In short, if you are spending $300K+ a year on credit cards, you should be able to get free First/Business class airfare and Hotel once a year to Europe and Hawaii, without too much effort. You should be able to easily earn 200-300K miles or points based purely on spend and another 200-300K miles or points for a few good bonus offers each year (100K credit card deals, Fidelity promotions, Hotel or Airline giveaways, etc.).

In order to determine how to do that, we would need to know what airport is closest to you and where you go and stay in Europe and Hawaii. Based on that, it is easier to suggest which airline and hotel programs would work best for your situation.

Ike
p.s. Welcome to FlyerTalk!