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Just a reminder to first decide where you want to go, don't let the point redemptions decide it for you (e.g. Australia probably won't be the best place to visit since it'll be scorching)
Leverage 5th night free whenever possible, which is really just in large cities or any place days trip options are plentiful.
Transfer SPG points to Alaska to book an award on Cathay or JAL. You get a free stopover even on a one way and business is only 50k miles (I think for both, JAL might be 60k). Easy way to do HK/Tokyo and another Asian country.
Keep in mind you get 25k Alaska miles for every 20k SPG
I really like the Marriott hotel + air packages. 90K SPG for 132K united miles and 7 nights at a reasonable Marriott, enough to finance a week-long business class round trip to Europe.
That's a good chunk of points. Probably 3.5k cash worth
Sheratons help maximize. Great value internationally and great breakfast and lounge access if platinum
Hire a points hacker! You pick the location and they'll figure it out based on your status and points
Bali and Thailand would be a good start in winter. Maybe do a safari in South Africa or Kenya "on the way" there or home. Having done a safari in the Sabi Sands area of NE South Africa I highly recommend it to everyone. Can't use SPG points for a safari location but you can use them in Indonesia and Thailand.
@P1 can I ask what a safari would cost roughly for 2?
Figure $600-900 for a higher end one per night though the weaker S African economy may be pushing that cost down a bit due to the Rand being weak against the dollar. Most lodges include a sunrise and sunset game drive. It won't be cheap, and you won't be using hotel points, but it is very worth it. I did three days last I was there, might consider four were I to do it again.