Been along time reader, first time poster. Retiring after 32 years in education the wife and I want to celebrate with Hawaii vacation this Aug.-Sept. we are clueless how to go about it. We would take any info. Average budget I would guess always interest in saving lol, 5-7 days, would rent car for some of it. Thanks
Start by picking an island. There is a place in Omaha called Enchanted Honeymoons, they will book it all for you for free, they get kickbacks from the property they book you into. Doesn't have to be a honeymoon, wife and I used them for our Punta Cana trip and I was very happy with it. It will narrow down your options as far as properties.
I just got back, we were in the Kailua-Kona area (Big Island) for a bit and then Maui. Main difference is Maui has had more time without big lava flows, so it's more green, more vegetation, pretty beaches. The Big Island is still very active so you're going to see more fields of lava rock and less vegetation.
The resorts (Marriott, Hilton) are about 45 mins out of town in the Kona area, not many people understand that. You're up there in "gotcha" town with two hotels and a mall and the prices reflect that. If you stay in Kona itself, the prices are better. In town there's Costco, Walmart, Safeway close by. Get a Safeway card IMMEDIATELY or borrow somebody's phone number who has one. It will cut your grocery bill by 1/3 - 1/2, no joke. Groceries are expensive there as well.
My parents own a condo in Kona and stay there like 4-5 months a year now that they're retired. You can get condo rentals at a pretty reasonable price, especially outside school break times. In August-September you should be able to book just about anywhere for relatively cheap. You'll save a lot of money by doing some of your own meals. We usually do cereal for breakfast, sandwiches for lunch, then either dinner out or grill something. Lots of properties have grills on-site you can use. Everything in Hawaii is expensive and dinners out are no exception. But man if you like fresh fish...amazing.
Use Priceline for your car rental. I'll never rent a car another way again. Do the bid process and start just stupidly low, like $15 a day. Go up by a dollar each time until you get a hit. You'll be shocked how low you can book a full-size car. Gas is expensive there, fuel mileage is your friend.
If you like resort hotels, Maui is probably the better bet. There is a stretch along Ka'anapali beach where it's like 4 resorts right next to each other, if you didn't watch the signs you'd think it was all one giant hotel. Definitely more people, but also more options as far as eating, you can walk up to the mall, it was cool. The beach is much bigger, finer grain sand.
I could go on, but that's probably enough info to start you off.