Right now I have a ton of stuff on my plate that im saving for. As soon as the blonde gets back to me this week, my current savings is depleted for the trip to Ecuador, and then after that I have a wedding in Jamaica to go to that i refuse to miss! lol
Somewhere in between that all, I would like to plan a huge family vacation, involving, like you mentioned, a cruise to one of those places.
Now as someone else said here, Bermuda is the best destination. But that's not the Caribbean.
I've done the cruise thing, and personally imo I like it better when you just fly to where you want to go and just chill there. More relaxing, and NO crowds on some of these islands.
We wouldn't be going on this cruise except for the wedding.
We were actually booked for Maui in May but had to cancel because my wifes annual sales meeting was scheduled in the middle of that week. That was a major friggin bummer. Hawaii is amazing.