I am really lucky because I have a lot of longtime friends who still live close to me. I am also very lucky that my husband is so flexible about me traveling with friends. One more area of luck? I have a full handful of friends that I have traveled with in the past and come back liking them even more!
There are plenty of articles out there about choosing your traveling companions wisely and I could not agree more. On one of my recent trips, tension mounted consistently with one member of the travel posse and things literally came to blows. The rest of felt like we had to keep her safe as she drank a lot and wandered off on her own. That's not the kind of environment you ask for time off from work for! I have also had the experience of going away with someone and needing a good amount of space from them thereafter. Let's face it: some friends are great to meet for dinner but you couldn't spend a week with them.
Nothing brings out your friends flaws and annoying habits quicker than a week in confined quarters. Or, frankly, your own flaws and habits that other people have to deal with. Traveling helps you to learn about yourself but you also have to have some degree of insight about yourself before traveling with others. With one of my friends, we had a pre-travel meeting and talked about our fears of being together in a foreign country for two weeks. It helped us open the lines of communication to make a plan for how we would deal with certain situations if they came up. Most of the fears never came to fruition but it was a helpful and rather enlightening conversation, which I would recommend to others who are planning to head off on a journey together.
Despite the bad experiences, I have had many more positive ones. That was actually the point of this post! One of the girls I went to Spain with has been my friend since nursery school (amazing, right?). We haven't always been priorities in one anothers lives but we have been connected for that long and as life has evolved, we have grown closer and closer. Prior to Spain, we had only done a brief road trip and weekends away together so there was a lot to be determined during two weeks far away from home and unable to escape one another. It ended up being a great experience that only strengthened our friendship. We already have tickets to Costa Rica for November together! And we email almost daily (and while that isn't much different than before we traveled together, it's a huge testament to our appreciation for one another afterwards!).
So don't worry if you will run out of things to talk about; you won't. While all of the bad traits are amplified, so are all of the great traits. I think traveling with your friends is one of the healthiest, most fun things you can do for yourself and all of your relationships. Bon Voyage!