Your itinerary sounds great!
Great, thanks! Hopefully I'm on the right track and can just improve it a bit from here!
*Highly recommend the malasadas from Leonard's. They are very filling so we bought a large box and were able to eat them for breakfast for a few mornings.
Oh, that is good to know that they were good on other days, as I wasn't sure about that. Did you warm them up or refrigerate them or leave them out? I'm sure we'll want to try some fresh ones, but won't be up for eating a whole box upon arrival. Leftovers are good!
*I do believe you can cancel ADRs at any time. When we were there last September, it was so empty that every time I went to make an ADR somewhere, the CMs were telling us it wasn't necessary. Always nice to have though as a Disney planner. 
Yeah, I figure it can't hurt to have them, since I have read reports of people having trouble with walk-ups and last-minute ones. I like the cancel anytime policy, though!
*I like your idea of the swap when you go to Pearl Harbor. It really isn't toddler friendly but in my opinion, a place where everyone should visit when on Oahu. Just remember, absolutely no bags allowed. So many people were sent back to their cars to drop off their bags, including purses. Because of this, they have a high crime rate of car break-ins even though there are security/police patrolling.
That's part of the benefit of splitting up - the swap meet person can have all of our stuff in the stroller and the Pearl Harbor person can just have whatever they need in a pocket. Much easier than worrying about break-ins!
*We had dinner at Ama Ama once on our anniversary evening, watching the sunset which was nice. Very expensive, but nice. Make sure you request a table near the edge, since there are no windows, all open air. Gorgeous view. We also had breakfast there twice because the stuffed french toast was divine and kept DH & I full for most of the day!
Great advice. And I had wondered if that French Toast was good, as the description sounds yummy. Okay, I just went and reserved Ama Ama for 9am on our totally free day (11/14). Yay!
*The Menehune Trail game was fun, very Kim Possible. They give you an iTouch so its a bit difficult to see in the direct sunlight but a nice fun distraction.
That sounds like our kind of thing! We (especially Dug) enjoyed Kim Possible. I think Izzy might get a kick out of it too.
*If you want to make sure Dug gets a chair at the Starlit Hui, I recommend lining up about 20 minutes prior. There are a limited amount of chairs and you can just request to sit in it when you walk into the grass area. CM will escort you to the seat.
Great, thank you! We will try to do that for sure!
*We went to the Dole Plantation but only to eat a Dole Whip 
. We did buy some t-shirts but nothing else was appealing to us. Does sound like Izzy would love to ride the train though!
Mmmmmm, Dole Whip!
*Be prepared for long lines at Matsumoto's. They do a very good job at being organized though and have it down to a science with taking orders with one person and waiting for your number to be called. We were too chicken to get the beans on top (ew!) but the shave ice is so much cheaper and you get a much larger portion here than at Aulani. Plus its a landmark!
Maybe we will have to each get one and share - one with beans and one without, maybe? It seems weird to me, but I know some people swear it's amazing, so I feel like I should at least try it.
*We made it to Monkeypod one evening for happy hour. Nice walk down the street from Aulani. Also expensive but happy hour was reasonable for apps & drinks. Wonderful atmosphere even though its on a busy road. We never had to make ADRs.
Good to know. I think I might try to make reservations, but not until we get there. Just in case - I'd rather not keep a hungry toddler waiting.
The happy hour menu seems decent in selection and price.
*Waimea Falls Park is a historical botanical garden so there is an entrance fee, FYI.
Do you think it's worth seeing if we don't care to swim under the waterfall?
*DH & I did the 2 hr horseback riding tour of Kualoa Ranch. It was AMAZING! Obviously Izzy won't be able to do it but there is so much to see on the ranch that even if you don't book anything, in my opinion, its worth a trip there just to visit. Such gorgeous grounds and you can walk around and see the horses. Wonderful staff there as well.
The horseback ride sounds really fun! Hoping the movie tour gives us some nice views too and we can take in all the beauty of the place during our visit.
*If you are looking to try the Loco Moco, I've heard that Rainbow Drive-In has the best.
Good to know. I'm not sure if I want it, but I figured the breakfast buffet is a good way to try one version of it and see if I want any more after that.
*When heading to Diamond Head in the morning, remember traffic. Traffic heading into Honolulu is insane but it moves. Unlike traffic here in MA, its bearable. Cars move, no one, I mean NO ONE beeps their horn and everyone is so laid back and friendly! If someone wants to change lanes they use their directional and then say thank you. Its awesome! 
That's a good point, since it won't be on a weekend. I am hoping to leave really early, though I need to figure out what time "really early" is. Sounds like similar traffic to what we have here in MN, but even nicer than our "Minnesota nice" (passive aggressive).
*We ate lunch at Uncle Bobo's BBQ one day. What a great hole-in-the-wall place! The pulled pork sandwich was delicious! Highly recommend if you have a chance to stop.
Sounds right up our alley! I asked Dug if he was interested in a BBQ place and he was very excited!
*The lounge inside Aulani to use after check-out is fantastic. Showers, lockers and even a spin-dry machine to dry your bathing suit prior to storing it in your luggage. There is a computer there as well to use and a TV displaying flight times out of Honolulu airport. They did a great job with it.
Sounds really good! I read something indicating there were weird policies about coming in and out just once and it was difficult to manage - did you have any issues?
*We did a lot of driving around the island to explore. We are huge LOST fans so I made a doc of all the places they shot at. Let me know if you'd like me to share this with you.
Yes, that would be fantastic!! Not sure how much we'll get to, but we did watch the entire LOST series (most of it all at once on Netflix, right before the final season). I know Dug would enjoy seeing some of those sights, if possible. I'm actually really excited about just driving around. I love to drive through scenic places!
