When do I pay for travel insurance? Dane April 20, 2018 20:11 Updated Follow Travel insurance must be added to your vacation package at the time of booking your reservation. Related articles When does interest start to accrue? What kind of travel can I buy with UpLift Pay Monthly? Can I use gift cards to make a loan payment? Can I negotiate the rate or my loan terms? Comments 0 comments Please sign in to leave a comment.