Avoiding Travel Drama: Best Practices for Traveling Together
Some photos make it clear why I wear so many hats. Here’s me on a tour bus with traveling companions in Brussels, Belgium. August 11, 2022.
I’ve had overall good experiences traveling with people other than my spouse or partner and immediate family—though all of us who’ve traveled with other people have had our share of disasters. And as with so many aspects of life, the disasters always stick in mind.
Always a fan of thinking through how to do it better next time, I’ve outlined best practices that I’ve learned to make traveling with other people easier than it might be otherwise (and avoid as much as drama as possible).
Of course, we all have friends and family we love and enjoy beyond measure—and with whom we cannot travel, no matter the precautions taken before and during the trip. Even these tips won’t help if you decide to travel with someone with whom you mesh better in smaller doses and with fewer logistical requirements!
Golden Rule: Set Expectations
As with most things in life, happiness comes through setting expectations.
True if you’re setting expectations for yourself and something you’ve planned to do solo—and true when coordinating activities with other people.
For travel with other people to come off successfully, which I define as everyone enjoying the trip during the trip and leaving with positive memories for the long term, you need to set expectations at the beginning of your trip-planning period and you need to hold to these commitments during your travel experience.
Expectations for what, you fairly ask. And how do you set them?
Let’s look at the most common snags when traveling with other people and address how you can plan in advance to avoid them.
What’s Your Budget?
Some people have extensive budgets for travel in general or have budgeted for a particular trip for a long time because it’s a dream location.
Some people always travel on shoestrings and some need to do so some of the time, depending on life stages and events.
Does this mean these people cannot travel together?
Not at all!
Having different travel budgets simply means you need to clarify well before you leave—at the start of your planning process—general budgets for each person or each component group (e.g., couple). Do so without judgement or embarrassment.
Remember: In life, we all have different budgets for different things and in different moments. You might never spend more than a few dozen bucks on a watch while your friend spends large capital sums—while you plan to high-roll on a vacation and the same friend prefers low-budget travel options. You should not allow your buddy’s massive or meagre budget for this trip—or vice versa—to have any bearing on your buddy, you, your friendship, or your travel experience together.
You then need to understand that these budgets, if they vary between people and groups, may mean that you overlap for certain activities and not on others.
Whatever these separate things are—be okay with it! Your goal is to spend some time together, to experience some things together, and to enjoy the company of others in a different place. You don’t need to glue yourself to your travel companions at all times to have fun and enjoy the trip.
Who’s Responsible for What?
Decide who’s handling what aspect of the planning and the programming before and during your travel.
For example, once you’ve addressed some of the other questions in this article around budgets, preferences, and activities, someone may decide to run point on finding options for accommodation and someone else may take charge of getting tickets to certain sights and activities. Someone else could do the research in advance—and on the ground, in the moment—to find spots for eating and drinking during the trip. Another person or two could volunteer to be the navigator during the voyage, guiding everyone from point to point, which can involve planning in advance plus planning while in place, from reviewing maps to purchasing the data plan necessary to use their smartphone’s GPS (and likely both).
Make these responsibilities clear to everyone. Write them down, if needed.
What you don’t want to have happen is everyone showing up and thinking someone did something—when that person assumed someone else had it covered.
How Do You Like to Travel?
Different people, different travel styles.
Some people plan each day down to the hour. Some people prefer to book travel to the destination and then figure everything else out in the moment, all the way down to where they’ll sleep on the first night. (Yes, I have traveled with someone like that.) Some people love seeing all the major sites and doing all the tourist activities—and some don’t want to do any of that.
If you have significantly different travel styles, you may not be ideal travel companions (and that’s okay). Someone who wants to have nothing planned other than how they will get to the destination will only stress out someone who wants to have each day’s program locked in place from wake-up time through bedtime.
However, given that most people fall in the middle of the travel-style spectrum, you likely can travel with most people if you align early on how your travel styles differ and what that will mean for your trip. Traveling with someone with a different travel style than your own means that you will overlap more minimally than you would with someone else who has a more similar travel style. For example, perhaps you link up for certain meals and activities that you both consider must-sees and must-dos.
Just remember: No frustration when your planner friend plans and you want to just do whatever—or the other way around. You were each warned, so roll with it and let them be them and you be you. You don’t have to do everything the other person does.
When it Comes to Food and Drink, Any Preferences?
Someone prefer to eat street food or picnic when on travel? Someone prefer only sit-down restaurants for all meals? Someone prefer to cook in at the rental property?
Personally, I eat one sit-down restaurant meal per day while traveling. I like one space during the day to sit down, enjoy a cooked and prepared meal presented to me as I relax and enjoy. The rest of the time, I picnic, eat in the rental apartment, or pick up something to munch on the move.
