I know that airlines schedules come out around 11 months in advance and therefore that is when you should start looking for reward availability. However, seeing as I have never booked any reward stay, when does one start looking at booking reward nights at hotels? Does it vary by program? I ask because I am looking at going to Hong Kong and the Maldives in June of 2014. The plan is to use 4 free Hyatt nights from the Chase Hyatt credit card (2 for me and 2 for my wife), Hilton points to book 4 nights the Conrad Maldives using the Axon award amounts, and then 4 nights at the Courtyard Marriott in Hong Kong from the 4 free nights from the Chase Marriott reward visa. This all came about because I need to use the free nights within a year of getting them and if I get the Hilton Surpass from Amex for Gold status, that lasts for a year as well. I guess I could still get Axon awards with Silver but it would be nice to have Gold status while actually on the trip (I don't travel enough to actually achieve it the real way). Since two of these are Visas, could I apply for all (Marriott and Hyatt) of those in June/July. Would applying for one of them in September/October be too late? Does it matter that I plan on doing the Ink and United Mileage Plus in December/January and then the Bank of American/Bank of Hawaii Visas in March/April? One other question is that for the Park Hyatt Maldives and the Courtyard Marriott Hong Kong, would the two free nights for me and the two free nights for my wife be separate reservations? Would we have to check out and then check in to a new room? Or does that all depend on the availability for the hotel? Thanks for the help!