Hawaii on Points
 

My wife is wanting to go to Hawaii in September and I'd like to book the trip with points if possible. We'd like to stay at a high end resort on Maui.

Through my business I have around $100k in monthly credit card spending, so it should be relatively easy to open a card and earn enough points, I'd just like to hear everyone's thoughts on the best way to go about this.

I have never been to Hawaii before if that helps sway any advice.

The first thing I'd do is check if there is award availability on AA, United, Hawaiian, etc. Depending on where you find availability I'd apply for that cc.

For hotels it'll be a bit easier. Maui has the Hyatt, Andaz, Fairmont and Westin. Depending on where you'd like to stay apply for that cc. The Hyatt cc will get you 2 free nights anywhere and if you and your wife both get a card that'll get you 4 free nights. I've heard the Andaz is difficult to get with the free nights, but you should be fine with the Hyatt. The Fairmont will get you 2 free nights as well.

Getting award space for the air this late will be tough.

OP, what did you decide to do?

I think he'll be alright. September is the least busiest month of the year for Hawaii.