When I went the hotel we stayed at actually comped us the car rental. Kuiaia (sp) was gorgeous but full of golfers and newlyweds. Oahu is very commercial but lots to do.
I wish we'd done Maui. Have you considered camping? I think you have to book a year in advance, but it looks awesome.

....

that said, i highly, highly recommend the trip, and agree especially with kaua'i.

cut costs on anything you need to over the next couple of years if you need to
i know that's not where you're looking to save money buy hey, whatever it takes, right?

the big island is, for my taste, too crowded and touristy. don't get me wrong, there's still plenty of good hiking and such, but i found the other islands much more to my liking.

btw, the seafood is, unsurprisingly amazing....

enjoy!

I'll PM you after work tonight with details,

But have been to Kauai a few times. You might want to consider a package deal that is all inclusive. Kauai is the least populated Island with beautiful sights and beaches. The upside to a resort is the pool. Most young families prefer pools over the ocean as it's safer and the resorts provide significant supervision and some even have activities designed for children.
If you were coming to Maui, I could provide more detail.

Or any of the Islands.

Kauai was the first that came to mind since my parents had experience with it and from pictures it looks breathtaking, but all of the islands look pretty incredible.

Via DM if I can be of more help, especially if you do decide to come to Maui. Some of the information that other DUers are offering you isn't exactly accurate or beneficial.

Both LAX and SFO are main hubs with all Hawaii flights on West coast going through them. OAK and SJC too. Look at major carriers like United, Alaska and Delta, but also on Hawaian airlines. Sometimes a multi city ticket with stopover is cheaper - but sometimes buying two separate tickets (i.e. Florida to California and then separate California to Hawaii tickets can be cheaper)

Fly mid week days - generally Tues, Wednesday and Thursday's are cheaper.

Food is expensive on island, particularly restaurants, but even a Safeway, so plan to go on that diet or buying the specials advertised. Eating out is really expensive.

Car rentals at airport are pricey. Try to take a shuttle from airport to a hotel near a condo. Then either walk to condo or taxi. You can always rent locally with a rental agency a car for a day or two and go explore the island.

Try VRBO or homeaway for finding the condo.

Consider Maui also as an option. Love Kauai, but Maui can be easier to navigate and find deals especially activities for the kids.

If you have young children, I'd really recommend either Oahu or the Big Island over Kauai.

Oahu has great, easy snorkeling places, a wonderful aquarium, great museums, a planetarium, plenty of rainforests and waterfalls, the famous "North Shore" surfing spots....I could go on and on. (And of course Pearl Harbor!!!)

The Big Island, of course, has the volcanoes!! Lots of ancient petroglyphs, ancient temples, spectacular colored sand beaches (black, green, and pink!).

Kauai is unmatched for beauty, for sure, but it is quiet and not very "family friendly". It has geared itself up more for the honeymooner and retiree travelers. That being said, I'm sure you could find stuff to do.

But, if you want your kids to come away with a knowledge about Hawaii and its people and history, I'd go for Oahu or the Big Island.

Take it for what it's worth....

If you plan on breaking up your trip...Phx might be cheaper to stay in than Los Angeles and certainly cheaper than San Fran. Most things are expensive in Hawaii as they have to be shipped /flown in. So think about putting together a bag of drugstore items you might need and bring them from home (cold medicine, aspirin, stomach ache medicine etc.). Also airport and on flight snacks can be pricy. Buy them at home and bring the treats with you to dole out to the kids along the way there and back.

Planning for a long dreamed of trip is part of the adventure, so you can never start to early!

stunningly beautiful. Small and easy to manage. We found a condo with Travelzoo....saved a ton. Stayed on the north side in Princeville, which might be the priciest part of the island. Kapaa or other areas might be cheaper. Definitely recommend using VRBO or something like it as well. Flights are expensive, no way around it. If you decide to overnight near LAX, hotels are pretty pricey, and not sure you want to scrimp and stay in a sketchy area.

