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If you trust your travel companions to pull their weight financially, another option is to trade off paying the bills. Pressner says this works especially well with couples. "With certain couples that I travel with, sometimes I'll pick up a bill or just handle the rental car because I know that next time they'll be getting the dinner," Pressner says. "As individuals, I think it's important to keep track of what you're spending. One person does tend to be more generous, and you don't want that person to feel taken advantage of."