Originally Posted by Mile-a-holic

So I sympathize: we couldn't afford a honeymoon and our first few anniversaries were within driving distance, so I really applaud your travel hacking approach. But a few questions:

1) Are you sure she'd agree that Hawaii is the best use of 130k miles? Or, would she prefer a different destination?
2) If you're carrying balances on other cards, will it mean you'll be stressed about other costs while in Hawaii? Would she/you rather go in a year when you can perhaps afford to splurge on a helicopter tour, or hop between the islands, buy a special souvenir, etc?

Is she the type that enjoys planning trips? Would she love spending two or three nights in a very upscale hotel (on points of course!) nearby for anniversary two, with the present being "let's plan a trip together anywhere for next year using miles and points?"

It's just food for thought - Hawaii is spectacular, and can be done relatively inexpensively if you rent a house or condo surprisingly. But if you're staying at a hotel, you want to be able to enjoy the pool and not be worried about the cost of ordering a drink or food, or skip things that you really want to do (whale watches, etc).