Highly recommend a helicopter trip to see the island. We took Blue Hawaiian Helicopters. Again kind of pricey, but the experience is one for a lifetime. Large, safe helicopters, and our pilot was fantastic.

Have fun!

It was around $150 a day. Right on the ocean.

Had a full kitchen, cooked for ourselves.

We have been to Oahu, and Maui, stayed at hotels there.

It can get expensive, depending or where you go, and what you eat.

We liked to find small places that locals go to.

One of our favorite things was to find a good "Plate Lunch". A local phenomenon. The Rainbow Drive In is quite famous on the island of Oahu.

They can get also expensive, depending on location. It traditionally an inexpensive and filling squarish meal.
Scoop of rice, macaroni salad, and some sort of protein. Simple stuff. The Moko Loco is pretty famous, and there are several places that claim to be the "home" of the original. Research on the subject can be quite entertaining and educational.

One of the best we had was on Maui, right on the access road to the golf course there.

I can't remember the name, but it was really good, inexpensive, and very large portions.

In Oahu along the main drag there, there is an International Market, where there are quite a few good walk-up sort of Asian and assorted take-aways. It was very handy during the earthquake massive power failure about 10 or so years ago, as a lot of them cooked with gas!

I love Hawaii, but the tourists can get to you.

It is fun to find areas that are somewhat desolated, so that you can enjoy the scenery without distractions.

There are so many places to visit!

The worst part is the flight there, and heaven forbid that you get a long flight with bad seats, cranky babies, or unruly children. Had them all. Bring noise cancelling headphones!

I wish the airlines offered adult only flights for we empty-nesters!

= free flights anywhere SW goes.

https://creditcards.chase.com/southwest

https://www.valuepenguin.com/southwest-airlines-credit-cards

I don't have one because I no longer travel by airplane.

I think this time you just charge $2K and you get the points, then you can cancel the card.

I have a boatload of SWA points as they never expire. I don't use them much as I have my own airline.

I went to high school on Oahu, graduated in '68.
We would fly to Maui with our surfboards and sleep anywhere we wanted.
On the beach, on the piers, and on the greens of the golf course at
Ka'anapali, where the Japanese gardener would wake us early.
And Lahaina back then was fabulous.
But I would look into camping. I haven't been there in many years but I'm
sure there must be places. Ask Cha, she'd know.

TEACH YOURSELF AND YOUR KIDS TO SWIM AND SNORKEL NOW. PLENTY OF VIDEOS ON YOU TUBE FOR INSTRUCTION. YOU'LL BE SORRY IF YOU DON'T (YES I AM SHOUTING)

You are SMART to plan this far ahead. I always do.

I've been to Maui four times, always on a budget, always with kids. My last trip last summer was to celebrate my youngest daughter's 21st birthday. I had enough airline points to take us anywhere she chose. She chose Maui for a fourth time. (I truly think she'll move there eventually).

I've never done another Island aside from a quick overnight trip to helicopter over Kilauea volcano on the Big Island from out of Hilo.

First about Maui itself...

Don't spend less than 7-10 days there. Its not worth the 20 hours of air flight and massive jet lag unless you do. Its two whole days just to get there and back. And all the return flights that are affordable are red eyes. If you just go for 4 or 5 days you'll just be settling in and it'll be time to go home. Leaving Hawaii is hard enough and you'll just have to go back LOL.

There's PLENTY to do with little kids on Maui. There's an aquarium and tons of little sheltered coves and tide pools to take the kiddies to see and learn about ocean life. Depending on how old your kids are snorkeling is a must. You have plenty of time to teach them to swim and snorkel in a pool at home. Walking along Front Street in Lahaina is a blast with kids. It has lots of little shops and art galleries that my girls loved even as children. Day trips not to be missed; Drive to the top of Haleakala at Sunrise, the road to Hana, driving around the NW side of the Island for the big blow hole, shopping and a cool museum in Lahaina. The boardwalk in Wailea at sunset is not to be missed. If you go Dec thru March you'll see whales all over. If you can afford it do a whale watch or snorkel boat. The Pacific Whale Foundation https://www.pacificwhale.org/ has the best trips. My favorite is the half day to Molikini/turtle town. Do the morning trip, the seas get choppy in the afternoon which sucks for snorkeling.

