We are travelling end of March 2013 with teenagers 13 and 15. We usually rent a condo or house on Grand Cayman or other tropical location. We don't do hotels because we need to wind down, read a book and occasionally explore a new town (require a bit more privacy).
We love walking to towns and exploring. We are travellers more than tourists and see most places we visit by foot, bike, care (in that order). Can you recommend an island (and location within that island) that fits this description?
I must add that we went to Maui without the kids eight years ago and stayed at a very nice resort. We found it unusual that most people we met, on or off of the resort, were from California and met few people who were of polynesian descent. We found locals at that time to be not very friendly. It was the most beautiful island though.