Gregory Cool by Caroline Binch (1994, Dial Books for Young Readers).
I really enjoyed this book about a boy who goes to stay with his grandparents in Tobago for four weeks. At first Gregory isn't too happy about having to stay in a little house with no TV, hot climate, and food too unusual and spicy for his taste. But eventually he starts to have fun with his family. He gets the nickname Gregory Cool because his reply to everything is "cool". I like how Binch captures the feel of the Caribbean, as well as Gregory's struggles to adapt from America. In the beginning of the book, there is an illustration of his parents saying goodbye to him at the airport and the mother looks to be white or Latina, so it's also nice to see that this could be a story about a mixed child.
Caroline Binch is probably most well-known for illustrating the Amazing Grace books. She also illustrated the Caribbean book of rhymes Down by the River which I reviewed here.