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This is arguably the most ingenious way to travel for free. Plan a trip for a group of friends or family, then reach out to various travel operators and barter a deal. Many companies (especially startups) will cover your costs if you position yourself as the trip leader. For example, YMT Vacations will pay for your vacation if you can enlist 12 people to take a trip with them. So long as eight members of your group book their f light through YMT, they’ll even cover your airfare.