*We went snorkeling at Hanauma Bay one day which was a lot of fun. There is an entrance fee pp here but I believe it was only like $5 and the money goes towards maintaining the area.
It does sound really nice. I'll have to check with Dug again to gauge his interest in snorkeling. For whatever reason, I'm just not that enthused, but I've only snorkeled once before (on a cruise excursion) and I got some nasty coral scratches, so I'm sure that's coloring my opinion.
*Other place to check out is Pali Lookout. Gorgeous view from up there.
Great, thanks! Would you work that in on the Punchbowl, etc. day?
*Make sure you just enjoy down time at the resort. Its such an amazing place to walk around and take in all the details. I bet Izzy would have fun finding all the Menehune hiding around! There is also a nice path behind the resort that you can walk up and down the coast. Very nice to talk at your leisure in the evening when its cooler.
Sounds so nice!
I hope that isn't too much information. I know how overwhelming it was when I was doing the planning so anything I can do to help others I'll try! 
Not too much at all! Thank you, thank you, thank you!
I feel like I need all the help I can get on this one!
One reason I love traveling to Disney, is because I know how to plan for it. I wouldn't have any idea where to begin planning a Hawaii trip!
You hit the nail on the head there! That is exactly how I feel!
Very cool that Izzy is watched by a Disney enthusiast
We're very lucky! Our daycare provider is often wearing Mickey socks and such! We didn't know when we interviewed her, but saw a Disney trip collage on our way out that tipped us off. Didn't realize how into it she was until later, though.
Look at all these plans! I forgot that you're going to be there for 10 days
I know, this is the longest trip we've had in a very long time! But I think that's good, as everyone says you need at least that long in Hawaii, after flying so far.
Hopefully that overnight flight back home won't be too bad.
I hope so too. Funny thing - believe it or not, I did not even realize it was a red-eye until like the day after I booked it!
It was such a frantic buy-these-ASAP time that it didn't even register with me that the return date was the next day. But I think they pretty much all are overnight flights, so I don't know that I would have changed anything.
I'm looking forward to seeing how this trip turns out. We'd like to get to Aulani for our 10 year (hopefully!) and not sure if it will be with or without DS. But at least i'll get ideas from your TR, along with Mark's and Cynthia's.
When is your 10-year? I'm sure it would be a good trip to celebrate! We are going about a month after our 9-year, so I figure this is kind-of an anniversary trip. I love gathering ideas from other TRs!
My husband and I can't believe the deal you got! We are so jealous! We were at Aulani this past May with our 3 1/2 year old son. We had a great time, but when I got home, I said I would never bring a three year old to Hawaii again! Life with a toddler is a lot less planning and more just wait and see. And our son is a super laid back kid, but there were several times when we didn't do what we wanted, or what we thought we were going to do, just because it wasn't working out like we had "Planned". So just remember to keep your plans very flexible. We spent a lot more time at the resort sitting by the pool then we had initially thought, just because it was so nice and relaxing, and everyone was enjoying it. We also ate a lot more at the resort, because it was easier than leaving. I wrote a detailed trip report on my blog, link is in my signature. If you have any questions from a been there done that took a toddler to hawaii Mom, just let me know.
Good luck with the planning, and I can't wait to read your trip report when you get back.
Yeah, that deal was just ridiculous!
In a world without a massive airline price glitch, we wouldn't bring a toddler to Hawaii either. We would have gone when she was older, probably. But, I can't imagine leaving her home for that long, so we'll just have to stay flexible, as you said. Luckily, we've had some chances to practice with a lot of travel this past year (WDW x 3, NYC, Portland), so that gives us some idea of what to expect and what kind of traveller she is (pretty good!) But I know that our plans will deviate - they always do. This last trip to WDW we ended up doing a ton of unplanned character meets, since she suddenly decided she loved them. (I'm sure that will happen at Aulani too - must meet Minnie every day!
)
I just peeked at your blog and realized that I ran across it somehow earlier in my planning and read/skimmed it then. However, I am going to revisit it soon and read it again, knowing more about what we're planning at this point. I appreciate the help of someone who has been there and done that!
...and I think Andrew would be pretty much out of luck, unless he can fit in luggage. 
We had the good luck that got us this trip in the first place. Great timing – looked at airfares at just the right moment. 
Now we have the lousy timing that has made me re-plan our entire trip less than two months out. Don’t get me wrong, the reason behind the change is an overall good one, but also a huge bummer and a very unfortunate timing coincidence. This pre-trip report needed more drama, I guess.
I am on pins and needles waiting for flights to be confirmed, though – hoping they will maximize the amount of time he has with us in Hawaii while still getting him to/from the retreat in a timely manner. 
I actually felt much more of a loss than I anticipated when he accepted the offer, knowing he’d miss over half of our trip. But it is what it is and we’ll make the most of it. I guess it’s good that I’ve done the two WDW trips with just me and Izzy – not too concerned about it just being us while he’s away. Though it does make it more difficult to do certain things (i.e. – no waterslides). I’m sure we’ll do a ton of character meets, though. 
Then head out to the North Shore for a “movie tour” at Kualoa Ranch, probably mid-morning (need to reserve this still). After the tour and a quick look around, head to lunch a few minutes away at Uncle Bobo’s BBQ. After lunch, head a bit further along the shore to the Polynesian Cultural Center. Arrive shortly after opening at noon, then tour the place while Izzy naps in her stroller. After spending the afternoon exploring the place, head back towards Aulani. If it’s before the 5pm closing time for the Dole Plantation, stop for a snack and a train ride. Eat dinner at Kua Aina Sandwiches near Aulani, then back to the resort to get Izzy to bed and switch off trying the slides and the lazy river before they close at 8pm. Could also switch off at hot tubs or main pool until 10pm.
