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My friend's TA asks her Princess rep. for the upgrades for her clients.  They are Captain's Circle members, but I don't think that makes much difference.  Their TA has contacts and has gotten them some fantastic upgrades for free.


Another way - go with a "guarantee" instead of an assigned cabin. 


Another way - pay for it like most people do!


You could pay off your cruise very early.  From what I've seen, this helps.  Also, if you make a large payment just after booking, it might help.


Or, just hope you're lucky.  In other words, it's the luck of the draw most of the time.


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