I am taking my Dad on the Grand Princess on October 29 from Venice to Rome. Right now we have a mini-suite. Because of some favorable financial circumstances, I am thinking of making it so we each have our own room or we upgrade to a suite. I checked availability and there are a fair number of both still available.
Is there a certain time when it will be significantly more advantageous to discuss this with Princess. I am happy to pay extra, but don't want to throw money away if the prices will drop or if we can get an upsell or upgrade at greatly reduced cost.
There is never no guarantee that the cruise line will make such offers. The cruise is still thirty days away. Ask yourself "If I stay in the mini-suite and don't get offered an upgrade, will I be happy with the mini-suite, or will I be regretting I didn't pay for an upgrade?"
I am amazed there are still suites available 30 days from sailing. If you want a second cabin or a suite I would book it immediately. Upgrades are extremely rare and usually only within the type of cabin of the original booking; the only instances of upselling of which I have heard on Princess were simply offering a better cabin at its regular fare--they were not bargains.
And congratulations on your good fortune, and what a wonderful thing to do for you Dad.
If they still have 10 unsold suites, you should call Princess right away; you just might be able to negotiate a good deal. Even if they don't offer you a good deal, a suite would be less than two mini-suites. You would have to pay the single occupancy supplement if you get two cabins.