However, I know other people who prefer to eat three full, sit-down meals—and sometimes snacks and coffees—in sit-down restaurants and cafés.
Some people—like me—aren’t big drinkers. (Well, I drink a lot of water and tea, granted. Read “drink” as “alcoholic beverage” here.) Others like to end every evening at a bar while on travel.
If you and your travel companions have differing preferences when it comes to how you like to eat and drink while on travel, find a happy medium or plan to meet up for only one meal per day, whether in a restaurant, café, or the rental property.
Maybe that means everyone does their own food thing except for dinner. Maybe it means you eat out more than you would traveling without these companions. Maybe you end up in a bar a couple nights on your trip—and you’d never go into one otherwise, even at home.
You do not need to eat and drink together at all times on a trip, but you should try to gather for a meal and a glass of something at least somewhat regularly while on travel with other people for the pure conviviality of it. In these settings, you get to relax together, catch up on life in general, and talk about your trip.
What Do You Need or Want in Accommodation?
Camping? Hostel? Hotel? Rental property? What parameters and requirements for each?
When you start asking this question, you’ll find a range of answers—and they might surprise you. A person you thought wouldn’t stay in less than a four-star hotel prefers paying as minimally as possible for accommodation on travel, for example. All good—just smart to establish these preferences before you start planning.
Key point to understand: It’s okay for one person or group to stay in one type of vacation property and another person or group to choose something different.
Accommodation is not an area where I’d recommend people compromise on their preferences, as where people rest, sleep, and store their belongings on vacation ties closely to that person’s overall enjoyment of a vacation.
On trips in Switzerland and Belgium, one couple (us!) stayed in a rental apartment and another couple, preferring help with luggage and other hotel-only services, stayed in a hotel. These arrangements made more sense for us than asking one couple to have fewer amenities than desired and asking the other to pay more than they wanted for a place of stay on that trip.
You may even both want rental properties—but find that you’d prefer different types or find that to get what you want, you must get two or more places to have the right parameters for everyone.
At the very least, to avoid time lost getting together and getting back to base for resting and resetting, aim to find accommodation in the same neighborhood. I target having no more than a fifteen-minute walk between different people’s accommodation.
Have any Must-Sees and Must-Dos?
If you love art museums and your travel companions do not, neither of you is wrong. If one of you has been to the destination before and another has not, you’ll likely want to see different things while there. Some people want to pass their time in the area’s surrounding nature on hikes or in the sea—and some people will go to the resort’s spa instead.
I’m not a skier, for example, but I love a cabin in the snowy mountains where I can cozy up and read, peppering my hibernation with short snowshoe treks. For these trips, my skiing companions can head to the slopes all day without me feeling bothered in the slightest.
Likewise, I’ve traveled with people who had zero interest in visiting the museums and landmarks that I had top of my must-see list.
Did I ruin the trip for my skiing friends? Did my friends who didn’t care for art ruin my big-city visit? Not at all—though I would have ruined the day for certain if someone had forced me to ski, and I don’t think I’d have enjoyed the museum as much if my travel companion stood alongside, grinning and bearing it on my account.
Of course, if you feel it critical that some aspect of the trip is done in a group or with someone else, you should state this in advance. Maybe you’ve always wanted to try bungee jumping, and this famous cliff in your destination is famous for it—but you don’t want to do it alone and your traveling companions find the mere notion fear-inducing. Maybe you don’t want to ski alone every day, each day of your trip, while your friend stays back in the lodge or town.
Fair enough. Really.
You just need to set out these understandings in advance. Otherwise, people will feel pressured to do things they do not want to do, to save your experience (at risk of ruining their own), or people will feel disappointed or surprised by needing to undertake activities solo that they’d imagined doing with the group.
Before you leave for your destination, determine what everyone wants to see and do. While there, do the things that overlap together and then do things that don’t overlap separately or in smaller groups and meet up with the larger traveling set later for food, drink, or the next activity.
Ensuring a Good Traveling-Together Experience
If you’ve established expectations and come to understandings in advance, you’ve reduced the likelihood that someone in your travel group’s frustrated or hurt when someone else doesn’t go to the bar every night, or someone else chooses not to eat out every day, or someone else skips an attraction in favor of another activity. You’ve also limited the possibility that everyone shows up in the destination without a key piece of the voyage covered, whether that means tickets to must-sees—or rooms in a hotel.
One of the joys of traveling with other people is having other people with whom to share the experience. Yet another, less recognized joy, is that when you’re traveling and have moments apart, doing things separately, you get to gather back at the next meet-up moment to share fun stories about what you’ve done on your own.
And if you’d like more trip-planning guidance, read my post about how I plan my trips for ideas!