Hoping to get past the exotic holiday resort image and explore the realities of island life, Sir Trevor McDonald travels to the Caribbean to meet its residents and experience its many contrasts. Along his way he meets his Cuban news-reading counterpart Mariuska, takes a tour of the British Virgin Islands with Richard Branson, travels to his birthplace, Trinidad, visits David Copperfield's opulent resort--the most expensive in the Bahamas, talks to jailed British drug mules in Jamaica, and finds out why Barbados has become a luxury haven for the rich and famous.