Good luck, OP in reaching your goal. You've received some great advice on this thread from all the posters.

I agree with the poster that asked how your wife feels about this trip. Mr. love2ft and I are finally going to Hawaii too...for our 10th anniversary and I'm okay with that. It may have taken us longer to get there, but now we don't have to worry about going into debt for a vacation nor do we have to pass up on any experiences/shopping while we're on our trip. Staycations are great when you're with the right person!

As you're new to the "game", make sure you pay down your debt as others have advised and avoid getting into new debt while you chase the miles/points. It's very easy to charge things "for the points", but your credit is more important than anything else!