Traveling with High Maintenance Friends – Episode 12

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Traveling with High Maintenance Friends: Tips and Stories

On this episode of Bon Voyage Besties, join Rachel and Rosa as they navigate the complexities of traveling with high maintenance friends, sharing personal stories, red flags, and practical advice. Whether you’re an over-planer or a casual traveler, learn how to handle different travel personalities and ensure everyone’s trip is enjoyable.

Key Takeaways

• What does “high maintenance” really mean in the context of travel?
• Types of high maintenance behaviors, from rigid itineraries to picky eating and constant complaining
• How to identify red flags in friends before traveling together
• The importance of planning and setting budget expectations upfront
• How cultural differences impact travel behavior and reactions
• Tips on handling disagreements over costs, activities, and preferences
• The value of having space and flexibility during trips
• Strategies for difficult travel companions and declining invitations gracefully
• The significance of honest communication and shared responsibilities
• Personal stories of travel mishaps and lessons learned

Remember: Clear communication, flexibility, and understanding your own limits are keys to a happy travel experience with friends.

Listen on APPLE PODCASTS | SPOTIFY | YOUTUBE

Traveling With High Maintenance Friends

Let’s be real, traveling with high maintenance friends is something almost every traveler has dealt with at least once. And before you start mentally scrolling through your contact list, consider this: if you’re not sure who the high maintenance one in your group is, it miiiiiiiight be you. We’ve all got our quirks on the road, and sometimes the most self-aware thing you can do is own them.

On a recent episode of Bon Voyage Besties, Rachel and Rosa sat down to dish out honest, been-there advice on navigating the full spectrum of travel companion chaos. Here’s what they had to say.

What Does “High Maintenance” Even Mean When You Travel?

In everyday life, high maintenance can mean a lot of things. But in travel, it tends to fall into a few very recognizable categories.

There’s the over-planner, the one who has a color-coded spreadsheet before the luggage is even packed. (Rachel fully admits to being this person, complete with a Google Doc itinerary that once prompted her Barcelona travel companion to ask why there was a spreadsheet for a week-long vacation.)

Then there’s the picky eater who won’t sit down anywhere without cross-referencing three review apps first, the constant complainer who narrates every inconvenience from a delayed bus to a slow elevator, and the luxury loyalist who genuinely cannot fathom sleeping somewhere without a spa, a king bed, and a balcony view.

Rosa adds another category worth mentioning: the person who only goes somewhere because it looks good on Instagram, without actually caring whether the food is good or the experience is worth the price tag. She has firsthand evidence of this: a Miami beach brunch that cost $150 for waffles and eggs because a friend had to have the Instagrammable view.

The Red Flags You Can Spot Before You Even Book the Flights

Here’s the most valuable piece of advice when it comes to traveling with high maintenance friends: the warning signs are almost always there before you go. Watch how your friends behave at home. If someone is a constant complainer at a casual dinner, they’re going to be a constant complainer when the train is late in Rome. If someone is snippy with the wait staff at a local restaurant, that behavior doesn’t take a vacation just because you do.

The financial dynamic is another big one. You don’t have to be earning the same salary as your travel companions, but you do need to be in the same general ballpark when it comes to travel spending style. Rosa and Rachel both emphasize this point: budget incompatibility is one of the most friction-causing issues in group travel, and it’s one of the easiest to identify and address ahead of time … if you’re willing to have the conversation.

Which brings up another red flag entirely: the friend you genuinely cannot have a direct conversation with. If you’re already nervous about telling someone you want an afternoon to yourself or that you’d prefer a different restaurant, that’s worth pausing over before you commit to a week sharing a hotel room.

How to Actually Prepare When You Know Someone’s High Maintenance

The single best thing you can do when traveling with high maintenance friends is plan ahead and plan together.

