I'm hoping to go on a nice vacation with my wife for our 10 year anniversary next summer/fall. We've managed to accumulate a good amount of miles and points over the last few years and I'm trying to figure out strategies for using them effectively for the trip. (We've hardly made any redemptions over the last few years except for a few random domestic hotel stays and flights.) We're thinking about Italy for our trip, probably a mix of Amalfi Coast-like areas and a city or two. We live in Los Angeles and would have about 10 days total, including travel time. Our miles and points situation looks like this: American: ~600,000 miles jointly (400k/200k) Delta: ~85,000 (Nothing else over 50k on any other airline) Hilton: ~79,000 Hyatt: ~37,000 (plus two free night awards) Starwood: ~250,000 Chase UR: ~180,000 Amex MR: ~260,000 I realize this is a fat mess of points and transfer options are abundant, which is what is making things more complicated for me. It would be great if the trip was fully funded by points for our flights and hotel stays. And we'd prefer top notch accommodations. Any thoughts as to how I should be thinking about this?