Originally Posted by
svenskaflicka
Oh, hindsight. We have thought the same thing soooo many times. I bet we have dropped at least $100,000+ while on the islands. We have been there fifteen times since 2000. When we first started going, we used to pay $247 at the Westin Maui or Royal Hawaiian for our room per night and they would always give us a great upgrade. Now, there are no more great deals and on average we spend $500-600 per night. We no longer go to the Westin or Royal Hawaiian. It's sad because a vacation should be what you want it to be. You shouldn't have to settle for a dumpy room because the prices are so high.
For someone spending this kind of money, you'd be better off buying a timeshare. I know you don't buy them for an investment, but I've already gotten my money's worth from the points I own with Hilton, so my 3+ weeks a year, including 2 in Hawaii, only cost me the maintenance fee, which is about $600. (I usually book a studio off season to get that many nights with my small amount of points.)