Cayman - food is great, people are incredibly warm and friendly, it is very safe and the water sports (for diving, snorkeling, etc.) are fantastic with many options.

Very easy to get there - can fly through Charlotte, Atlanta, Miami, NY, Dallas - and seasonally there is a direct flight from DC.

Just checking and flights under $500. Would you do Aruba or Cayman. Costs are about same. Flight better options to Cayman though. Kids tweens and love beach