By Aditi Shrikant
Day to day, it can be relatively easy to navigate a friendship with a person who earns a lot more money than you. But on vacation, it’s much more challenging to ignore financial disparities.
For her 50th birthday next year, Sarah Kopit wanted to plan a trip with 10 of her childhood friends.
Kopit, the editor-in-chief of travel-industry news site Skift, knew it was going to be a daunting task – not only because wrangling almost a dozen people with different schedules is singularly challenging, but also because she was acutely aware of how different everyone’s financial situations were.
“It’s 10 people who grew up together but went off and did very different things,” Kopit said. “A lot of different income brackets, from stay-at-home moms to doctors and lawyers.”
Eventually, they agreed that an all-inclusive resort in Mexico would be the easiest option for a group of their size with varying incomes.
“When we floated the idea of an all-inclusive [trip], so money [while you’re at the destination] isn’t something that’s even a part of the conversation, everyone was like, ‘Yes, let’s do that,’” she said.
But the decision took months to reach, Kopit said. Planning a trip that every person was excited to go on and could comfortably afford was time-consuming and, at times, awkward.
Day to day, it can be relatively easy to navigate a friendship with a person who earns way more money than you. On vacation, though, it’s almost impossible to ignore financial disparities.
If you’re planning a trip with a friend who makes more money than you, it’s important to address that reality beforehand. Doing so can help minimize friction on the vacation – and keep you from spending money you don’t have just to keep up with their expensive taste.
Friendships depend on equality
Even with good friends, talking about money can be difficult. That may be because salary disparities can stir up feelings of resentment, especially among young people: 29% of Americans say they’ve been jealous of a friend who earns more money than they do, according to an exclusive YouGov poll conducted for MarketWatch. For respondents ages 18 to 29, that number goes up to 35%.
Aida Mollenkamp, founder of the boutique travel agency Salt & Wind, has planned dozens of trips for friend groups who don’t even realize they are in different income brackets.
“The thing that tends to happen is that at home, the person with more money thinks the other person has as much money as them because they think, ‘We went to this splurge meal together,’ and they don’t realize it was an actual splurge for the other person,” she said.
Friendships, more so than romantic partnerships, depend on all things being equal, said financial therapist Amanda Clayman. Footing the bill for a fancy meal with your significant other is more commonplace than doing so for a friend.
“It’s important that the relationship structure of a friendship is based on mutuality,” she said. “There is an overall balance in the relationship that isn’t hierarchical.”
Financially, it’s also much more feasible to plan for one stretch dinner than for a whole week’s worth of them.
“It’s easier when we can take these little experiences a la carte,” Clayman said. “I pick up lunch and then you pick up lunch. We have a little bit of architecture to that individual financial event.”
If you’re traveling with someone whose budget wildly exceeds yours, you need to have a straightforward conversation about what your limitations are. Then you can move forward with planning a vacation where both parties feel understood.
Have a detailed conversation about budgets
Do not expect your high-earning friend to bring this up on their own, Clayman said. “One of the first things people buy with affluence is the ability to avoid friction,” she said.
You’ll probably have to be the one to ask about the budget for the trip. Before doing so, be sure you know exactly what dollar amount you’re willing to spend.
“Know what your number is so when you go into this conversation with a friend, you’re not going in thinking, ‘What is the most amount of their number or their budget that I can afford?’” she said.
This shouldn’t be a one-time discussion. The more you both research the destination, the more you’ll want to add to the itinerary. And while it’s easy to get excited and add a pricey excursion or upscale meal to the schedule, you need to be cognizant of how this will increase the budget.
If your friend uses vague language like “This is affordable,” be sure to ask clarifying questions, Clayman added: “What’s affordable to one person is a treat to another.”
Many friends also make the mistake of only talking about the big agenda items like museums, tours and shows, Mollenkamp said. But oftentimes what leads to friction when traveling are the small, ingrained habits that we usually don’t confront at home.
“Ask your friend about their travel style,” Mollenkamp said. “How much jet lag do you usually have? What’s your morning routine like? Do you get up and go, or do you get going midday? What time do you eat meals?”
If your friend wants to have brunch every day but you prefer to just grab a sandwich on the go, that’s important information to know before going on a trip together.
Tips for saving on expensive travel
There are some ways to make traveling with your high-flying friend less daunting.
First, look into which accommodations and flights might be covered by credit-card points, said Nick Ewen, senior editorial director at the Points Guy.
“If someone is points rich and cash poor, one of the things they could say is, ‘I’ll use my points to get our flights and hotels, and you pay for all the incidentals,’” Ewen said. “That can level the playing field.”
Once you’re at the destination, it’s easy to get caught up in what your friend or the group wants to do. But remember, you can always opt out of experiences that don’t fit into your budget.
“It’s OK to not do everything together,” Ewen said. “Being on the trip together is what’s important. If someone wants to do a four-hour, $800 spa package, you can spend four hours going to read a book by the pool.”
If you want to minimize the number of unexpected expenses that might arise, you can opt for an all-inclusive resort, as Kopit and her friends did. Still, that doesn’t mean that everyone will get 100% of what they want. There was “a little bit of grumbling” about some of the shortcomings that tend to accompany resorts, Kopit said.
“From some of the foodies in the group, there was a bit of consternation about going to an all-inclusive and the food not being a Michelin-star experience,” Kopit said. “But the idea is: The beaches are gorgeous, the drinks are tasty, and the food – it’s good enough.”
If you’re just starting out on your money or career journey and have questions about how to navigate your finances, we want to hear from you. Write to Dollar Signs, MarketWatch’s new advice column, at dollarsigns@marketwatch.com.
-Aditi Shrikant
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07-18-25 1431ET
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