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> Not to get too flyertalk-y, but what rental company? I'm crossing my fingers w/ National as an executive member that they'll have a convertible or something decent (fun) on the aisle.

• I paid for my entire trip with points/miles. All the car rental companies are very similar. I used Budget since it was the cheapest. The cost was ~3,338 pts/day using my Sapphire Reserve through Chase's booking site. (YMMV)
  
  
• /u/manachar made some great points from a local perspective. However, I don't think renting a convertible is impractical for visitors. Driving around a beautiful Hawaiian island with the top down was a wonderful feeling and I wouldn't want it any other way. But that's my preference. I'm from the midwest where people appreciate any opportunity to feel the warm open air when driving.
  
  
• Car theft is a problem in many areas of Hawaii and nearly all Mustangs/Camaros are being driven by tourists. However, a little common sense goes a long way. Don't walk away with the top down. Don't keep valuables in the car.
  
  
• Also, a general point to consider is what you'll do with the key fob when you go to the beach. I did not want to leave my belongings on the beach unattended, so I bought a Pelican 1010 case to keep my key fob, cash, and cards dry when snorkeling.
  
  
• A majority of the roads are in great condition. Some back roads and parking lots can be rough but I never felt that the Mustang was incapable of handling them.
  
  > I'd like to as I've heard good things, and some of the stops (e.g., waterfalls) seem interesting, but I'm not sure if I'm up for a day-long drive or doing this as an overnight trip. I might look into one of the tours
  
  It was a great experience but over-hyped in my opinion. I would still recommend it. There are several beautiful waterfalls, cliffs, distant scenic landscapes, and hikes (although most hiking I did was in West Maui).
  
  > I've heard! I guess that's a perk of this being a work trip!
  
  In that case, check out Mama's Fish House! It's costly, but worth it. You'll need to make a reservation days in advance.

Can't speak to your Oahu itinerary, but I can provide my two cents on Maui.

Day 6: We did the Old Lahaina Luau and it was great, very highly rated. So if you haven't already booked Lele, I'd compare the two.

Day 8: As for Haleakala, you don't need a tour, assuming you have a rental car. Just drive up the mountain and grab a spot. Start early, though. There's usually a line of cars winding their way up in the wee hours of the morning to catch the sunrise. There's a fee to get into the National Park, but that's all. There's also some hiking you could check out up there. EDIT: I've learned from other commenters here that you do need a reservation, my apologies! More information here.

Day 9: We didn't do any whale watching but did take a snorkeling cruise to Lanai with Trilogy. I'd highly recommend the company — very professional, great service and an all-around good time. And they also have whale watching.

Day 10: We didn't use an app for Road to Hana, simply picked out what we wanted to see ahead of time and made adjustments along the way. Again, start early. If tour buses are catching up to you, things will start getting real crowded real quick.

I'd actually encourage some open days to just chill, so your whole trip is not go go go. But you could fill in part of one of your days with snorkeling at Honolua Bay or check out the Maui Ocean Center.

Day 13: Ali'i Kula Lavender Farm is cool, but we found it to be an hour's diversion at best. YMMV, of course. Mama's Fish House is dooope!

And I'd say Maui Revealed: The Ultimate Guidebook is worth a purchase.

Thank you very much! I booked a hanauma bay tour for friday morning! My wife is super excited!
Also we're planning on getting a couple tubes of this this sun screen and after reading your linked article it seems I have to be very wary of what the package reads as it maybe "lying" to me. So we went ahead and ordered a couple more rashguards each from amazon (we already got a few after reading some other posts here). Thank you again for your help!

I concur with the others. Save the other island for another trip. Maui is probably better for most honeymooners, but unless you really hate nature you're going to love Kauai for the 6 full days. Get the The Ultimate Kauai Guidebook: Kauai Revealed and choose your activities. I recommend the Smith's Kauai Luau.

Kuni's dry goods? I think they're just called Kuni's now?

Oh wait, to collect not to use? I don't think I've ever found a Hawaii souvenir thimble.

Enjoy your visit and buy this when you get back home:

https://www.amazon.com/Hawaii-State-Souvenir-Collectible-Thimble/dp/B00QT5G92S/ref=asc_df_B00QT5G92S/?tag=hyprod-20&linkCode=df0&hvadid=216539702338&hvpos=1o1&hvnetw=g&hvrand=2362536972144242853&hvpone=&hvptwo=&hvqmt=&hvdev=c&hvdvcmdl=&hvlocint=&hvlocphy=9032168&hvtargid=pla-350802331671&psc=1

No, nowhere to lock things up. Leave almost everything in your hotel room. Get waterproof cases or dry bags for phone, room key, cash, etc. If you leave it on the beach, count on it being stolen. Something like this https://www.amazon.com/gp/aw/d/B00LBK7OSY/ref=pd_aw_sim_200_1?ie=UTF8&dpID=41A3a0xk9xL&dpSrc=sims&preST=_AC_UL100_SR100%2C100_&psc=1&refRID=JXB5K8C8ERA52R9K47AF

The only place I've seen with lockers is Hanauma Bay and that's not in Waikiki.