I just got back from a similar length vacation last week, and I think that the Kaanapali area would be a better choice for one with children ages 7 and 8. I stayed on Wailea with a 3 year old, and while I love the weather (sunny almost 365 days a year) my wife and I discussed that we would probably go to the West side (Kaanapali, etc.) as he aged. Wailea has great resorts, wonderful restaurants, and good shopping (recent addition with the Wailea shops) but there isn’t a lot to do with the kids. In addition to having all of the things that Wailea has, the West side has even more for the kids. For example, most of the good boat trips (whale watching, Atlantis submarine, and other island ferries) leave from Lahaina. Lahaina shopping tends to be some of the best on the island and the restaurants are also superb. The only drawback is that it is more crowded and the weather isn’t quite as good. That last point is really “splitting hairs” though - come on, it’s Hawaii after all!

I also don’t like the idea of splitting time. It’s not that big of an island, though the traffic can look like Manhattan at times. Why waste a day packing, moving, and unpacking again? It is just too hard for very little benefit.

The Hana idea sounds nice, but I don’t know what I would do for more than one night there. Think about a hotel for a night or two at the end of your trip and head back to the airport from there. The drive to and from Hana is most of the experience anyway. While there is plenty of relaxation in Hana, there isn’t much else other than the usual tourist stops along the highway. If you decide to go back and forth on one day, leave VERY early in the morning - before daybreak. It has worked out best for us when we leave in time to drive though Paia as the sun comes up. Then you are ahead of the crowds on the switchback road. In my view, this is a must!

So with the kids, my vote would be Ka’anapali and west Maui. If it was a romantic trip for two, then I would go south to Wailea.

Have a great time. I am ready to go back!

I would go with no 2 definately, Lahaina is lovely much more Hawaiian we much preferred it to Kihei, the facilities are much better and it is much prettier. All the places you mention are within driving distance, we stayed up at Wailea, but drove to Kihei and Lahaina easily for the day, and up to Haleakula and Hana, why waste valuable time packing and moving, also I would say the beaches for kids that ages are much safer in Lahaina