First time to Hawaii - Which Island(s)?
 

We are a couple turning 40 and leaving our 3 kids behind to celebrate our birthdays and 15 year anniversary in Hawaii. We are traveling from the Midwest and are reserving 2 days for travel there and back with about 7 days on the islands (9 days total). We could potentially add a day or two but are trying to balance placing too big of a burden on grandparents that have to deal w/ our animals kids ;). If 1 or 2 days makes the difference to get to two islands we could push for it.

We are debating on three options:
1. Maui only
2. Maui + Kauai (thinking 5 days maui and 2 days kauai)
3. Maui + Oahu (thinking 4 days maui and 3 days oahu)

We want to mix some super memorable adventures with relaxation. We used to travel internationally to places like China, Africa and South America and are looking to add that adventure back into our lives even if just for a week. Are we crazy to try and fit two islands in? Here are my initial thoughts on these 3 islands in terms of what stuck out in case this gives some perspective on what we would like:

Maui,
The road to hana looks beautiful, definitely want to do the volcano, and the snorekling at the Molokini crater are top attractions on our list. Possibly an ATV Tour? What are the other must do's on Maui? Any hidden gems/beaches that are incredible? I've spent a lot of time looking at stuff but it's all starting to blur together. Ho'oilo House looks like a great spot on Maui (except queen bed? really? :)) so looking for other unique, ocean-view places like that on either Oahu or Kauai.

Kauai
the Napali coast looks incredible and we are considering a helicopter tour even though it scares the crap out of me. The fairly recent helicopter crash makes me a little weary. My wife can't handle rough water so not sure a coastal boat tour is an option for her if we did Kauai.

Oahu
We don't really care about visiting Pearl Harbor like most people so we are fine missing that. The North Shore sounds really cool. The Jurassic Park filming location sounds cool and maybe an ATV type tour would be fun.

From the three options you listed, I would pick #1. Mostly because I think your time is too short to try to fit in two islands. Or maybe do Kauai only? I love Oahu (nothing to do with Pearl Harbor) but doesn't really sound like you are all that interested. aloha, suze

What month?

Maui is my least favorite island but it is a good island for first time visitors.My favorite island is Kauai but time of year matters, as the boat tours of the Napali Coast go out year round from the southwest but only go out April-May through early fall (normally) from the north shore. Tours leaving from the north shore get to the coast in a much shorter time. So time of year matters.
I've done 7 boat tours and only two heli toours and IMO you get more bang for your buck on the boat tours.
If your wife is prone to seasickness, skip a tour on an inflatable and take Bonine the night before and day of.

On Maui I lied driving around upcountry and was totally bored by Road to Hana. The volcano is cool to drive up and see.

Also look into the problems with car rentals during peak travel seasons. Kauai, even off season is $100 a day. Maybe completely unavailable in peak season (same with the Kona area). If you are just going to stay at a resort then I might chose Kauai. In rainy season with no car, it would probably be at the south shore (Poipu).

I did not even look in to going to Maui. Even 25 years ago there were too many high rise condos on the dry side.

Whatever island you decide on, with 7 days, I would stay on one the whole time. Last time on Maui, we did an atv tour with Maui Off-Road Adventures that we enjoyed a lot. We also did a sunset cruise which was nice. On a previous visit to Maui, we took a helicopter tour through Blue Hawaiian. It was amazing and a once in a lifetime experience (I say once in a lifetime because, based on the record of crashes - particularly the one shortly after our visit that involved the same tour and pilot that we had and that killed everyone on board - I probably wouldn't do on another. But like I said, it was really a great experience).

I have yet to go to Maui, but I've been to Oahu several times, and I've been to Kauai and the Big Island. By far my favorite is the big island, which sounds like it would be exactly what you're looking for based upon the type of trip you described. The big island was not very populated, easy to drive (although some of the distances can be very long). We hiked down the jungle and onto the crater in Kilauea Iki in volcanos national park, and it was stunning. Broken black lava fields with steam bubbling up from the ground as you explored the crater. You could also get really adventurous and drive up to the top of Mauna Kae, where you can find snow during some parts of the year. Our favorite was kayaking across the large bay to the Captain Cook monument. Beautiful and fairly remote, the tiny beach has some amazing coral reefs right from the shore.
For Oahu, there are lots of hikes just outside of downtown Honolulu. The Aiea loop trail was easily done in an afternoon and you can even see some scattered remnants of a WW2 B24 bomber. the trees in this hike are spectacular and you traverse to some nice vistas and also down into a small stream in the valley floor. . The coral reefs on Oahu weren't as nice as the big island, at least the ones accessed by the shore. We did the ATV tour in the "Jurassic Park Valley" as you mentioned, and it was a really fun afternoon.
For Kauai, we really enjoyed the laid back feel of the island. We spent most of our time on the Princeville side, and it is very lush and tropical. We really enjoyed driving in the countryside and crossing the many one lane bridges. It was no problem pulling off on the side of the road and finding a beach all to your self. We did visit tunnels beach to try and snorkel from the shore, but the currents were extremely strong. Glass beach on the other side of the island was fun to try and collect little bits of sea glass as the waves rolled in. We did take the helicopter ride over the Napali coast and it was spectacular. I don't think you can really get to the Napali outside of the helicopter, boat or really long hike.
Hope this helps!
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Napoli is in Italy.

LOL, I'm terrible speller, and autocorrect didn't help me much here.

It would be hard to reach from Kauai, even by helicopter!

Ha! That it would be.

We ended up extending our visit to 13 days and are doing both Oahu and Kauai. Will share back any tips or highlights that are worth passing along upon our return. Thanks all.

