1. Stay in the Lahaini / Kaanapali area but rent a car. You can travel all over the island at your own pace cheaper then you can take tours.
2. Also check out Wailea. Wailea and Kaanapali are resort areas and hotels are a little pricier. No matter where you stay, rent the car as suggested and you can drive the whole island. Don't worry, it's not that big of an island.

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