Where ever did you find an airfare for $19? I would call everyone I knew and tell them about it. Even when we went to Cayman in 1969 the airfare from Chicago was $125.
I agree about a condo. We have traveled with our children starting when they were 1 and 4 and our grandchildren when they were 1 and 4 and have loved staying in a condo–space is great and having a kitchen is great too. Our kids became friends with kids their age over the years–we have since gone to their weddings. It’s kind of like camp friends–only these are our Cayman friends. There are usually quite a few kids at condo complexes especially during the holidays. But I imagine that there are quite a few kids who are not school ages at other times.