It really does depend upon your skills level and sight reading ability. If you want to accompany, there may not always be time to have an advance look at the piano part. You could play in Care Homes, where I have quite frankly encountered some very low standard pianists who get away with it because no one expects much in the first place.
Poipu: Sunny Side of Kauai - See 72,655 traveler reviews, 6,044 candid photos, and great deals for Poipu, HI, at TripAdvisor.
When it's raining on one side of an island in Hawaii, though, the sun is usually shining on another, a short drive away. However, if the priority is to avoid heavy downpours in traditionally fun-in-the-sun locations such as Waikiki, Poipu, Kona and Kihei, the worst time to go is November through April.