re: Hawaii vs Caribbean Upscale Resort Trip

No way are the locals worse in Hawaii than the Caribbean. I love the Wailea area of Maui. It has 4/5 star hotels right on the beach, condos, shopping, restaurants, golf all in the area. Plus it's a short drive to a lot of other areas on Maui.

Kauai is also great. A lot of people like it more than Maui. It's a completely different vibe. I recommend the North shore / Princeville area if you are going in the summer, but the south end/Poipu area is also great. As others have mentioned, you could split your stay between the two areas on Kauai.

So many places to choose from in the Caribbean. Little Dix, Caneel Bay, Grace Bay, Jumby Bay are just a few of the resorts or resort areas.