What I’ve Learned from Traveling with Friends

*I actually drafted this post about a week ago and then saw this Vogue article in the Girls Night In newsletter last Friday–it touches on a lot of the same topics and may be helpful, so I thought I’d include it here! 

I feel super fortunate that my group of college girlfriends has made such an effort to travel together over the years. We all live in different parts of the country and have different work/school schedules, but we try to do a couple of trips every year so that we can all see each other in some combination!

We’ve been lucky that we’re all pretty agreeable and mostly interested in doing the same things, which makes it easy to plan in advance. However, having dealt with different situations and traveled to a few different places, we’ve had to make decisions as a group that were either no-brainers or slightly stressful! As a result, here are a few things to think about before going on a trip with friends…


What will you do if someone backs out of the trip last minute? We’ve decided that going forward, it’s best to figure out a “policy” in advance so that there are no misunderstandings should someone’s plans change. Will they eat their cost, will the remainder of the group cover for them, or will you try to book new accommodations that work better for a smaller group? These types of situations can get awkward really quickly if there’s no rule in place, and people have different preferences as to how they’d like to handle cancellations, so it’s best to work something out within your group before these types of issues emerge. Things happen, and being a good friend is more important than fussing about money, but everyone is in different life situations and what one person sees as fair or right may not seem that way across the board.

Is planning ahead welcomed or annoying? Usually, when I travel with my family, we basically make zero plans or reservations, we just go into the trip with a list of activities/must-sees and then decide what makes the most sense to do each day once we get there. However, when my friends and I were getting ready to go to Savannah, I had done lots of online research and collected recs from locals, so I knew of a few restaurants I wanted to try while we were there and also knew that making reservations in advance would be key. Thankfully, my friends saw this as super helpful–many of them were extremely busy leading up to the trip and had zero time to think about logistics–but I’m sure it could also come across as controlling depending on the group. For us, though, it ended up working out really well! We had some structure to our days but also had enough flexibility to schedule other things as we learned about them (like our awesome pedal pub ride), and we got to take advantage of trying some delicious places and go on a cool ghost tour thanks to doing a little legwork beforehand.

How can you compromise? Maybe you’re itching to try a certain restaurant but other people don’t want to pay $30+ for an entree when you’re going out to eat several nights in a row. Look at brunch or lunch menus; they’re often cheaper and you can still get the same experience without paying a price that not everyone is thrilled about. When you’re with a group, you’re always going to want to have several options, just because not everyone is always going to share the same opinion, no matter how close you are!

Can you coordinate your schedules? Traveling to and from the airport and checking in/out of an Airbnb is that much easier when there’s at least one other person with you. Of course, sometimes people need to arrive or leave at times that may not be as ideal for the rest of the group, but comparing flights beforehand will ensure that there’s no confusion–or frustration over a high Uber fee–the day of!

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