My thoughts, worth nothing but here goes.
Two four night cruises will get you to a new tier quicker so that's a plus. Is that $3100 each or for both? I am going to assume each but if it is for both, jump on that quick.
the Destiny is a great price for 5 nights however with that being said, on a 5 night pretty much the ship is really the main event. You mentioned two ports but you will mostly be on the ship. The theme of it doesn't make me want to rush out to sail her but with that price, I would do it.
The Magic was my first sailing and I love how quaint she is. Loved sailing her and hope to again sometime in the future.
While I myself am dying to do another sailing with anyone we find ourselves doing more Caribbean vacations. We did the DR in December and are going to do it again in nine days. All inclusive is always a great way to go and you would have a blast in Mexico but would you miss not be on a cruise? How would you feel? Sort that and you will know which way to go.
My niece and her family are on the Wish right now and I'm so very jealous. It has taken me to the
DCL page and looking at pricing myself. I want to get back on the Treasure. That ship fascinated me. The bars, the Moana show, the Coco dinning room, everything about that ship blew me away and I did not think I would enjoy it at all. Shows what we know, lol.
What ever you decide have a great vacation. Pick what will make you happy. This winter has been so harsh. Something to look forward to brings a bit of sunshine into our lives, doesn't it?