There has been a book that has been mentioned on several blogs that I follow. I finally got a chance to read "An Embarrassment of Mangoes: A Caribbean Interlude" by Ann Vanderhoof.
The book chronicles the real-life two-year trip of Ann (a publisher) and her husband as they put their careers on hold and sail from Canada thru the Caribbean and back and how that trip changed their perspective on a great many things. You are introduced not just to the locales that they visit, but the people they meet along the way and the challenges of making a lifestyle change like this. At the end of each chapter you are also introduced to some of the local cuisine they encounter in the form of recipes.
It is not the typical travel book and is a very good read for anyone that is considering this sort of lifestyle.