Dray Dreaming

Picking Places: To Visit or Revisit

Bali Sunset

“Nothing much could happen
Nothing we can’t shake
Oh we’re absolute beginners
With nothing much at stake”
David Bowie

Picking your next travel destination is hard. Ironically, I think the stress of the decision is so paralyzing that it actually causes some people not to travel… or at least delay booking their next trip.

For many of us, we’re lucky enough to have had a great time on vacation at some point in our lives whether that’s some extravagant international adventure or a quick weekend roadtrip. There’s something wonderful about getting away from the day-to-day grind and each of us has our own way of doing it. But how do you pick the next place? On the one hand, you know you’ve had a great time at a previous destination… but, on the other hand, you want to experience something new.

Decisions decisions decisions!!!

The Case for Going Back

It’s been almost eight years since I moved to Philadelphia and I can still remember my first summer so very clearly. I decided for that year, I wouldn’t travel and would instead stay and immerse myself in my new city. It was a beautiful Friday night in early June and I walked into my favorite bar expecting it to be energized and packed full of people. Instead, there were four other guys sitting at the bar and one bartender on duty. I gave a confused look to the bartender and she said “Oh… you haven’t spent a summer in Philly, have you?” She explained that between Memorial Day and Labor Day, the entire city basically migrates to the Jersey Shore on the weekends and that despite the warm weather, summertime was downtime for bars and restaurants.

Over the months and years that have followed, I’ve asked many people born and/or raised around Philly about this phenomenon and they all described a comfort of doing something fun with people they’ve been going with for years (decades in many cases). Many of those people use the majority of their vacation days extending various weekends throughout the summer. To be honest, at first I was really critical of this because I felt like (A) it seemed like a lot of work to do the same road trip every weekend all summer long and (B) it lacked adventure.

However, as I thought about it more, I began to understand. It’s great to get away and if you know you’re going to have fun in a place that you know and love with people that you know and love, what could be better? True, it’s not necessarily as adventurous but you could certainly make an argument that wandering alone for weeks through a foreign country is a less appealing option.

The New York Times just re-ran an article from 2012 about how hard it is to make and maintain friendships in your 30s and beyond. Based on the article, it would seem that experiences like regular weekends away are vital in creating and maintaining these connections. So I certainly can’t blame anyone for planning their vacation time around cementing those relationships whether it’s weekends at the Jersey Shore or some tried-and-true vacation destination where family and friends reunite.

Connecting with friends and family is a strong reason for picking a familiar destination but what if you’ve traveled somewhere and just loved the place so much that you wanted to go back? Besides going back to Holland to visit my family, I revisited my first destination a few years ago. I had gone to Barcelona once before and just found the city completely mesmerizing. While I lacked the courage to spontaneously relocate, a few years later I found a cheap flight and a cheap hotel and decided to go back. I just felt a connection to the place. There was an energy there that resonated with me. The beach. The people. The music. The colors. The architecture. The food. I loved all of it!

So I went back and loved it just the same… but I had a completely different experience in Round 2. In Round 1, I was anxious to be a tourist, to discover everything that makes Barcelona such an iconic tourist destination. In Round 2, I somewhat arrogantly felt more like a local (despite not speaking the language or knowing anything beyond the popular tourist sites). I stayed in a different part of the city and felt no urgency to see anything. Instead, I just wandered. I didn’t visit a single museum but instead would try to find a nice café to read and people-watch. Or I’d try to find some local hole-in-the-wall bar or restaurant in a non-touristy neighborhood. It was only a week but I felt like I got to know the city in a completely different way. Instead of building connections to people, it connected me even more to the city and I’m sure I’ll go back again. In the words of Marcel Proust, “The real voyage of discovery consists not in seeking new landscapes, but in having new eyes.”


The bright colors and delicious food are just part of why I love Barcelona so much!

The Case for Picking Someplace New

But some are true adventurers and refuse to go back to the same place twice because they long for novel experiences. There is of course real value in immersing yourself in the unfamiliar. For example, you may realize you like something that you didn’t know you liked, whether that’s food, music, art, architecture, culture, or something else. Think about your favorite musician. At some point, you had to give that band a chance without knowing if you’d like them or not.

Imagine the hole you’d have in your life without that music. Or imagine if you never tried pizza. Or saw your favorite movie. You’d have missed out on so much joy because you didn’t try something new. Those same holes exist based on some other thing we haven’t experienced before… we just don’t know it yet. We should all be aggressive in trying to fill those holes by trying new things. Plus, even if you try it and you find you don’t like it, you’ll learn something new and be better for knowing.

How Do You Decide?

I’m going to try to avoid talking about work in this blog but I teach classes on sport analytics and this is a classic case of probability and risk. Take two oversimplified options:

  1. There’s only a 1% chance you will have a bad time but less than a 40% chance that you’ll have a truly unforgettable experience.
  2. There’s a 10% chance you will have a bad time but more than a 60% chance that you’ll have a truly unforgettable experience.

There’s no wrong answer here but your preference would lead you to make very different decisions. When you go to the Jersey Shore, you know with a high degree of certainty that you are going to have a good time but after a certain point, the weekends become less distinctive because you’ve done it all before. If you pick Option #2, there is absolutely a greater chance that you won’t enjoy the experience for any number of reasons but there is also a greater chance that you’ll forever be telling stories about that time you were in _______.

Of course, this scenario is oversimplified. Picking Option #1 can be more adventurous by changing the manner in which you experience a familiar place. You can also make Option #2 a safer option based on the destination and experience you choose.

My Struggle to Decide

So on my current sabbatical, I’m split about 50/50 with destinations old and new and I struggled mightily making my choices. Currently, I’m in Costa Rica, where I was only a year ago. I’m exploring a completely different part of the country and living here for a month rather than bouncing from place to place over two weeks like a typical tourist. So, I feel some novelty even though there’s comfort in this place I know. Could I have spent this time exploring something more adventurous? Absolutely! But no regrets… so far (though as of this writing, I’ve only been here a few days).

At the end of this trip, I’ll return to Bali for several weeks. Much like Barcelona, I fell in love with Bali a few years ago and couldn’t wait to return basically from the moment I left. I have no agenda upon my return. I just want to be there. I realize that there are other places I could visit… and I’ll get to those eventually. But for now, Bali is where I want to go.

Bali Rice Fields
I mean, how could I NOT want to go back to Bali!?!

Besides those two places and a return trip to Holland where I was born and still have family, every other destination is new to me and I’m every bit as excited to experience those destinations as I am to return to Bali.

Final Thought

I think Robert Louis Stevenson described travel nicely when he said, “I travel not to go anywhere, but to go. I travel for travel’s sake. The great affair is to move.” In other words, there’s no right or wrong answer… just go!! Because in the end, no matter where we go, “we’re absolute beginners, with nothing much at stake.”

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