Travel Companion Disasters

The right travel partner will determine the success of your vacation. Will you board your plane home, already missing your travels? Or will you be happy to go your separate ways, more relieved than disappointed that the trip is over?

Vacations are expensive, and they’re often few and far between. Traveling with the wrong person/people can be a disaster, and it can make your time away feel more like a disappointment than a new experience.

Here’s my foolproof list of questions to ask yourself and your travel partner(s) before embarking on any trip. Compare your answers to check your compatibility:

Are you a laidback lounger, a champion sightseer, or half and half? Incompatibility in this area can create huge issues for travel companions. I’ve been on vacations with people who want to sightsee from dawn til dusk, and I’ve been on vacations with people who want to sit on a beach with a drink in their hand all day.

While both can be appealing depending on the setting, chances are, you fit in one group more than the other. If you’re a half and half, like my husband and I, it’s important to choose flexible travel companions who are comfortable with periods of leisure time to balance fast-paced sightseeing.

Choose travel companions who are similarly paced so that you’re neither wiped out nor completely bored. For us, we don’t want to exhaust ourselves on vacations. We don’t have enough time to take a vacation from our vacation!

Are you traveling on a strict budget? Money creates stress. It can cause tension in your trip if your companion is far too spendy on dinner and activities when you’re trying to maintain a budget. Be sure that you either have similar budgets or are comfortable saying, “No, that’s not in my budget for this trip.”

If you aren’t comfortable asking your travel companion(s) about their budget, mention your own. Money conversations are awkward, but they’re far more awkward when you’re standing in France debating between the simple, affordable café on the corner or the five-star restaurant you read about in Condé Nast Traveler.

Museums, tours, wine, and top restaurants add up over the course of a week, especially when paired with airfare, hotels, and transportation. Be prepared and avoid (unnecessarily) stressful spending.

Do you prefer organized tours or unorganized exploration? For the most part, I’d rather forego most museum visits to spend an afternoon wandering with a map. For others, it’s all about guided tours and museums. Both are great ways to envelop yourself in a new culture, but they’re very different….and they often indicate different types of travelers.

Nothing will be more frustrating for an art lover in Paris than to realize that their travel companion doesn’t want to visit the Musée d’Orsay. Make a list of must-see locations for both of you as you plan your trip. Ideally, there’s enough time to accommodate everyone’s top choices. If you don’t have a single item in common, you may want to reconsider your travel partner(s) to minimize stress and maximize your experience.

Do you want time/space to yourself, or should the group stay together? This is a seriously awkward topic for most. As my husband and I get older, a handful of our “couple friends” have suggested going away together. In most cases, we would love to travel with a small group of couples, but it would be absolutely essential that we have the option of taking time apart. Not only for situations in which the couples want to see different sites, but also to have the ability to relax, recharge, and have some “alone” time on vacation.

This also applies to groups of singles. If you are concerned about too much “together time,” tell your friends that you may take an afternoon or two on your own. Avoid offending anyone in the moment by being clear from the outset.

Do you like traveling on foot and challenging yourself physically? Many people may forget about this one…until they’re on vacation with Susie Fitness and Adventure Andy, complete with a suitcase full of exercise gear and Power Bars.

Okay, that’s an extreme example, but people tackle sightseeing in many different ways. Some are so energized by their new surroundings that they want to take a 3-mile morning jog in the city, followed by a day of sightseeing on foot. Others might want to use cabs and tour buses to get around, while more frugal travelers may prefer public transit.

Tensions can run high if you’re springing for a cab to each destination when your friend wants to rent bikes, or if you want to walk and your companion wants to take the (scary, foreign) subway. Add this question to your travel questionnaire as a final compatibility check.


I remember, after our very first trip together early in our relationship, my in-laws said something along the lines of, “Well, we knew you’d either end this trip more in love than ever or you’d end it by going your separate ways” (which, now that I think of it, doesn’t make our relationship sound very solid if one vacation could make or break it, but you get the point). Vacations can ruin friendships and end relationships…or it can leave you feeling more connected and more in-tune with each other. You’ll know right away which category you and your travel partner(s) will fall into, but, to be safe, reference the above checklist and take a day trip to test the waters. Bon voyage!