The Joys & Challenges of Traveling With an Unprepared Friend

By

Andreas Jones

Hey! I’m Andreas Jones and I am the founder of KindaFrugal.com. I’m passionate about all things personal finance, side hustles, making extra money, and lifestyle businesses. I have been featured in major publications such as Forbes, Entrepreneur On Fire, Lifehack.org, Influencive and Goalcast.

| Published on May 12, 2024

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Traveling With an Unprepared Friend can be an adventure in itself. Bill Bryson’s “A Walk in the Woods” isn’t just a book; it’s a cautionary tale for anyone venturing out with an unprepared friend like Stephen Katz. Whether it’s a lack of gear, money woes, or just a knack for draining the fun out of any journey, traveling with a Katz-like companion can turn into quite the saga. After reading this tale, we were inspired to turn to the internet in search of other tips for handling misadventures with friends. Read on for the 10 best tips we took away from our research.

Loan What You Can Afford

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A good rule for traveling with a broke companion is only lending them an amount of cash you will be willing to waive — chances are you won’t see it again. One story involves a travel companion putting his friend on the spot by asking for a holiday money loan after arriving at their destination. The storyteller refused, saying he knew the money would be gone forever and didn’t want to lose a friendship. His travel buddy wasn’t pleased.

Kindness Goes a Long Way

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A group of friends treated their unemployed friend to an all-inclusive Cuba holiday, though he refused their invite on excursions, as he was already grateful enough. Thankfully, the kindness they showed and his guilt at missing the excursions motivated him to make a positive change. Once he returned to America, he turned his life around and started a successful career.

No Pay, No Play

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To keep the peace, some people have a no-nonsense approach to friends who come unprepared on vacation. Tough love is sometimes necessary, and hopefully, it will spark the friend into organizing their finances better. However, some friends genuinely need help or may be going through a tough time — it all depends on who they are.

What Goes Around

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True friends understand each other well enough to know when one of the pack needs lifting. Some friends would do the same for you, so why not spread the love if you can afford it? That is what friendship is all about. The lesson here may be to avoid traveling with lesser-acquainted colleagues.

Choose a Suitable Location

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If you know your travel friend is experiencing financial hardship, maybe a VIP experience in Ibiza is off the cards. If there is a financial rift between the two parties, why not lower your budget instead of putting pressure on theirs? A long weekend at a national park can be more rewarding than an all-expenses Cabo journey.

No Hard Feelings

Two men traveling
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A wealthy American professional moved to Europe, inviting his best friend, who left behind his entire life in the States, to join him. He has no money, but the poster doesn’t care, stating that his company means more than any money, so he happily funds their adventures as he looks for work. Paying a little extra to have your wingman join you for your dream adventure; can you even put a price on that?

Sometimes, You Are the Stephen Katz

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Spare a thought for the friend who booked the trip but faced an unexpected or sudden financial hardship — maybe they lost their job, had to pay for funeral costs, or their car was totaled. No matter how graciously your companions help you with money abroad, it can’t feel empowering.

The Joneses

Annoyed couple travelers
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A married man recalls how he and his wife tried to keep up with his wealthy friends while she was finishing her degree, and he was a new graduate. The friends were all established, affluent professionals who invited the couple to Tuscany one summer. The commenter explains how they put themselves into financial trouble, though they opened their eyes to the lifestyle they wanted — which, sadly, didn’t include five-star hotels in Florence.

You Didn’t Give Me a Chance

Two female friends comforting her upset friend
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One story involves a needy friend being shady about how much money they had saved before the trip began, then revealing how broke they were once they arrived. Subsequently, she complained when the group chose mid-priced restaurants, joined on excursions but sulked about the price, and complained that nobody gave her enough time to save up for the trip — six months.

Be Upfront

Female Friends Having Fun Together
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If a friend suggests going away somewhere, maybe the best option is to be upfront about everything. If you feel they are not at their financial best, a better idea would be to suggest a cheaper or shorter adventure somewhere — an overnight mountain biking tour, a staycation in your city, or visiting a mutual friend’s place for a night instead. Source: Reddit.

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