kids’ favorite with lots of water toys to rent, a little island to float around, and calm water surrounded by sand so you don’t have to worry about little kids by the water but still get the beach feel. Also there are tiny fish in the water!
• The other two pools had water slides, a shallow pool for little kids, and restaurants right by the pool so you could eat lunch right there. Our favorite was the Wiki Wiki Market — seriously, try the croissant sandwich! It was right by the pool and better prices (and more kid friendly) than the poolside menu.
• We took a lei making class one day, my nieces did a hula dancing class, and there were plenty of other fun activities provided by the hotel that we didn’t have time to do.
• Highly recommend this as a great family friendly hotel!

Q: How many rooms did you have to get for your family?

• This was a family reunion with Philip’s family, so we had 15 of us between our family, Philip’s sister’s family, and Philip’s dad.
• We had four rooms between us:
  • 1 room for Philip, Sanny and me
  • 1 room for Grandpa and my two older boys
  • 2 rooms for my sister in law, her husband, and their 5 kids

Q: What were the COVID testing/vaccine protocols?

• All of the requirements are outline HERE. They’re changing regularly, and they’re very in depth, so make sure you follow everything on here to a T and you’ll be fine.

Q: What did you wear?

• You can find everything I wore in Hawaii linked in this post.

Q: Did your hotel have a kitchen or did you have to eat out every meal?

• The hotel did not have kitchens, but it did have a mini fridge so we bought a few things at the store for easy and inexpensive breakfasts so we didn’t have to eat out for every meal. We ate the rest of the meals out or ordered to our hotel through Door Dash.

Q: Where were the best places you ate? Did you have to make reservations everywhere? 

• The bummer thing about restaurants was that most of them didn’t take reservations  for a party of our size, and/or they were at low capacity so it was really hard to get in. This is why we ended up Door Dashing most of the time, which worked fine, but wasn’t ideal when there weren’t a ton of places for 15 people to sit and eat.
• But by far the best meal we had was at Roy’s. We did a kid free date (leaving the kids with the rest of the family) and ate at this restaurant. The vibe was modern and cool, and the food was out of this world. If you ever go, absolutely get the pineapple upside down cake and the chocolate molten cake. They were insane.
• We also went to Fresco Italian Restaurant right on the Hilton Hawaiian Village property one day and it was super good.
• We never eat at chain restaurants when we travel. We love trying local food, finding holes in the wall, and eating at famous local joints. It was a little trickier with a large group and COVID limiting capacity, but we did have some good food.
• Also, you must have the Hawaiian canned juices when you’re there! POG is our favorite.

Q: How did you get your kids adjusted to the time change?

• We lost five hours on our way, so we arrived at 4pm in Hawaii when it was 9pm at home. My boys are great sleepers and we just kept them up til regular bedtime, and then used black out shades and white noise machines so they slept in til a fairly normal time. They almost instantly adjusted!

Q: What was your favorite thing you did?

• That’s a tough one! We did lots of fun things. Here are a few things we really loved:

1. Renting beach toys at the lagoon. They were crazy expensive, but literally worth every penny for the fun!
2. Hiking Diamondhead. The hike is pretty quick and easy enough for kids, and the views were stunning.
3. Dole Pineapple Plantation. Delicious food, fun maze, and a fun train that was very packed so we didn’t ride.
4. Polynesian Cultural Center. This is pricey, but it’s such a fun experience to learn about the cultures and tradition of the Pacific Islands. The people who work there are incredibly talented and so full of life. It was so fun to watch them perform and share and entertain. The night show was by far the best part — the luau was fun, but the food was “meh.”
5. Snorkeling and looking for turtles at the beach (snorkel gear was limited at the hotel, so we bought two snorkel masks at a local store and passed those around).
6. Actually, probably my favorite thing we did was swap date days with my sister in law. She took our kids for the afternoon/evening one day, and we took her kids for an afternoon/evening another day. She and her husband went parasailing and went to dinner for their day date, and we went on an afternoon run, got a couples massage, and went to a nice dinner at Roy’s.

Q: Something you wish you had packed/Favorite Thing You Packed?

• The one thing I forgot was my running belt bag — ugh! I had to hold my phone on every beach run that we did…that annoys me so much.
• My favorite thing I packed was THIS SEASHELL DRESS. I wore it for our date night without kids, and it was perfect. (I’m wearing a size 8 in their sizing and usually a size 2 in dresses).

Q: How did you entertain your kids on the flight?

