I've churned our way through 4 Delta cards (Gold, Gold Business, both x 2), 5 American cards (Citi Platinum, Citi Platinum Business, both x 2, and Barclay Aviator), 2 SPG cards (Amex x 2), 4 Hilton cards (Citi x 2 before they switched, AmEx x 2), CSP, Capital One Venture Rewards, Chase United, and Barclay Miles N' More (Lufthansa) - I think that's it... ;) We've still got the Platinum Delta cards (x 4) that we can burn through, plus another Aviator, CSR x 2, CSP (if I can ever get myself below 5/24!), and another Capital One Venture before I have to start getting creative! We almost always each sign up for the same card to double the bonuses we get! So far have booked 3 trips to St. Croix on miles (first two were just the wife and I, this next one is us, the two kids, and my MIL) and we STILL have nearly 400,000 airline miles and almost 600,000 hotel points left to burn. We started first with Hilton around 7-8 years ago, then gradually moved into the other programs. Needless to say, we haven't paid for a hotel room for a long time! Congrats on the Hawaii trip, that is definitely on the radar for us in the future!