Essentially, NEVER pay for major travel expenses with a debit card if you have a CC you can use. Meals and things like cab fares are OK, but not room charges, rental cars or air/cruise tickets. You need the dispute resolution service and the warranty that a CC provides. Out-of-town shopping should also be done on a CC if there is any possibility that the item might break or get damaged in transit.
Also, when using a debit for rental cars, some agencies will sometimes put a "reserve" against your account for more than the price of the rental; if you don't keep a lot of money in the account, you could discover that your entire account balance is locked-down.
If I want to pay for an entire trip up-front, I just move the money to my CC account the day before I leave for my trip. That way, the money to cover the expenses is already in the account, and I will not have to deal with paying the bill when I get home.