My problem is that I like to travel, usually far from home, and like to do 3-4 trips like this per year spaced throughout the year so I don't lose my mind at work. Thankfully I have more vacation time than the average American employee (I have 4-5 weeks annually to play with) and I try to travel over holidays to minimize PTO, but that still leaves me often with only 5 days, plus any weekends it coincides with.

For me Thanksgiving is the best week to travel over. Costs 3 days of PTO for a 9 day vacation. Being Canadian, my family could care less about Thanksgiving, so they're fine with the Christmas get together.