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Kendal at Oberlin Blog

Pros & Cons of Vacationing with Your Friends

Posted by Molly Kavanaugh on Mar 17, 2017 10:33:05 AM

kao-vacationing-with-friends.jpgYou can pick your friends, but not your family. And many of us are blessed to have an array of friends who have diverse interests, abilities, lifestyles and cultures.

But do you want to travel with your friends? Yes? No? Or more likely, depends on the friend.

First there are the basics to consider – time, money and destination. Then comes the tricky part – your personality and your friend’s. Sure, you enjoy each other’s company (or why else would you be friends?), but spending a week or longer away from home is a lot different than hanging out in familiar surroundings.


Test the waters of traveling together with these destinations that are only a few hours away.


You might enjoy shopping for holiday gifts together, but when you travel, you prefer museums over gift shops. You’re a night person and prefer a leisurely breakfast to start your day, while your friend wants to be first in line. Your friend likes to sample local cuisine, while you feel more comfortable at restaurants with a familiar name. The list goes on and on.

Pluses of Traveling with a Friend

From picking out a destination to looking at photographs once home, you are not alone. You can share the experience from start to finish, and long afterward, with someone who is special to you. Sure, if you go on a group tour, you might make new friends, but maybe not ones that develop into an ongoing friendship.

The trip is cheaper if you travel with a companion. You can split gas and vehicle rental costs. You can share a hotel room, a cab ride, groceries, a guidebook and more, and save money. And speaking of meals, if you travel solo, you’ll probably be eating alone most of the time.

There can be safety in numbers, especially if you are a woman and like to enjoy the area’s nightlife or have physical limitations. “Your loved ones would be at ease knowing that you are on a journey with people they know and trust,” according to Travefy.

Travel can deepen your friendship. Depending on your destination, the two of you might experience new cultures, help build a home in a foreign land, try a novel activity like snorkeling or horseback riding, hike the Grand Canyon or embark on other adventures.

And there are all the other unplanned activities, from watching a spectacular sunset to falling off a bike and needing medical attention. All these experiences may reveal a side of your friend you never saw before and draw you closer.

Potential Drawbacks of Vacationing with a Friend

Then again, the experience might reveal a side of your friend – or yourself – best kept under wraps. We all have heard stories of people who traveled with a friend and no longer talk to each other. Or are still friends, but the relationship is strained and not as comfortable as it used to be.

Solo travel has its benefits too, guidebook author Rick Steves writes: “When you're on your own, you're independent and in control. You can travel at your own pace, do the things that interest you, eat where and when you like, and splurge where you want to splurge. You don't have to wait for your partner to pack up, and you never need to negotiate where to eat or when to call it a day. You go where you want, when you want, and you can get the heck out of that stuffy museum when all the Monets start to blur together.”

Traveling alone may not be for you, but how do you choose a friend to travel with? It takes planning, just like the trip.

How to Pick the Right Pal

Choose a person with similar budgets and interests. “Vacationers most often disagree about how much to spend and what to do," according to a recent survey from hotel chain SpringHill Suites. If you haven't traveled with someone before, ask him or her about travel habits. At least you'll know what you're getting yourself into,” writes Jason La in the Los Angeles Times.

Because travel is so varied, make sure you both have the same goals. You’re heading to a Caribbean resort, and you plan to sit in a lounge chair by the ocean catching up on all the books you haven’t had time to read while your friend is looking at the list of excursions with excitement. You certainly don’t have to do everything together, but you don’t want to spend the whole vacation going in separate directions.

If you are sharing a hotel room, make sure there is enough room for both of you to be comfortable for more than just sleeping. Maybe you can get a room with a balcony or deck, or select a hotel with common areas, such as a courtyard or cozy lounge.

Talk about personal issues. If you snore, make sure your friend comes equipped with earplugs – or pack a pair. If you like to listen to music while falling asleep, bring a headset for your device. You can’t plan for everything, but discuss each other’s needs and preferences and come prepared.

Have you traveled with a friend? Tell us about your experience and pass along any tips.

Start planning your next adventure


Molly Kavanaugh frequently wrote about Kendal at Oberlin for the Cleveland Plain Dealer, where she was a reporter for 16 years.

Topics: Active Lifestyle

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