How to Travel with Other People and Not Have a Bad Time

How to Travel with Other People and Not Have a Bad Time
Some links in this post are affiliate links—that means that at no extra cost to you, I may earn a small commission if you book through them, which helps keep the blog running. As an Amazon Associate, I earn from qualifying purchases.

When it comes to time to travel with other people, human beings fall into two categories: those who love it and those who would rather not.

If you’re like me and fall into the ‘hard pass’ category, deciding whether or not to travel with other people isn’t so simple.

And if you’re on team, ‘the more, the merrier,’ you may have struggled to find good adventure companions and instead found yourself in some shit situations.

Luckily for you, I’ve made every group travel mistake in the book!

Here’s my guide on how to travel with other people (and not have a bad time).

Universal Tips for any Situation

traveling with friends in Puerto Rico

Often, the most important things get overlooked because they are so essential. These tips apply to pretty much any travel situation involving other people.

Group travel hacks

  • Keep the line of communication open. This could mean having a group chat, meetings leading up to the trip, a shared Google Doc itinerary, or anything that keeps you in contact with your travel companions.
  • Don’t be afraid to talk budget. Some people like to travel as cheaply as possible, while others view spending money as part of the experience. Whatever the preferences may be, they need to be clearly defined by both people.
  • When it comes to hotels and rentals that are split, always pay your way and never ‘deal with it later.’ Money, like alcohol, can make people act out of character. If you’re splitting the bill, pay them right away instead of at the end of the trip. If you must wait, apps like Splittr or Splitwise will help you keep track of shared expenses.
  • Take time for yourself. Whether you’ve been BFFS since 8th grade or you’re all super extroverted- everyone needs some ‘me time.’ This becomes more important the longer the trip is. Something as simple as popping in your headphones for 30 minutes to listen to a podcast or music you love can help you recharge your social battery.
  • Always be flexible. While planning is important, adapting to changes and going with the flow is an essential part of any vacation experience.

Tips for Traveling with Close Friends

Two best female friends smiling and traveling together at Garden of the Gods, Colorado.

In theory, a friendcation is a no-brainer.

While you might enjoy someone’s company over brunch, at the gym, a getaway with the same person could be a shit show.

What to ask yourself before traveling with a friend

  • Do you know this person? I mean, truly know them beyond the occasional catch-up text or brunch. Are they someone who your other friends like and trust? How have they changed since you first met them?
  • To what extent do you trust this person? Remember that you’ll likely be sleeping in the same room as them, where they will have access to your belongings.
  • Has this person traveled much previously? More experienced adventurers may need to guide newbies and do the bulk of the planning. The inexperienced person may also have more anxiety or different expectations of the trip.
  • Do you have similar interests to this person? If you love hiking and being outdoors and they don’t, the itinerary may need to be compromised.
  • How close are your body clocks? This may seem like a weird consideration, but picture this: You’re ready to explore outside, but your friend is ready to shop the boutiques and sip cocktails. You wake up early, ready to go, but the other person is a night owl.
  • Do you both expect a similar level of activity? Take it from someone who has learned, over and over, the hard way, that ‘I like to hike’ has a very different meaning depending on who you ask.
  • Is one of you a planner and the other spontaneous? Personally, I feel this can be a lucky travel combination that encourages flexibility if communication is clear.

Traveling with Strangers

Disclaimer: Always use your best judgment and never travel with anyone that makes you feel even the slightest bit uneasy.

Why travel with strangers?

Just because someone is a good friend doesn’t mean they are the best person to travel with…most of us have pals who don’t share our burning passion for seeing the world.

Personally, as a woman, I would never consider traveling anywhere with a man I didn’t know, nor would I advise any other woman to do so.

And on a more positive note, some seriously incredible friendships have been formed by women worldwide united for the same reason- wanderlust.

Tips for vetting travel companions

  • How authentic is their profile? This goes without saying… but if someone’s profile photo is an anime character, they have virtually no friends/followers and rarely show their actual face, that person is likely hiding something. Don’t find out what that is. Just leave it alone.
  • Search their profiles for ‘Facebook drama.‘ You know the type- every post is negative. Someone has wronged them. They are constantly in recovery or otherwise seeking help or validation for some terrible situation where they did nothing wrong. Always stay away from these people.
  • What other online sources give this person validation? Are they friends of friends? Are they in travel groups with you? If so, search their name and see what kind of things they’ve posted and commented on.

Group Travel Hacks

Road trips best friends outside Pike's Peak National Forest demonstrating how to travel with other people in a group.

For girl’s trips, commercial tours, family getaways, or just friend extra large friendcations, traveling in groups is guaranteed to create lasting memories- for better or for worse.

The more people are added to any given situation, the more complex that situation will become.

Personalities mix, travel brings out both good and bad stress in everyone, and new anxieties can manifest with new experiences.

Being able to travel with other people is a learned skill.

What to prioritize when planning your group trip

  • Cutting costs. Consider whether shared items such as tours or hotels are best booked separately. The price of flights can drastically increase if purchased together instead of individually.
  • Book early. Make sure you secure your lodging early to get the best deals and have enough space for everyone. Larger or grouped rooms may sell out more quickly. Feeling cramped is a fast way to make everyone feel frustrated.
  • Consider alternative accommodation. Often, you can get luxury or unique places for an affordable price when the cost is split several ways. Staying in an apartment or house instead of spread-out hotel rooms gives the group a chance to cook meals and hang out communally.
  • Look at the big picture. Bring a lightweight tripod to capture group photos and prevent anyone from feeling left out as the photographer.
  • Group rates. Check if there is a group rate that you can take advantage of, especially for tours and transportation.
  • Take control of your sleep. If you’ll be sharing a room, pack some quality earplugs and an eye mask to help you sleep.

Traveling with Family

Courtney Lux and her mother traveling with other people through Italy.

Traveling with family can easily be the most stressful and transformative of all the situations on this list.

Nobody triggers you quite like family. Nobody can catalyze a healing experience from an everyday situation quite like family.

The road trip I took with my mother to New Mexico was one of the best times of my life. We laughed, cried, shared experiences, and worked through problems together.

I highly recommend everyone take a trip with a family member at least once.

The sooner, the better, tomorrow is promised to no one.

Tips for a successful family trip

  • Be patient, especially when there is an age gap. Older people can be set in their ways and less able to adapt to changed plans or disappointments. The older generations also tend to internalize their feelings more as a byproduct of their time, and their anxiety can manifest as complaining or frustration.
  • Prepare to meet them where they are. If you know they want to see the Grand Canyon, but you’re a hiker, and they’re more of a ‘snap photos at viewpoints,’ be ready to accommodate that. Family trips are more about the people you’re with than what’s happening in the physical world.
  • Remain present. Traveling with family is a luxury, a privilege, and not something that most people in the world will get to do. Remember to put the phone away, spend a little less time doing activities alone, and be grateful for the moment you’re in.

Just remember that life is hard, travel is scary, and we’re all doing the best we can with what we have.


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group travel for girls trips or staycations

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Some links in this post are affiliate links—that means that at no extra cost to you, I may earn a small commission if you book through them, which helps keep the blog running. As an Amazon Associate, I earn from qualifying purchases.

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