OK, I think I have made some progress.
Alaskan Airlines flights 35k each x 6 people...210k points....need help with this part.
Hilton Grand Wailea x 5 nights x 2 rooms. room 1 380k hilton points. room 2 UR portal/ 159,760 points.
Westin Kaanapali x 6 nights x 2rooms. Room 1 104k SPG points. Room 2 104k SPG points (purchase 30k)
*(I'd rather do Aulani at 381k URs but i think i need those for flights?)
Hertz car rental on hertz points.
Alright...I even got all this lined up around the flights. Here is the kicker...how in the world do I buy the alaskan flights with alaskan points.
Here is my current stash (pending points):
Hilton 413k (earn more every week)
SPG 59,706 (55k pending. Can buy 30k x2)
UR 361,379 (116,523 pending)
Did I organize it to make best use of points? Should I change something? How to do make my URs into alaska miles...need 17,500 each way for 6 people.
ETA: this completely wipes out my entire stash.


do I really want to go to hawaii? all you young churners out there...remember when family planning that hotel rooms are made for 4.