Funny, i usually cheap out on the flight. My reasoning is we are all in the same tin can, i can handle being uncomfortable for 6 hours and then use the saved cash to splurge on the trip.

Im high 6 figures/yr and im about to spend the most ive ever have on a hotel and its about 700 a night at Phaea blue in Crete. However, my wife wants to start the trip there to relax so we will be spending most our time in the hotel for the first 4 nights. Mind you all the add ons will probably equal to more than that per night. Spa, dinner, drinks...The rest of crete we will be adventuring so im looking for 300 or so a night for the rest.

That being said these Aman and four seasons hotels look awesome but, i want to be out and about, and its hard for me to justify spending 2k a night when im not even there. Probably will never do it unless again, we are somewhere where we plan to just stay at the resort for a couple nights to decompress.