As to the island we chose, we just guessed and went with Maui. We were told that Maui and Kauai were both the best islands by friends and so we just picked the one that a friend had given a recommendation on a condo. We loved Maui. Next time we'll try Kauai or another island, I'm positive they are all idyllic paradise.
We stayed at the Kihei Beach Resorts found here http://www.kiheibeachresorts.com/. It was a delightfully quiet little condo at the very north end of Kihei. South of town is very busy so this seemed more in keeping with our quiet ways.
Staying in a condo has many advantages. Obviously having a kitchen can really save on your food bills which was a larger expense. This condo had a small fresh farmers market that had wonderful fruit and vegetables. They do have a Kmart and Walmart on the island so stock up there for cereal etc. The little stores are like here and can be expensive, but we found the grocery stores reasonable when you remember everything has to be shipped here on boats!
Our favorite experience had to be the helicopter over West Maui and Molokai. At first we balked at the price but then realizing we would probably never be able to return we sucked it up and went for it. Choosing the service and trips was challenging. There are many helicopter services and several different trips but we loved the one we chose. We saw rainbows, mountains, waterfalls, and even whales. It was very cool. We flew with Blue Hawaiian Helicopters and our pilot, Tim was amazing. He had this lovely calm voice and was knowledgeable about the history and inhabitants of the islands. I'm not sure which was my favorite the rainbow, waterfall or whales.
Another activity our son and his girlfriend enjoyed was surfing. They had lessons from a man by the name of Sasha who works for a company called the Maui Beach Boys. He was really patient and they got up on their first try. They really recommended him. Just so you know, they don't take credit there. There were a surprising number of places that didn't take credit. You need to carry cash.
Our favorite restaurant was recommended to us by a nice little couple from Ohio we met waiting for the helicopter. Mama's Fish House has excellent food and the atmosphere is not to be missed. Is it expensive -- Yes, but well worth every penny. The food was probably the best I've ever had at any restaurant. They had fish caught that day, steak for those of you who don't like fish, and a dessert to die for. Strawberries in something like clotted cream.
Another thing we think you must do is a luau. We looked at several and would have liked to try a few but what we finally went with was the Feast at LeLe. It was a delightful evening centering around a dance and dinner course from Hawaii, Aotearoa, New Zealand, Tahiti, and Samoa. We probably wouldn't have tried some of these items if just offered. They differed from our usual fare but we really enjoyed it all. They have a professional photographer who offers photos on the beach and a local artist who will personalize your favorite tiki. I know it's another unnecessary expense but what a great rememberance to bring home. In the midst of a Minnesota winter I will look at it and be reminded of those days in the sun--a thing worth it's price when it is 10 below.
We didn't end up doing the full road to Hana but we went 10 or so miles. We turned around when someone thought they could go faster than the speed limit and ended up in our lane coming at us around a curve. We decided other people were a hazard we didn't want to deal with. We ended up turning around and visiting a twin waterfall. We walked along an irrigation wall back to this delightful secluded area. You can swim in the pool but we didn't.
If you are on the island from December until April you should try the whale watching tours. I don't normally get motion sick on a boat but it was a very windy day. Seeing the whales was worth the trouble though. It's not every day you will see something so magnificent in the wild.
The last day we were on the island we decided to drive all over and just see everything we could. It was one of our best days. We saw the Iao Valley, Tedeschi Winery, and then just drove and stopped as the whim caught us. Finding a deserted beach was just one gem.
This is just an overview of items we did on our trip. Shall we say the best of the best. One thing I will say is that I'm glad we did it. You never know if you will be here tomorrow so you need to remember to live for today.