Think You Found a Great Travel Buddy? Have This Talk First.

Planning on traveling with someone for the first time? Maybe your intended travel partner is a lifelong friend and you’ve always wanted to see the world together. Or maybe you simply want to avoid paying a single supplement, so you’ve invited a new friend on a trip and you think you two will really click.

Either way, traveling with someone for the first time can be risky business.

On the plus side, the shared adventure might bond you for life and mark the beginning of a deeper friendship. Alternately, you might find (alas, after it’s too late) that you are the least compatible travelers on earth, souring your adventure or, worse, causing a rift in your friendship.

We’re here to help. Before you pair up for the trip of a lifetime—whether a walking adventure or some other journey—talk openly with your potential travel buddy about each other’s personal habits and temperaments. Because the only rocky patches you want to encounter are the ones you’ll find on the walking trail. Here are some conversation starters:

How far are you up for walking each day?

Having similar fitness levels can boost your relationship in many ways. There’s nothing like a good long walk to foster a good long talk. Plus, it’s just plain rewarding to be able to say you fully experienced a walking journey as a “thick as thieves” duo. However, some travel companions move at different paces or have different abilities. And that’s okay. Whether all-day walks or shorter walking excursions appeal to you, share your preferences with your travel buddy so neither of you will feel undue pressure.

Do you like every minute planned? Or do you prefer spontaneity?

There’s a lot to be said for keeping to a schedule. Maybe you’ll squeeze more experiences into your day or have time to chill at the pool or over a cocktail. Then there are the folks who banish all thoughts of calendars while on vacation; they long to linger a while in a village or fall into a meandering chat with locals. The better you understand each other’s styles upfront, the more space you can give each other to “just do you,” even if that might mean going separate ways for an afternoon or even an entire day.

When you’re not on the trail, what would you rather be doing?

Maybe you’re a museum-goer. Or maybe you have your eyes open for a spot where you can rent a bicycle or a kayak. Some travelers can’t get enough of local culture and exploring the wilderness. After all, you might never come this way again. Then again, after walking all day, you might be ready to rest your body and settle in with a good book or your journal. Know what to expect from each other so there are no surprises.

Are you a late sleeper or an early riser?

On a Country Walkers Adventure, we like to get a reasonably early start. Still, it’s your vacation. And it’s okay to skip a morning’s scheduled stroll if you’d rather sleep in and enjoy a leisurely breakfast. It’s also okay to be up before sunrise and partake of a vigorous walk at dawn. It’s perfectly acceptable if you and your companion aren’t on the same sleep cycle. And that’s fine: You might be traveling together, but it’s no fun to be chained to each other. Each of you needs to experience your destination on your own terms.

Introvert or extrovert?

Introverts often prefer the company of their own thoughts, while extroverts thrive on the energy of socializing. As you might expect, they are very different travelers. It can be exhausting for introverts to feel like they have to be “on” when surrounded by other people. Likewise, it can be exasperating for extroverts to feel like they’re having a one-way conversation with introverts. Which are you? Which is your traveling companion? Be sure you understand and respect each other’s styles.

What’s your idea of relaxing in your room?

Remember that you’re sharing more than a travel experience. You’re also sharing each other’s idiosyncrasies and habits. Your travel buddy is also your roommate, after all. And if your idea of feeding your soul after a long walk is dancing in your room to loud music while your roomie’s idea involves sitting in bed with an absorbing book or a pen and journal, you’ll need to decide ahead of time who gets the room on which days.

As you might have gathered, it’s communication and compromise that make a trip with a new travel buddy run smoothly. But maybe there are things you’re not willing to compromise. For instance, what’s a visit to Italy without learning about its cuisine during a cooking lesson? Why go to coastal France if not to walk out to Mont-Saint-Michel?

Yes, compromise is a critical component to a successful journey. But be sure you’re clear about the non-negotiables. Respect your companion’s bottom lines as much as you want them to respect yours.