We did a cruise out of New Orleans in March, got our flight info 37 days before departure. We have a cruise booked in August out of Sweden and go our flights 75 days before departure. We had a day deviation before the cruise in both cases.
I am happy with the flights I got for both, and I they were the flights that I would have likely booked myself if I was paying directly.
For Winnipeg to New Orleans I had two connections (Toronto and Atlanta) but that was about as good as could be done. On our way back, we had only one connection (Toronto). The layover times were 2 hours or less.
For our Sweden trip, we have two connections on the way again (Montreal and Copenhagen), and then one on the way back (Toronto (Our cruise finishes in Copenhagen). Again, all the layovers are fairly minimal, but have enough time for me to feel comfortable with the flights.