Just found the boards, and didn't realize what I was missing . . .lots of great information on here. I'd like to get some thoughts as I start planning my honeymoon. Here are some of the key details:

* Currently a gold member with 290K points - Need 5 more stays to get to Diamond which should happen in January. Currently spend around $300/week at Hilton locations.

* I just got engaged and looking to book a honeymoon in October 08. Location is open, but would probably stay within 10 hour plane ride of Washington DC area (only going for one week so don't want to spend too much time getting there). Currently looking at Cabo and Hawaii, but I'm definitely open to other options. Beach is not a requirement, just want a relaxing place to visit.


Questions:
1) Any good suggestions on places to go?

2) How far in advance should I try to book an award stay? I'm assuming that it would be better to wait until I'm actually a diamond member? Do you get a better room or any other perks for being diamond on an award stay?

3) Can I get an upgraded room by mentioning it will be my honeymoon, or can I pay to upgrade (either in points or $$)?

4) Anything else I should know about?

Thanks in advance.