Travels With Sister: Three Lessons

It’s hard to find a good travel companion– one reason I prefer traveling alone is that it removes the stress of obligation, of potentially incompatible travel styles.

But there’s one person I would travel with all the time if I could: my little sister, Hillary.

Hillary and I grew up taking trips with our parents, but it wasn’t until our backpacking trip during summer 2011 that we realized how much we loved traveling together.

It helps that our travel personalities are compatible. I love researching and planning trips, while Hillary prefers going with the flow. So I made our itinerary and Hillary enthusiastically went with it. We both like walking for hours and taking tons of pictures and going to museums and eating well. We never got sick of each other’s company– except when we did, and we easily took a break from each other.

After that trip, Hillary moved into my Somerville apartment for the rest of the summer, and we continued engaging our travel spirit on long bike adventures around Boston. It wasn’t Europe, but there’s nothing quite like getting chased by wild turkeys in the glorious Mt Auburn Cemetery– an adventure that can only happen in Cambridge.

I love traveling solo– it’s empowering — but often I wish Hillary was with me, so she could enjoy all the things I’m experiencing. I feel it most strongly in these delicious, colorful places I find myself in– like Malaysia or Georgia — where I know Hillary would be as giddy as me. Also, Hillary takes better pictures of me and models in better pictures FOR me than anyone I know. There’s a whole photographic experience missing from my travels without her.

At some point this summer, we’ll be back together for some adventures in the USA. There’s a specific trip (to be revealed later) that we’ve been talking about for over a year, and we’re dying to put the inspiration from our Pinterest board into action.  (Not-so-)Secretly, I’d like to take a few big trips with her again someday soon– perhaps Thailand, maybe Mexico. For now, those plans are only in the dreaming stage… but we’re oh-so-good at dreaming.

In honor of Hillary, here are three things I learned from backpacking with my sister. These are lessons that can apply to anyone you travel with!

1. Play to your strengths.

In the months before our backpacking trip, while Hillary was studying in Barcelona and I was working in Boston, I started researching locations and mapping out a rough itinerary. I kept asking Hillary to do some research, tell me what she was interested in, be engaged. Except for a couple of suggestions (“I want to go to Istanbul,” “Plitvice… whoaaa… is that photoshopped?”), she didn’t. Not a smidge of research.

On the other hand, at one point before our trip, Hillary got upset with me for monopolizing the decision-making about our trip. She didn’t like that I was so insistent about going to Croatia, and she wanted to make sure she would get her say.

So what happened? Well, we had a fantastic trip that we were both very pleased with and that we both gush about to this day. And what we learned was that Hillary hates doing research and planning trips, and I love it. I couldn’t be upset with her for refusing to plan, and she couldn’t be upset with me for doing the planning. Recognizing what we both liked to do and what we were good at resulted in a trip we both enjoyed—during and before.

2. Deal with little problems before they become big problems.

Hillary and I had a few games we liked to play when we were traveling together to pass the time on long bus rides or in midday cafes. The first was GHOST (a description of which can be found here). This was a perfect game for buses, since you don’t need anything besides an optional pen and paper, but once we started bickering over the game, we stopped playing. The next was the card game Rummy, which we played obsessively. We kept score in my notebook to figure out who accumulated 500 points first. But once we started arguing over the point-keeping, we decided to stop playing scored rounds—it wasn’t worth fighting over something as trivial as a card game when we were traveling together. These examples might seem like simple sisterly disagreements, and they were—but since we would be spending almost all our time together for six weeks, it was important to stop the little problems before they became larger. Don’t let little disagreements fester—acknowledge them, address them, and deal with them. You’ll be happier later.

3. It’s okay to take a break from each other.

Hillary and I love spending time together, but we still had our personal moments. When we were in Split, Croatia, Hillary wasn’t feeling well, so she stayed in the hostel to sleep while I went out to explore the city on my own. When we were in Sarajevo, I wanted some time to myself to read The Brothers Karamazov, so Hillary went off on her own and ended up having a long, hilarious conversation with the only other person staying in our hostel—an American named North who was studying fisheries in the land-locked country of Bosnia. (Everything about Sarajevo was bizarre for us.) The result of these little independent excursions was that we actually had stories for each other—and we got some much-needed alone time. It allowed us to enjoy our time together even more.

I can’t wait until I’m able to travel with my sister again, and have more wild and wonderful adventures with my favorite person in the world. Soon, someday soon. We never stay apart for long.