Aulani and island hopping

If I don't island hop, I was just going to do a split stay in Oahu. Where I would be staying 5 nights near Wakiki at somewhere like Hilton Hawaiian Village or Outrigger, where I can do as much sightseeing as possible since that's where the heart of the sightseeing is. Then switching over to Aulani for the other 6 to have a more relaxed approach.
 
Another option would be to spend a few more nights at Disneyland. It's not hard to spend five full days seeing everything the Disneyland resort has to offer.

I already booked the airfare with my United Miles we've had months ago, so I can't really add or subtract days even if I wanted to, without losing thousands of miles.

I figured 5 days would be more than enough at Disneyland for me and the wife. Since it's only 2 parks, and most of the rides there I have seen going to Disneyworld so many times. So I would take a more relaxed approach to see the stuff that's Disneyland exclusive this moment.
 
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With that many nights you should definitely island hop. It is much too far to go to not see more than 1 island. Last summer we did 3 n at DL, 7 n at Aulani then 3 n on Maui. We always end on Maui (I have been 5x now). But I would say that THIS LAST TIME I wish we had finished at Aulani because there is nothing to compare to Aulani on Maui and we felt like we were downgrading resorts so much when we switched. NEXT time we will do Maui first then finish at Aulani. BTW, when we switched last summer we had like a 9:45 am flight so we were ON Maui by 10:30 AM and had picked up our rental car and were AT our hotel in Ka'anapali on Maui by Noon. Yes, island hopping takes a little bit of time but only about 1/2 of a day. Nothing that should deter you from hopping. Go early rather than later so you have plenty of time on your next island rather than smack in the middle of the day which feels like you're wasting the entire day.
 
I also vote for island hopping. While we loved Aulani, our issue was lack of restaurant options, so 4 nights was plenty for us. I would rather stay longer on Maui or Kauai, although usually Maui is better for first-timers, as there are more activities available than Kauai. I'm not a huge fan of Oahu, simply because Waikiki reminds me more of a big city rather than a relaxing getaway, and while there are quieter areas on Oahu, I just find the other islands less busy overall and have more lodging options that fit my criteria.
 


I island hopped the last time I did Hawaii, so that would be my vote. I spent a week on the Big Island, 4 nights at Aulani, and a week on Maui. If you book your tickets early enough, you can get really cheap flights on Hawaiian Airlines to the other islands. As OP have said, get an early flight out so that you have the majority of the day still available on whatever island you hop to. There is a lot to do on Maui, so do your homework and decide where you want to stay. I stayed in Kihei, which was close to everything I wanted to do except the Old Lahaina Luau. It was about a 45 minute drive to that. However, I had considered staying in Ka'anapali but the RCI resort that I wanted to stay in wasn't available when I booked the one in Kihei.
 
The only issue that's leaning me against island hopping, is that I would already been on a plane twice going from Newark to Lax staying at Disneyland, then leaving lax 5 days later to come to Hawaii. I would then be going on another plane when I go home.

My future wife seems against the idea since she doesn't want to deal with more planes, but I really would like to see Maui or Kauai.

Will be a tough decision that I should make soon before everything fills up.
Considering it took us two flights to get to Oahu (we're in Indianapolis so no direct flights), then a flight to Kauai 5 days later, then three flights to get home (Kauai to Oahu to Houston to Indianapolis), I guess I don't consider adding another flight a big deal! And we did that with 2 kids and my father-in-law, so just two of you is a breeze. That really is your personal preference how much you are willing to fly. We also traveled on United miles and booked a year in advance, so we booked the inter-island flights through Hawaiian Airlines and had a great experience. It's pretty cool seeing the islands on take-off and landing.
 
IMO, you'll need 7 days to fully appreciate the major sites on Oahu. There really is a lot to see and do. After adding in a few resort days at Aulani, you will need 7-10 days just on Oahu. So, an 11 day split Island stay will eat into Oahu time. This Summer we are going to Disneyland for 4 days (my kids have never been there), then 11 days at Aulani. And we plan on spending most of our days at the resort as we have been to Oahu (and Aulani) 3 times with the kids and have already seen the main sites. On previous trips we have done split stays that included Maui, Kauai and the Big Island - so my opinion is based on my personal experiences. (And BTW, when we booked using United miles on our last trip, we flew Newark->Maui and returned HNL->Newark. This is the same amount of miles as flying round trip to HNL).
 



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