Thanks for getting back to us about your decision. Still not clear on what month. My DW and I have been to Maui (first trip) and Oahu (last November). Our DD and SIL moved from Maryland to Oahu last year. We stayed with them for a week. We had a rental car that we picked up at HNL airport. I did drive up to the north shore twice from their place in Ewa Beach. There are a few things to see up on the north shore but few lodging options.
On our trip to Maui, we stayed in a small condo within walking distance of the beach. We did get up to Haleakala for sunrise the day that we left the island. The other natural wonder that we saw on Maui was the Io Needle.
Our DD and SIL recently took vacation from Oahu to Kauai and loved it. I don't think they rented a car.

Since you chose Maui and Kauai, I would start Maui and end with Kauai. Maui is beautiful and nice, but it's touristy and more hectic than Kauai. Kauai will give you the 'revved down' feeling you likely want.

They are doing Oahu & Kauai (not Maui) :-)

Ah, whoops, thanks for the correction.

In that case, they should definitely do Kauai second, and when in Oahu plan on leaving Waikiki every day. Stay there at night, but do day trips on other parts of the island.

Why do they need to leave Waikiki every day? There is so much to see and do in Honolulu as well as other parts of Oahu.

Waikiki is packed. There are so many beautiful beaches and hikes on Oahu that are worth seeing. Waikiki, meanwhile, is crowded and less scenic than, say, Lanikai. My dad loved Waikiki because it's great people watching, but assuming they 'want to see Hawaii' I would say stay in Waikiki but plan day trips every day.

I was in Waikiki for 10 days just in May this year (my 7th trip). I don't rent a car and travel solo. And find plenty to do. Not saying people shouldn't get out to see the rest of Oahu, only that personally I wouldn't want to get in the car every single day. I like to relax, and there's a lot you can see on foot right in and around Waikiki. The Bus makes it easy to get to things in downtown Honolulu as well.
aloha, suze

You can definitely enjoy Waikiki and walk down to Kaimanas or take the bus to Kakaako or even out to Hanauma. It's a matter of preference. For me, I think what the rest of Oahu has to offer is so much better than Waikiki I think it makes sense to get a car and head to the North Shore or Electric Beach, etc.

They could also stay at Kaimana Beach Hotel or the Lotus and avoid the sh*tstorm that is Waikiki.

Don't forget your reservations if you wanted to go to Hanaumu Bay plus it's now $25 per person. You also need reservations for Diamond Head.

what the rest of Oahu has to offer is so much better than Waikiki

Just a matter of personal opinion. I don't thing it is "better". Just depends your interests.

I love the classes, music & dance, performances, farmers markets, etc. all right in Waikiki daily.

Agree to getting out an see things, but not a reason to avoid Waikiki/Honolulu when there is so much, unique, to offer.

Those two hotels are on a fine more quiet beach, but not cheap, and no pools at either.

I didn't even get started on the list... Iolani Palace, Foster Botanical Garden, ShangriLa Estate, Honolulu Museum of Art, Plantation Village, Queen Emma's Summer Palace...

It sounds as if the OP's preference is for scenery, snorkeling, and they never mentioned museums, while specifically expressing no interest in Pearl Harbor.
I would recommend leaving very early from Waikiki to get parking at the North Shore beaches and pullouts that don't have parking reservation systems. At least the reservation system at Hanauma Bay helps with that. Stop at the Halona blowhole when you head out east too. Lots of nice little beaches with viewpoints along that whole shoreline heading east from Waikiki and around to the North. Also check one of the shrimp trucks and Palaa Kai Bakery.

On Oahu... A fun loop with a rental car is... Byodo-In Temple Ho'omaluhia Botanical Garden, Kailua and Lanikai beaches, Pali outlook. Have lunch at Buzz's Steakhouse in Kailua. Can be done in a half day from Waikiki.

I'm curious what OPs hiking experience is. There are a ton of good hiking trails very close to Waikiki (in the East Honolulu area) but if they aren't used to hiking or aren't in good shape, they may be a bit too much. Kauai also has a ton of good hikes, depending on how fit OP is.

I prefer Punchbowl over Diamondhead.

North Shore is fun, and Sharks Cove is a solid snorkel.

Would be curious on more guidance to know what to recommend.

Good comment from dougharper5625. One thing to be aware of is that on Oahu, some hikes are very exposed, no shade at all (such as Diamond Head and Kaena Point). Others can be muddy and slippery with exposed roots and shouldn't be done after a rain. Diamond Head also requires a reservation now.

By Punchbowl, did you mean the National Memorial Cemetery?

Have you ever rented a car in Hawaii, suze?

No. I was with a friend who lives there, she drove us to the places I mentioned above in May of this year in her car.

Yes, the National Cemetery. I haven't been up Diamondhead since they put in the reservation system, but while it's kind of fun going through some of the old tunnels and steps, the pay-off is really the view from the top and I think the view from the top of Punchbowl is equally as good without the massive crowd. It also has the value of a neat war mosaic and being a pretty scene on its own.

I know you didn't ask me, but for car rental I'd look at Turo. I've had the best luck with them.

For car rental I'd look at One's. On Seaview in central Waikiki.

Have you figured out where you caught the 'Rona yet? (suze recently disclosed that she came back from Oahu with an unwelcome souvenir). Waikiki is extremely crowded, even outdoors, as mentioned above.

Fortunately when I went people still took things seriously, and you needed to show a vaccine card to fly in, and to eat inside restaurants.

What do you mean "figured out". I've known all along. By the timing I believe it was from airport(s) and the plane ride on my travel day. I did not get sick until after I got home.