Dray Dreaming

FAQ: The 5 Most Common Questions I’ve Been Asked About My Trip


“Questions, I’ve got some questions
I want to know you
But what if I could ask you only one thing
Only this one time, what would you tell me”
Jack Johnson

After almost 7 months of traveling around (I extended my trip from the original 6-month itinerary), I’ve had countless conversations with people at home and abroad. Through these conversations, certain questions keep arising so I figured I’d take an opportunity to answer them since people seem to be curious. Plus, they’re good questions that I’d like to take some time to think about.

Question #1: Don’t you get bored?

I’ve been in some amazing places over the past few months so my immediate response to people when they ask this question is: “If I get bored, it’s really my own fault.” There are always undiscovered sites to see and always favorite places to go back to. In fact, my bigger problem has been that sometimes I wished I could’ve just stayed home and had a lazy day. Since I had to eat most of my meals out, this wasn’t really an option meaning that I was always out and about.

Of course, there were some nights when I felt a little bored. I’ve hardly had access to much TV and I’ve missed most of the major sporting events since the Super Bowl (except for the World Cup). Plus, given that I’m out during the day, I often don’t feel like going out again at night. My usual solution to this was to write for the blog, read a bit, or play some iPad games.

So, yes, there have been some nights when I’ve been bored… but not many… and certainly no more than I have when I’m at home.

Question #2: Don’t you get lonely?

Mostly, I’ve been happy traveling solo though I do feel lonely from time to time. So many selfies…

Questions about loneliness are somewhat related to questions about boredom. When you’re at home, the easy solution to your boredom is to call some friends and see if they want to meet up. While I’ve made some friends over the last few months, it’s not always easy to be so spontaneous. As a result, there have been some nights when I’ve been a bit lonely.

For me, two things defined these moments. First, sometimes I just missed my friends and family. FaceTime and WhatsApp help with this tremendously but they’re no replacement for being together. Second, the friendships I’ve made over the last few months have all been short-lived by virtue of my travel schedule. So it’s great to feel a close connection with someone new but it sucks to constantly have to say goodbye and start the search over again.

So, yes, there have been some times when I’ve felt lonely. However, in some ways, I expected to feel loneliness more frequently during this trip but it simply hasn’t happened. I think there are some misconceptions of loneliness and solo travel… which I’ll probably write about in a blog post soon!

Question #3: What’s been your favorite place?

So many beautiful places! How do you choose just one!?!

This one is probably the most common question and it’s absolutely impossible to answer. First, I really have enjoyed every stop on this journey… but in incredibly different ways. For example, it’s nearly impossible to compare Valencia and the Las Fallas festival to a chill little surfer town on the coast of Bali. Even comparing the two surfer towns I visited in Costa Rica and Bali is difficult given the cultural differences between the two places.

So, it’s a bit of a cop out to answer this way but I think my favorite place has been all of the places. In other words, I’ve loved the totality of the experience and the diversity of people and places that I’ve encountered.

Question #4: How did you pay for all of this?

I’ve written about this a couple of times before but I still get stunned reactions when I tell people that I have been able to travel for almost 7 months while spending only about US$5,000 on flights and lodging. Beyond those expenses, I specifically chose places that were more affordable (with a couple of exceptions) which also made day-to-day expenses fairly manageable. Further, some credit cards also provide status at some of the hotel chains. What this means is the occasional room upgrade and sometimes free breakfast as well which helps to save a few dollars/euros, especially in the more expensive cities on my trip like Amsterdam.

I had an Airbnb in Costa Rica, Budapest, and Bali which meant that I could have some food available at home too so I didn’t have to go out for all 3 meals each and every day. Finally, given that I was traveling so long, I had to resist the urge to shop since carrying around loads of souvenirs from each place was certainly going to be problematic. All of this planning helped to keep my overall spending at a reasonable level.

I certainly understand that most people don’t want to get into the credit card churning game. It’s time-consuming and there are definitely risks involved. However, I would not have been able to afford this trip without being able to pay with points. So, if you aspire to take an extended vacation or sabbatical at some point in your life, you must start thinking about how you’ll pay for it. The intuitive solution is simply to become an aggressive saver and/or find a new income stream. However, short of that, signing up for a credit card or two (or more) so that you can fly or stay for free can most certainly be worth it.

Question #5: Are you ready to go home?

I’ve obviously been getting questions like this more often recently as my trip winds down and up until a few days ago, my answer has been an immediate “no.” For most of this trip, I have been dreading the day it would all come to an end. However, I’m now less than a week away from returning home and for the first time, I feel excitement and maybe a little relief at the idea of being home. Living out of a suitcase is hard and even the most passionate travelers can get a little travel burnout.

I’m going to give myself a little pat on the back here for planning a good end to the trip. At the beginning of the trip, I had great energy for seeing and doing and having 3 months in Europe was a great way to spend that energy. My experience in Bali was designed to be a relaxing way to wind down when maybe my energy level was a bit diminished. And that’s exactly what happened… and maybe the diminished energy level is why I’m ready to be home and recharge a little bit.

Any other questions!?

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