• We flew on American Airlines and there are built in TVs, so the boys watched movies and played games pretty much the whole way there. Sanny’s eyes were bright red when we arrived, after staring at a screen for probably six hours straight, but he was happy the whole flight!
• We flew home on the red eye flight, so we all slept most of that flight.
• For every trip we take, we always pack a backpack for each kid with headphones, a ziplock bag of snacks, a book or two, an activity book or two, and a blanket. It’s honestly all they need!
• If you don’t have TVs on the back of your seats in your plane, make sure you’ve downloaded some apps that don’t require wifi — I have a big list here!

Q: How did you deal with rental cars? I’ve heard horror stories!

• So many people asked about this! Apparently cars were being rented for $500/day and people were resorting to renting U-Hauls because they have a fixed rate. Yikes!
• We did rent two rental cars….but my husband works for a rental car company, so we got his normal discounted rate. The employees behind the counter about choked when they saw his super low daily rate compared to all the other current rates.
• We only rented the cars for 24 hours so we could go to North Shore and to church on Sunday. Besides that, we did taxis, and there were plenty of taxis and their rates were normal!

Q: Was it super crowded? 

• I was actually shocked at how crowded it was. They had just removed the outdoor mask mandate, so I’m sure that had something to do with it.
• According to an article I read, they’re accepting vaccine passports starting this month, and also Southwest is opening 27 new routes to Hawaii. So if it was crowded then, it’s going to be reaaaally crowded soon.

Q: Do you have a strict budget going on big trips like this?

• We have never set strict budgets for trips. Every family is different, and you absolutely have to do what’s best for you and your family. But Philip and I have traveled since the moment we got married, and we’ve always had the mentality that penny pinching on vacation ruins it for us. If we can’t afford to go somewhere, we just won’t go. We don’t want to spend all our vacation time stressing about budgets and eating the cheapest meal or wondering if we can afford this or that activity.
• We have never gone into debt for anything, and most definitely not travel. We just both work really hard and save our money wisely so that when we decide to go on a big vacation like this, we can go and enjoy it and not even think about the money aspect. And don’t get me wrong, we don’t go crazy and splurge on anything and everything while we’re on vacation…we’re still mindful of how much things cost, but we don’t set a budget and if there’s an activity or souvenier or experience we want while we’re there, we know that we have money to do it without any stress.
• Also, we often use credit card points for plane flights (that’s what we did for our Hawaii flights), and we use Hotels.com and Hyatt Rewards for many of our hotel stays where we earn free nights or discounts, and we definitely take advantage of those. We try to be really smart about the big purchases so we don’t have to worry about any of the smaller purchases.

Q: How was the mask situation in public places?

• Hawaii had just removed the outdoor mask mandate two weeks before we arrived. Previous to that, masks were even required on the beach.
• So no one was wearing masks outdoors at all, but masks were still required indoors whether you were vaccinated or not. There wasn’t anyone enforcing around our hotel, but most people were respectful of the rules there.
• As far as the other public places we went, the mask requirements varied from place to place. The were not required at the Polynesian Cultural Center, but they were required at the Dole Pineapple Plantation. They weren’t required at our Diamondhead hike, but they were required in all restaurants when you entered.
• Again, things are constantly changing, so the rules may be different even now, two weeks after our trip.

Q: Best kid-friendly activities?

• Besides playing at the beach and the pool…
  • The Dole Pineapple Plantation
  • Polynesian Cultural Center
  • Hiking Diamondhead Crater
• I’m sure there are plenty more, but these were the ones we did. The only other time we’ve come to Oahu was without kids.

Q: How did you balance activities vs. down time at the hotel/beach?

• Philip made a full itinerary in the weeks before we left. He always does this on trips so we can plan and reserve things in advance as needed, and also make sure we fit in the things we want to do.
• Our itineraries are always overplanned, but very flexible. Just so we always have some kind of plan, whether we stick to it or not. I hate being on vacation and not having a plan (I want a plan, even if the plan is to sit at the pool all day).
• Especially when we were traveling with 15 people, there were a lot of varying opinions and ideas, so planning things out in advance is super important. We had everyone share specific things they wanted to do, and we made sure those went on the itinerary first, and then we built in the downtime around that.
• The most important thing with this trip, and all our other family trips, is to just spend time as a family. It honestly doesn’t matter what we do – it’s just amazing to be off of work, in a fun place, exploring, eating the local food, relaxing, and beith with each other.

There are a few more specific questions I got in the question box that I’ll be answering over on Instagram today, so hop over there if you have other questions that weren’t answered here.

I hope this was helpful! If you have other questions beyond these, leave a comment.

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