Let’s imagine for a moment that you’re looking at the bill in a hotel restaurant. It’s one of multiple times you’ve dined out this week, and beads of sweat start collecting on your brow as you panic over how many more expensive outings might be coming… if your friends keep insisting on them.
This is one of the potential perils of the vacation with friends. It always sounds fun, but there is work involved to make sure these trips don’t turn into nightmare money sponges that make people feel like they are in a season of “The White Lotus”.
“One of the big things where a lot of the kind of strife comes from is the money,” on these vacations, said Mark Wolters of the Wolters World Travel and Culture YouTube channel, also an associate professor of Business Administration at the University of Illinois Gies College of Business. He joined WBBM Newsradio’s Rob Hart on the Noon Business Hour this week.
Wolters said its important to iron out the economic details before heading out on an adventure with buddies. A misalignment – such as one friend expecting five-star dinners and another content with whipping up quick grocery store eats – could strain wallets and relationships.
“If you don't feel comfortable talking about the money thing, then it might not be [someone] you want travel with, because that’s going be the biggest issue overall,” Wolters told Hart.
Honest communication can help with other aspects of friend vacations as well. If one part of the friend group would rather zip-line while the other lounges on the beach, it’s good to have a conversation about that so everyone gets to do what they want and resentment doesn’t set in.
Jumping right in to a two-week Caribbean vacation might not be the best idea for friends that haven’t travelled together before, Wolters said. He suggested starting small with a weekend tip to a nearby vacation spot.
That type of test might reveal that your best friends aren’t a vacation match made in heaven. Wolters said it won’t be the end of the world.
“I have friends of mine. We’re best friends, and… I will never travel them again, and we’re cool with that because we don’t travel very well together,” he said.




