We have been cruising for the past 20 years, mostly with Princess. The last few years we have taken advantage of the 3 for Free promotion. However since we are now retired, we can and have booked longer cruises. It also appears that these cruises can go down in price substantially after last payment date. We are in a position to do last minute bookings.

Do we book with a promotion, following the prices and then if it goes down substantially just cancel and rebook? The cruise line generally will not honor lower price unless you cancel and rebook, which eliminates the perks of any promotion you signed up with. Or do we just wait and take our chances on cabin availability and book last minute? At one time, we felt like we were in a better position booking early, But now upgrades are pretty much a thing of the past, replaced by upsells, which if you take advantage of an upsell, you pay more not only for your cruise, but your travel insurance as well.

Does anyone have a rule of thumb as to how bookings or when bookings are best made early or late? Any thoughts appreciated!