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.
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Where you go depends on what you want to do - Oahu is great for shopping & nightlife. Kauai is great for hiking, but Feb and March can be very wet over there. The Kona side of the Big Island has lots of self-contained luxury resorts if all you want to do is sit by the pool and relax. Maui is a condensed version of Oahu.