Yours truly, and my best friend Alessandra, trying to catch up on some Zzz's while on one of our numerous train commutes throughout Italy.
Yours truly, and my best friend Alessandra, trying to catch up on some Zzz’s while on one of our numerous train commutes throughout Italy.

Most of the time, I travel alone. I don’t go solo because I am antisocial or lack friends who appreciate traveling; rather, I often travel alone for several other reasons. Firstly, it is difficult enough to coordinate with the friends in my circle on what we want to do later this afternoon, so it makes sense that these same friends (whom I love dearly) and I make it difficult to plan anything more elaborate than a movie together. Also, though almost all my travels are pleasurable in some sense, work is always on my mind. I look at every experience as a future story that I can write about on this website, so my itinerary may differ greatly to a vacation that my friends might have expected. As a result, not only do I like to pack in a lot more sightseeing than perhaps my friends might, but I assume that I would prefer to spend my time in a local market or town square as opposed to relaxing on the beach.

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Though we may not see eye to eye on attractions within a travel itinerary, I still enjoy time spent with friends above almost all else. I’m sure most people share this sentiment, which is why we must find ways to coexist during our precious travels together. Also, as we get older, more often than not, opportunities to travel with friends become fewer and farther between; relocation, having children, and marriage don’t usually make it any easier to travel with friends (though they may make you want to escape with them more).

Choose Your Travel Companions Wisely

Before you even think about traveling with friends, you should definitely see if you have friends that you would be compatible to travel with in harmony. And if you have friends in mind for a trip, make sure that you can see yourself getting along with them in a mélange of situations. Many things can go wrong between friends, through petty bickering, lost patience, and so on. Compatibility is key, so keep in mind these few questions to ask yourself of your potential travel mate:

  1. Know them well? You should know your future travel partner well enough, which is relative, but you get the idea. It shouldn’t be someone you just met on the train during your daily commute, because you should be able to answer the following few questions about them.
  2. Same travel goals? Like I said in the first paragraph, I tend to have different plans when traveling than my friends might. However, the goals must not be completely divergent; if I want to write about the local culture while my buddy wants to hit the beach, either we should agree to spend time apart during the trip, have dedicated days for each of our whims, or not travel together – simple as that.
  3. Similar routines? It would be a disaster to try to go with a friend who wants to wake up at the crack o’ dawn for the sunrise, if you want to stay out and drink until nearly the same time. Usually, friends close enough to travel together share similar time schedules and routines, but it doesn’t hurt to be sure.
  4. Comparable comfort levels? Again, be sure that your goals are not dissimilar before traveling; Your buddy may be something of a thrill-seeker  and if you can’t stomach skydiving or scaling large mountains, then maybe this one isn’t the right person to go with.
  5. Can you talk? I mean can you guys really talk? Communication amongst yourselves is necessary, because with communication comes honesty – the more you talk about your likes and dislikes and feelings about different parts of the trip, the more you can tailor the trip to satisfy everybody involved. Furthermore, communication is just practical and good practice; why shouldn’t you be able to talk to your friend and seatmate on a long trans-Atlantic flight?
Waking up from an insufficient nap on a train; need coffee.
Waking up from an insufficient nap on a train; need coffee.


Compromise is the single most important factor to harmony and an amicable time together. In your daily lives, you don’t have to meet for dinner if the scheduling doesn’t suit you, but it is different when traveling together. You are traveling with each other to spend time together, so scheduling must work; going to different bars while vacationing together shouldn’t be the solution just because you each have varying tastes. With that being said, it is prudent to set some expectations you each have prior to the trip; this way, you are all aware of some of the things that are in store for you.


Sleep may be something that you plan on catching up on while on holiday, or, if you’re like me, it is the first thing to go out the window. But I’ve come to realize just how important sleep is. Just recently, I took a trip and had a mini reunion in Italy with some of my best friends, and sleep was the last thing on our minds. Towards the end of the trip, I felt myself getting snappy and crabby, and I could see that my friends were similarly getting cranky. Not good. Though you may not want to waste the precious little time that you are spending together, you will do more damage, possibly, if you get less-than-adequate sleep. Especially towards the end of your stay when you may be starting to feel the draining effects of your lack of sleep, it is important to avoid any discord that may follow your friendship back home with you. Read this guide on how to sleep well while traveling ->

Your Vices

You may have your addictions, caffeine and nicotine are two of mine. A vacation with friends is no time to quit! Traveling may have you more relaxed if you are sleeping more and working less, but traveling with friends means that you are in close proximity to them, probably more than you are back home. This means that you are more prone to getting irritable with them, and then it can snowball from there. I know that I require a large coffee within an hour of waking up each morning before I get a migraine, and Lord help my friends when I don’t.

I have found out that there ain’t no surer way to find out whether you like people or hate them than to travel with them. – Mark Twain


Need coffee, probably.
Need coffee, probably.

They say that you should never mix business with pleasure, and this is great advice for the most part. However, when traveling together, it can become difficult to split everything all the time. From before the trip even starts, when booking a flight or hotel, it is almost impossible to pay separately if you want to have any chance of being near each other, so one has to usually put up the money and swipe their card. It goes from there, throughout the trip, at restaurants, bars, attractions, etc.

A good system for this is to pool your money together into a shared wallet. Everybody pitches in equally, and trip expenses come out of that. This also is extremely helpful for those times paying at a restaurant; everybody’s tab can just be paid by the one person who is managing the pooled money, making it easier and less embarrassing when paying the bill than if everybody tries figuring out their own expenses.

Another thing to keep in mind regarding finances is that you should gauge each other’s financial attitude, preferably coming to a spoken conclusion before the trip (things can get messy if one of you thought something was implied). For example, you may be the budget traveler, and your friend might like to go eat well at fine dining establishments. You wouldn’t want to eat separately  would you? If you are the one that needs to be more frugal, then let it be known; and if you have any clue that your travel partner may be more strapped financially than yourself, try to be sensitive about it.

Split Up

Just because you are traveling together, it doesn’t mean that you should feel obligated to share every moment abroad with each other. If you have the urge to go somewhere alone, or if you just need to get away from your travel companion for a bit, by all means, do so! Do anything that will make sure that your friendship won’t get hurt in any scarring way. A little time apart, even if it may cause discomfort when you explain your reasons, will most likely be better in the long run for your friendship. Also, you multiply your chances of discovering something fun, which you can all go back to later and check out together.

Be Conscious and Responsible

Ultimately, everybody is responsible for their own actions and happiness. If you need to sleep so you don’t become cranky later, hit the sack. If you’re hungry and no one else is, grab a snack to tide you over, so you can maintain your energy levels. Be considerate, conscious of your attitude and sensitive to your friends’ reactions. Bite your tongue. 50-50 is impossible to maintain, as someone always falls short; strive to go above equal and to roll with the punches more, aim for slightly past the middle, and disharmony shouldn’t ever become an issue.

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Happily coexisting, New Years Eve.

I wrote this to address some issues that friends may have when traveling together, but this advice should be able to be applied to other situations, as well, such as traveling with family members or interacting with friends back home. Hope it helps on your next excursion, and may your friendships return with a bond stronger than when you left!

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