Talk about the budget before anyone books anything. Agree on a per-night accommodation range. Discuss whether you’re doing nice dinners, street food, or some mix of both. Figure out if everyone is on the same page about activities. These conversations feel awkward to initiate, but they prevent the kind of slow-burn resentment that can quietly ruin a trip.

For splitting costs, Rachel and her friends have developed a system over multiple trips: one person books things and collects points, the other Venmos immediately, and they take turns covering meals and tickets throughout the trip. When they tally everything up at the end, they’re usually only a couple hundred dollars off and nobody’s keeping a running score of every drink ordered.

Rosa learned the hard way what happens when you skip this step. On a group weekend trip, she found herself splitting a bill evenly after barely touching the shared wine while everyone else worked through four bottles. Her advice? Speak up in the moment if you can, or at minimum, recalibrate your ordering on night two so you’re at least getting what you’re paying for.

The Importance of Having Space (and Friends Who Get It)

Spending too much time with anyone, even your closest friends, in an unfamiliar place can crank up the tension. Stress is higher when you’re traveling. Everything is a little less predictable. And sometimes, you just need a few hours apart.

Rosa has made this work naturally on trips where her family has split up for individual interests: Michael and her friend Michelle peeled off to watch a soccer match in Spain while Rosa and Samantha stayed for a live music event at a museum. Nobody was upset. They reconvened for dinner and everyone was happier for it. That kind of easy flexibility, she says, is one of the best qualities a travel companion can have.

Rachel agrees, and takes it a step further: if you can’t tell a friend you need a few hours to yourself without it becoming a whole thing, that’s a compatibility issue you should address before you’re 10 days into a 14-day trip.

When Things Go Wrong (Because They Will)

Things will go wrong. That is not a pessimistic statement either. It’s just travel. Flights get canceled. Key cards malfunction. Someone gets food poisoning in a cave hotel in Santorini with no ventilation and one bathroom. (Rosa and her two best friends lived this in Greece and somehow remained best friends, so there is hope.)

What separates the great travel companions from the exhausting ones is how they respond to the unexpected. The constant complainers make a rough situation feel impossible. The flexible ones roll with it, find a solution, and usually end up with a story worth telling. Rosa once got her Dominican Republic hotel room upgraded to an ocean-view suite because she calmly made the case that the malfunctioning key card situation was genuinely unacceptable. Sometimes advocating for yourself is exactly right. The trick is knowing the difference between that and just narrating your misery to everyone around you.

Knowing When to Politely Not Travel Together Again

If a trip was rough enough that you’re not eager to repeat it, you’re allowed to say no to the next invitation … diplomatically. Rosa’s advice is to be honest if the friendship can hold it: “I’d love to travel with you again, but maybe somewhere a little more budget-friendly” is a real conversation you can have. If the friendship can’t hold an honest conversation like that, a well-timed “I have work that week” will do just fine.

What’s worth remembering, though, is that some bad trips are just circumstantially bad. Canceled flights, illness, wrong seasons, these aren’t character failures. Before you write off a travel companion entirely, consider whether the misery was situational or whether it was actually about them.

The Best Quality in a Travel Companion

When Rachel and Rosa were asked what makes someone an ideal travel partner, the answer wasn’t some lavish compatibility checklist. It was simpler than that: someone easygoing, willing to share opinions and make decisions, and genuinely open to having a good time. Someone who won’t make you feel guilty for needing an hour alone, won’t silently seethe about dinner costs, and won’t spend the whole trip wishing they were somewhere else.

Traveling with high maintenance friends doesn’t have to ruin the experience, but knowing yourself, setting expectations early, and choosing companions wisely goes a long way. You’re spending real money and real PTO on this. You deserve to actually enjoy it.

Listen on APPLE PODCASTS | SPOTIFY | YOUTUBE

Have your own high maintenance travel companion horror story? Rachel and Rosa want to hear it — drop it in a review or reach out via the Bon Voyage Besties Google form. New episodes every week on Spotify, Apple Podcasts, and YouTube.