Alaska, American, United, and Hawaiian fly nonstop to Maui from the US West Coast. Don't try to change planes in Oahu (Honolulu). With kids in tow you'll need a half way point to unwind between flights.I suggest LAX or PHX for a modern halfway airport with easy transfers and amenities for a long layover. Pack as much food as you can carry on the plane. Feeding kids in a airport is pricey. Bring empty bottles for water after you go thru security or you'll pay $5 for a bottle of water.

You have time to build up credit card points for one or two tickets. Use an airline card to pay all your bills, just be sure to pay it off by the end of every month. I'd of never made it there four times without saving credit card points.

DO rent a car. You'll be sorry if you don't. Even if you have to rent a tiny one, do it. Rent as big as you can afford. Plan to pay a dollar more for a gallon of gas so fuel economy will be important. Something with a hatchback or a big trunk is key.

A good base camp would be a VRBO or Air BnB condo in Kehei. Its centrally located, reasonably priced and you can be almost anywhere on the Island in less than an hour. Perfect start for day trips. You'll have a full kitchen which will save you tons of money, plus some private space if the "moment strikes" . Get a one bedroom with sofa bed for the kids. Two bedrooms is nice if you need another bathroom and are not much more money. A full kitchen and laundry are what's going to save you the most money.

About that kitchen, get a Costco membership. Food is EXPENSIVE even at the supermarkets. Stock up on a week's worth of food keeping in mind lots of it will end up in a cooler in the car. Think "lunchbox". Don't forget "Reef safe" sunscreen. (Yup sunscreen F's up the reefs) and laundry detergent. There's one right by the airport so go there first before you head to the other side of the island. [link:https://goo.gl/maps/6D9q6oeEnnF2|

Make sure you know what your condo includes. Many come with beach towels and chairs, boogie boards even snorkel gear. Make sure you have one with laundry facilities, saving space in luggage.

Now the cooler. After you drop your food and luggage at the condo and let the kids unwind at the pool or beach and one of you go to Boss Frogs to rent your island gear cheap by the week. https://bossfrog.com/maui/store-locations/south-kihei-snorkel-rentals/ Get a beach chair for everyone that has backpack handles and extra storage bag to carry stuff. You can roll a towel up in it and you're good to go. https://bossfrog.com/rentals/beach-chairs/

(they even have snorkel masks for people who wear glasses so you can see better)

If you can, get a cooler with wheels. You'll be glad you did.

Bring everyone a pair of these, you'll be living in them. https://www.amazon.com/s/ref=nb_sb_noss_2?url=search-alias%3Daps&field-keywords=water+shoes

Don't over pack. You can pretty much make due with one bathing suit and something light that dries quickly to go over. Do laundry at night. Don't pack anything you can't rent or buy cheap when you get here.

That's a lot for now. PM me for my phone number and I can tell you more.

DON'T BE AFRAID TO LOOK LIKE A TOURIST, NO ONE ELSE IS.

Tell your wife to leave her makeup at home. The light in Maui makes everyone beautiful.

Aloha!

Thank you so much. I'll let you know if I have any more questions as things progress.

That's me every time we go anywhere. I love to do the stupid touristy things. I like other stuff too when I know about them but I ain't afraid to put on a big Hawaiian flowerdy shirt and some linen shorts and flip-flops and drag my wife to the biggest ball of twine or home of the corn dog or whatever is the thing at wherever we are. We're going to Key West next month for our 31st anniversary and I'm a tiny bit bummed I probably won't even stand out lol. But I got a sweet hotel in an old building on Duval street and a big booze budget so we'll have fun.

And even though I'm not OP , thanks for this informative post. Hawaii is on my bucket list too so I'll keep this in mind for future reference.