Barbados:
Barbados is like a small tropical version of England, except that most of the rich people are white and most of the poor people are black. However, the education system is reputed to be the best in the Caribbean, and upward mobility is possible for the poor. Also, the health system is accessible to all residents.
Most people go to Barbados for the beaches and the reef, as well as the sailing. It's not cheap, though, so take lots of money. Bridgetown is the capital city, and it boasts a parliament that's the third oldest in the British Commonwealth, dating from 1639. Barbados is sunnier and drier than other Caribbean islands, but it is also vulnerable to hurricanes.