you have gotten some really, really good advise from my fellow cruisemates ( as usual). I totally agree about going to talk to a local travel agent, ask for their cruise specialist. Just sit down and talk, tell them what you have told us. I think that an Eastern route would be good for you and your daughter, would Ft. Lauderdale, FL work for you as a cruise port? I also think that Royal Caribbean cruise lines would be a good fit for you and your daughter, for me personally i would look into the Freedom class of ships, i think that the larger Oasis and Allure might be a bit overwhelming for you, Another really good option would be the Grand Class ships of Princess, these are big ships but not huge ships. Dont rule out a cruise just because it stops in Jamaica, Jamaica is a gorgeous island that unfortunately has a bad reputation, there are so many reputable safe tour options to consider in Jamaica.