Hi Kirstie!! So thankful to the Pollys who summoned me.

How exciting! Kualoa is owned by dear friends of mine and they will treat you well. Haven't been to Duke's in 18 years but it was fun (and crowded) when I went. Lots of memorabilia. On Sundays,
Henry Kapono plays live there and he's a musical legend on the island. (If you can't catch him live, he usually livestreams his sets on his Facebook page.)
My very favorite beach is a tiny beach called
Kaiona, which is on the east side of the island. Some might call it Waimanalo beach but it's a little ways away from there. Avoid on weekends-- lots of locals have big celebrations there-- and try to get there as early as possible (at sunrise on M-Th, you will usually be one of the only people there). I see turtles there all the time when snorkeling and it's really beautiful (see photo). If you want to see a good sunrise, you can go there or to Sandy's or Makapu'u beaches (also on the east side). There are lots of locals living and working nearby and not a lot of tourists. The locals are humble and kind and appreciate it when tourists keep a low profile.
Going around the island can be so fun and beautiful and because of two lane roads, it can also be fraught with traffic so it's good that someone else is driving. There are lots of places that are well-known but because of this, they are loaded with tourists (like Matsumotos shave ice in Haleiwa). They do pretty good crowd control there but if you don't like crowds, stick with recommendations that are off the beaten path. Like if you want great shave ice and you do make it to the east side of the island,
Kokonut's is a great place to go.
Lots of east side recommendations because that's where I grew up and where my family lives.

I don't do a lot of touristy things but most opportunities are great and super fun. Reach out to me if you have any other questions. Aloha!