I'm taking my teen daughter on a last minute trip (late August) and Maui or Kauai are considerations. We've been to the Big Island before and loved it, but have never been to the other islands and I am overwhelmed. Which part of the island to stay? What to do? We like (mild) adventure, beach and culture. For instance on the Big Island we went horseback riding, hiking, visited the volcano and snorkeled. She does want to learn how to surf and I would to also (I think) or at least stand up paddle boarding.
There are so many hotels on the islands I don't know where to begin. On the Big Island we stayed on an old sugar plantation in the small town of Hawi and loved it. We had to drive to the beach but on property we picked our own fruit, eggs from chickens and horses roamed free. It was magical. That is more our speed than a big hotel. I would not have liked staying in Kona. But since we will be alone this trip a hotel could be better.
We're also considering Todos Santos Baja Mexico.