Travel Secrets: Friendship & Travel

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Travel Secrets: Friendship & Travel

The only feeling more gratifying than sharing adventure with a friend is reliving the experience, over and over again, during the tale’s retelling. That time you were helplessly lost during a road trip or when you rallied each other to push for the mountain peak. Often those memories grow richer with time, as does the friendship.

Exploring a new place or activity with friends allows us to understand each other and appreciate unique attributes through another filter. Away from the concerns of daily life, we learn what fundamentally makes each other tick, and sometimes, painfully, what ticks each other off.

Yet, regardless of potential pitfalls, it seems more travelers than ever are getting out into the world, closest buds in tow. Chris Vassil, executive producer at Travelzoo says not only are more friends traveling together, they are stretching farther afield. “Nearby weekend trips, like music festivals, have and will continue to be a trend but groups of friends taking more far-flung trips together is becoming more popular,” he says.

David Solomito, Vice President, NA Marketing at Kayak says one of the factors stoking this trend is cost. “Lower cost airlines are making farther flung locations, like Asia, Australia and Europe, more affordable than ever,” he says, adding, “flights to Europe are down 20-30% over the last year making it the perfect time to take that European vacation.”

Bottom line: No matter how far or near you venture, nothing bonds friends like shared experience. Use the pro tips to create lifetime memories with your besties.

Choose Companions with Care
Closest friends don’t necessarily make the coziest travel companions, and that’s okay. For instance, my philosophy that nothing interesting happens before 10 a.m. doesn’t always jive with early-riser friends, so we filter travel opportunities accordingly.

Define individual ideals to determine if travels styles mesh. “Not everyone enjoys the same type of vacation, so it’s important to discuss trip preferences beforehand,” says Solomito. “Consider whether you’re a lounge all day by the pool type of traveler or more of an adventure seeker.”

Seek a sweet spot with complimentary versus identical styles. For Jen O’Neal, founder and CEO of, different interests, within reason, add to discovery potential. “Traveling with friends and family with different hobbies, food preferences, or even activity levels is a great way to see and do more on on a trip than you would traveling solo (or with people with similar interests),” says O’Neal.

Start Small and Near
Test drive before launching into resource-intensive adventures. “Consider a day trip or even a long weekend away before committing to anything longer,” says Solomito. “If the day leaves you wanting more, you will likely be compatible travel partners.”

Vassil recommends going domestic initially. “Traveling internationally can really put a strain on friendships—the trips are more expensive (so there’s more at stake), you’re spending a great deal of time together, jetlag makes ALL of us cranky, and you’re in a completely different environment and out of your element, so the margin for frustration between friends is high!” he says.

Consider Activity
Pinpoint an anchor activity or event. “Traveling with a specific goal or event will make the trip more enjoyable for everyone,” says Solomito. “Not only does it give you something to look forward to, but it also provides you with a notable event to plan around. Consider concerts, a special show, or even a sporting event for your next trip with a friend.”

Discuss bucket list items to ensure your interests align (or happily agree to individual pursuits) and be upfront about desired activity levels. “While some love a jam-packed agenda when they travel, others may prefer to lounge around all day,” cautions Solomito. “It’s important to get on the same page before the trip begins to avoid any conflict during it.”

Set Expectations
“What’s the ultimate goal of the trip?” asks travel blogger Paula Dixon of Curly Hair Adventures. Dixon and other experts recommend asking a range of questions:

Do you prefer guides or independent exploration? Are you interested in the area’s history? Is museum hopping on your agenda? Are you motivated by budget or luxury?

“Being able to identify everyone’s goal makes it easier to plan your itinerary and helps ensure that everyone is getting something they want,” says Dixon. “Otherwise, some people will be upset and annoyed throughout the entire trip, which will in turn make everyone irritated.”

Accommodations and transportation are often trigger points. If you prefer the buzz of a hostel while your friend dreams of a quiet Airbnb or lux resort, your vacation dreams may not overlap. Same goes if your friend craves the freedom of exploring by rental car and you long for the simplicity of public transportation.

Remember, individual preferences aren’t wrong, just different. Be honest and open to compromise, yet don’t lose sight of your own dreams.

Divide & Conquer
Embrace your unique talents and strengths. “Decide who of the group is responsible for putting together a program and making the bookings,” recommends travel blogger Sofie Couwenbergh of

Elect a chief navigator, activities director, lodging guru, and culinary specialist and encourage each other to hone skills. Dixons says to keep in mind some friends are great at reading maps and solving problems in real time while others excel at creating photo opps or keeping everyone on schedule. Have fun with assignments and trade roles when necessary.

Talk Money
Discussing budget with travel companions can be tricky, but necessary. Solomito says setting perimeters in advance means you don’t end up debating whether dinner is at an acclaimed Michelin restaurant or corner hot dog stand.

Also, decide upfront how you will handle joint expenses, such as lodging or bar tabs. “At some point, there’s a good chance that splitting the cost of things will get messy,” says Vassil. “Either be flexible—i.e. we’ll pick up the tab this time, you grab the next one—or come up with a good game plan that works for everyone before you start the trip.”

Enlist the bill splitting prowess of an app like Divvy to easily transfer funds.

Embrace Space
Travel together does not mean spending every moment together. Seek out solo activities to grow and explore individually. “Realize that needing alone time is just fine,” says Couwenbergh. “It’s not because you’re traveling together that you constantly need to talk to each other. Bring a book or your iPod for travel time and down time and don’t feel guilty about it.”

O’Neal agrees individual pursuits can make travel more interesting for everyone. “Plan to meet up at the end of the day for dinner where you can catch up about all your new discoveries!” she recommends. Stretch your travel legs further by exploring nearby destinations separately, then rendezvous in a new spot.

Nurture the Bond
Choose friend over phone. “While you might want to post about your trip on social media and have long drawn out conversations with people online about what you’re experiencing, you have to remember that you’re experiencing the world with some of your best friends – and they deserve your undivided attention,” Dixon says.

O’Neal suggests when problems arise to seek resolution immediately. “Getting to the root of the problem—do they need some alone time, do they want to do other activities—rather than letting it fester will make your trip much more enjoyable,” she says.

Remember, we all get on each other’s nerves from time to time, and that’s okay. Don’t be derailed by little annoyances. Live in the beautiful moment and be the kind of friend you want to travel with.

And, perhaps most importantly, never, ever travel without earplugs. Everyone snores, and that’s okay too.

Main photo by Alessio Jacona/ Flickr CC BY-SA 2.0
Lead photo by Paolo Gamba/ Flickr CC BY 2.0

As a kid playing in Alabama’s red dirt, Jess Simpson fantasied about exploring faraway sands. She still chases those dreams every day and aims to nudge fellow dreamers to explore farther, deeper, and more boldly. Read about her digital nomad adventures at Intrepid Travel, Mental Floss, Fodor’s, Bustle, and her bi-weekly Travel Secrets column here at Paste Travel. Connect via TwitterFacebook and Instagram.