Oh, for heaven's sake, tell her. Why are you keeping it a surprise? Don't add more stress to her life. Besides, if you tell her, she can help collect points.

I agree with the others who are saying don't try to do Europe and the Maldives. You don't say when the wedding is (just in about two years), at least that I saw. If you're in Grand Rapids, you'll want to go to the Maldives in the winter. And you really don't want to go to Europe in the winter (tho it could be a lot warmer than Grand Rapids). Trying to pack for two really different climates will be another stressor.

Singapore airlines flies to Male, so if you book an award flight on SQ, you can probably get all the way to MLE for the same miles as to SIN (tho I haven't looked, so that could change).

I've stayed at the Conrad Rangali in the Maldives three times, with a fourth visit for early next year. it may not be as nice as the Hyatt, but it may be easier to accumulate free nights. The Reserve card gives you two free weekend nights as a sign up bonus. Beware, they will expire in a year, so you don't want to get the credit card more than a year out. The thing with Hilton is that you also can collect miles with the Amex card. This you might begin working on as soon as possible. 5 nights would be 475k points, but if you have Gold status which you would get with the Reserve credit card, then it's 380k points. (These can't be aggregated between your account and your fiancee's). So, get the card when there is a high sign up bonus and try to collect the remainder of the points this year so you can make your reservation as soon as you have your free nights from the Reserve card.

So, here's the plan: 5 nights on points (380k-50k sign up--hopefully more leaves 330k points which is a lot)
2 weekend nights at the beginning from the signup on the Reserve card that you get.
2 weekend nights at the end from the signup bonus on the Reserve card that your fiancee gets. That's 9 nights in a place that runs $1000 a night.

Unfortunately the ability to sign up over and over again for bonuses has ended, so your work is going to be a lot harder.

I like to overnight in MLE before going to the resort so I maximize my time at the resort.

Best wishes!
(Oh, for the record on the comment about telling your fiancee, I'm female)