You do not say when your cruise leaves, but if it leave late afternoon of 6/14, I think the flight you are looking at is "iffy". A cross country flight with a change can be delayed and you must allow a few hours to get bags and travel to ship.

If you fllight leaves 6/15, you could fly to Orlando on 6/14 on Award, stay overnight, and get a one way rental car to Tampa. Have to think of various options.

And remember, you can adjust the return to different airports than the outbound in case you can get Tampa to PDX for the return.