Hawaii Vacation as a family of 8

I want to share all the details of our Hawaii trip with you all! How we packed, what we did while we were there, what we ate, our favorite things we brought, and more. Buckle up for all the things!

Let’s start with packing:

We had 7 carry-on suitcases total. These are our absolute favorites. The 4 older boys had their own. Crew and Beck shared, Griffy and I shared, and Tim had his own. In their suitcase we packed their clothes in these travel cubes. Since we had a washer and dryer I was able to pack less. In each suitcase we also packed extra things we needed such as diapers, wipes, pullups, swim diapers, goggles, one pool floatie and some life vests so we didn’t have to pay for those in Hawaii. 

We only checked one bigger bag with things like Griffy’s portable bed (link here), accessories we planned to use with our Veer gear around Hawaii and a few other random items. 

The older boys each had a backpack with:

Headphones

The ultimate snack bag (Individually packed snacks such as applesauce pouches, crackers, fruit snacks, Clif bars, Chomps beef sticks etc.)

A book (I suggest a book that can keep them occupied longer)

A fire tablet to share

iPad to share

2 Gameboys to share (preloaded with 400 games)

Portable CD Player to share

Beck had his own personal backpack as well with his loveys, a snack bag and a few books. In hindsight I wish I would’ve bought him a pair of headphones too for listening to music or stories or watching a show on the plane. 

Instead of a stroller, we brought our Veergear wagon with the car seat attachment and it was the best choice- highly recommend. After owning multiple single and double strollers, the Veer took the cake for all around best use, ability to carry multiple kids (3 easily- baby/2 yr old/4 yr old), ease of use and most compact accessories that actually came in handy (like the pop up tent for the beach). We had so many people asking about it.

My flight tips: 

Buy or bring an empty water bottle to fill and have on the plane.

Feed your kids a half hour before boarding. We would split 2-3 bigger meals between 7 of us and that worked well and saved a little money.

Board first when they allow parents traveling with kids to board. Allows for easier settling in without feeling like you are holding the line up.

Don’t be afraid to let kids switch around seats every so often with each other. 

Take advantage of inflight movies if available! There were lots of movies we approved of for our kids that were free. And we are pretty picky on them.

Where we stayed:

In Kauai we stayed at Koloa Landing Resort. We stayed in a 3 bedroom villa, but they offer standard rooms all the way up to the 3 bedroom villa. It had a full kitchen and living room plus a large lanai. This gave us plenty of space to spread out and relax. Their pools are incredible with some having waterfalls, a medium and small waterslide for kids, mini splash pad and hot tubs all around that keep kids occupied all day. But the ocean is also right across the street and the nearest best beach is just an 8 minute walk down the road. You can drive there in 2 minutes. 

We also love that you can rent beach chairs, boogie boards and more for a really inexpensive fee and just charge it to the room. There is an onsite restaurant which has good food at decent prices ($20/entrée, $14 for a kids meal).

We did splurge and rent a cabana for 2 separate days ($150/day) and with little kids we found it to be extremely worth it. Especially with a baby. You get it from 9am-6pm that day. There are comfortable chairs and a loveseat plus a minifridge and a tv if your kiddos need a break from all the swimming. It was really nice since rain often comes in and out for about 5 minutes at a time, we could get out of the rain until the sun appeared again. The cabanas also have a fan. 

The resort does do poolside food and drinks and will come to you wherever you are around the pool to take orders. This is an extra charge you can pay for or charge to your room. 

Let’s talk food!

Restaurants we recommend: 

The Eating house- in Poipu, higher price ($40/entrée), fancier, delicious, great atmosphere

Keokis Paradise- in Poipu, great food, moderate price ($25/entrée), delicious, best atmosphere on the island in my opinion

Bubba’s Burgers- In Poipu, affordable ($4-8), easy quick food, great burgers

Porkys Kauai- a MUST for lunch in Waimea. 4 options plus kids options and affordable ($12/lunch)

Tidepools- Restaurant inside the Grand Hyatt in Poipu. Very fancy and expensive but very delicious and it sits over pools of koi fish. Really fun if looking for an extra special meal. 

Holoholo grill (restaurant at Koloa landing)- good food, good prices, easy when at the resort

Anakes- Sits in the back of an old grocery store, amazing acai bowls and smoothies

Da Crack- local fave for Mexican food. A bit over priced but yummy. Kind of like a chipotle style place. 

Chicken in a barrel- Several on the island. Delicious food for a decent price. Meat is incredible.

Jojo’s Shave ice- Best on the island. Has a couple locations

Waikomo shave ice- “natural” shave ice flavors. Good but not as good as Jojo’s. They are different though. 

Lappert’s ice cream- Try the lilikoi sorbet and you won’t be disappointed. 

Now to the Activities:

Kiahuna Beach (south shore) great for kids playing in waves, not rocky

Poipu Beach (south shore) great for little kids, snorkeling and lots of room but tends to be more packed.

Tunnels beach (very tip of north shore) very remote, larger waves, beautiful sandy beach. Probably pretty big waves for kids. Great for surfers. 

Snorkel Tour with Capt Andys- Tim, my dad and Jude and Hudson did this and said it was unreal amazing. Would highly recommend and they said the customer service and experience was over the top. 

Waimea Canyon- a must see. Multiple lookouts. Keep going beyond the main lookout. Do the lookouts at mile marker 10, 13.5, 18 (this was my favorite and just stunning) and 19. Road ends there and you turn around and head back the same way. Lots of other little stops and mini lookouts on the way up. Just pull off where other cars are pulling off. 

Hanalei Bay (north shore)- famous for its backdrop of mountains. Really beautiful and great for a beach day. Fun pier.

I hope you enjoyed reading all about our trip. Comment below if you have any questions that you didn’t see answers to here and I’ll do my best to share. We had fun sharing, and maybe you found a tip or two that would help in your next vacation!

xo, Sarah