The Playbook For The Modern Man

How To Travel With Friends & Not End Up Killing Each Other

The art of vacationing with an entourage (and still liking each other when you get back).

Arthur is a nervous flyer. Barney gets car sick. Calvin is a picky eater. Danny’s a control freak. Ed is a cheapskate. Fabio can’t keep his face out of his phone for longer than 5 minutes, and Gus has been MIA since you arrived. You’re barely a day into your trip and already you need a vacation from your vacation. Maybe Contiki would have been a better idea after all…

As Mark Twain said, “There ain’t no surer way to find out whether you like people or hate them than to travel with them.” A holiday with your mates could be an epic experience full of once-in-a-lifetime memories — or an expensive death match of awkwardness, animosity, and subtweeted bitching.

Yet despite the obvious risks, get enough beers in and it’s almost inevitable that someone will suggest getting the band back together for the brocation to end all brocations. Before embarking on an adventure with your entourage, here’s what you need to know to keep your sanity and friendships intact.

Choose Companions Wisely

Keep the wrong company and your group holiday is over before it begins. Every candidate must be evaluated based not only on how well they get along with you, but also on how well they’ll mesh with the rest of the crew. Aim to assemble a squad with similar – or at least complementary – interests, energy levels, travel experience, budgets, habits, communication styles, and social skills. If you love late mornings and lounging by the pool, you may not want to travel with your survivalist backpacker buddy. Also beware of: High-Maintenance Henry, Penny-Pinching Pete, Sloppy Drunk Dennis, and Socially Awkward Ivan.

Set Clear Expectations

Once you’ve assembled the Avengers, make sure everyone is on the same page about the basics. Just because you all want to go to Thailand doesn’t mean you want the same thing out of it. There’s conflict ahead if one person is thinking beaches, another is into temples, and a third is all about the Full Moon Party. Likewise, battles are brewing if one person expects 5-star stays and another only has a hostel budget. Have everyone consider their goals, expectations, and travel styles before booking anything, and construct a rough itinerary everyone can agree on prior to take-off.

Plan A Path

Unless you’re travelling as part of a packaged tour, expect to waste time discussing what to do. You will lose precious minutes debating the merits of subways vs taxis and tourist highlights vs local hotspots. Minimise those moments by compiling a plan that eliminates the need for any major decision-making on the fly. Give everyone an opportunity to contribute. Then arrange an itinerary by including as many requests as possible, merging similar or conveniently-located activities, and trying some things that are completely new to everyone.

Make Organising Easy

You’re on the same page in theory, now make it literal. Organise the details of your adventure in a way that is accessible and understandable to all parties involved. Use Google Docs and spreadsheets to share itineraries, budgets, phone numbers, packing lists, etc. Create a shared calendar to schedule activities. Use a private Facebook group or event to centralise all communications. Download an app like TripIt to put all your travel plans in one place.

Money Talks (Have Them)

Money makes the world go around, but when you’re going around the world, it can be a serious source of contention. Talk travel expenses upfront as it could be a deal-breaker for some people, and the most sensitive subjects are best tackled before take-off. Creating a trip fund to bankroll shared expenses works well for some groups, while others prefer to pay for all expenses individually. And that’s only two of many, many permutations of a viable group travel financial plan. Your mileage may vary, but these things are certain: it’s not worth it to fixate on a few dollars here and there, and the only answer that’s actually wrong is “Eh, we’ll figure it out later.”

Pro tip: if your crew is big enough, look for group discounts on activities and attractions. A travel planning service may be best equipped to help you and your roving horde take advantage of your group status.

Divide And Conquer

Play to your strengths. Assign each group member a role based on their interests and skills. Make the most fair and decisive person the group leader. Make the Bourdain wannabe the trip cook. Put the obsessive organiser in charge of research and scheduling. Other members could be the resident photographer, driver, bookkeeper, language expert, weather tracker, accommodations finder, or GPS navigator. No one likes a control freak, and relying on one person to do all the planning and booking is a surefire way to build resentment in your relationships.

Be A Conscientious Packer

The key word here is “light.” Don’t be the asshole hauling around half his possessions, holding the group up at baggage claim and pitching a fit every time you encounter an unexpected staircase. Pack what’s necessary so as not to be a drain on everyone else’s resources and leave the rest at home. Decide ahead of time whether you’ll all be checking bags or strictly using carry-ons, and for certain gear that can be shared, create a collaborative packing list to avoid carting around duplicates you don’t need.

Arrange Accommodating Accommodations

Be extremely thoughtful in your choice of lodgings. Are there enough bedrooms? What size are the beds? Who gets the master? Will the snorer have a roommate? Is there sufficient storage space? How many bathrooms are required to accommodate everyone’s morning shower? Shared living space can feel like a return to your college dorm glory days or a prison sentence with no parole. Chat ahead of time about what’s most important to the group: saving cash by bunking up, or splashing out to have more space.

Go With The Flow

Practice patience, communication, and compromise. Know that you will not see or do everything on your list (for that matter, neither will your friends). Some days you may pay more than your fair share for dinner. Some days you may be late because someone needed a bathroom break. Some days you may have to take the middle seat or the bottom bunk. Make peace with it. Remember that in exchange for a little give-and-take, you get to share an incredible experience with your favourite people on the planet.


Sometimes the flow just isn’t flowing. When that happens, speak up before the issue has a chance to fester and intensify. There is such thing as being too laid-back if it means burgeoning resentment. You cannot ignore anything into submission. Deal with problems as they arise, before too much tension builds and someone throws a punch.

Take A Break

Too much togetherness is a recipe for catastrophe. The easiest way to travel harmoniously is to part company for a bit, giving individuals time to recharge and explore interests the group doesn’t share. Make free hours part of your plan, perhaps even scheduling an entire day or two to be spent separately. Someone may come back with your next great group adventure.


Be overly ambitious. Forget to plan downtime. Make any decisions while tired, hungry, or stressed. Spend too much time glued to a screen. Get judgemental when the pressures of travel bring out the weirdest and worst in your pals. Maim anyone out of frustration.

RELATED: The Top Destinations For Men Travelling Solo



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