I recommend Barbados for families, couples, and solo travelers alike. My family has owned a house here for 60+ years, yet we never tire of coming. Unlike some other islands that are pretty much just artificial resort culture replicating U.S. resorts, Barbados is a real country with a distinctive flavor combining British, Canadian/U.S., and Afro-Caribbean cultures. Barbados has a rich, vibrant history like Puerto Rico, and has superb, well-maintained historic sites, as well as ecotourism, nature preserves, animal attractions, and much more! The food is incredible too!

It is also worth noting that because Barbados is so far to the south and east in the island chain, it is out of the path of most hurricanes, and it also has no malaria or wild snake population. It is a well-educated, prosperous country with relatively low crime rates, and virtually no violent crime. (for the worry warts)

Barbados is accessible easily on AA from JFK, MIA (2x daily), DFW, and SJU.

Let me know if you decide to visit the island, and I will PM you more info!