This year Christina and I went to Hawaii, Maui specifically. No need to be more specific than that since 80% of the island is less far away than my daily commute to work, so effectively just down the road.
We stayed north of Lahaina, one of the larger towns on Maui, which sits on the western coast of Maui. If the goal is less clouds, it seems it’s best to stay on the western coast or the southern coast as the mountains seems to play cloud catcher and provide some protection from the weather on the lee side of the mountains.
The weather was wonderful, high 70s to low 80s every day. Usually some high clouds in the sky, often just passing through. We did have a couple of days that were cloud free blue skies from dawn to dusk and those days were spectacular!