Dray Drinking Travel Tricks

Six Month Sabbatical Travel – Part One – Planning

What would you do if you had six months where you could work from anywhere in the world?

This is Part One of a three-part introductory series about the process of planning a six-month trip.

Part One: The Planning Process
Part Two: Decision Making
Part Three: Miles and Money

After ten years as an academic, I finally applied for and was granted my first sabbatical. The nature of my sabbatical proposal is such that I can do my work from anywhere in the world. I applied in September of 2016. My proposal was approved by the end of that year… for the spring semester of 2018 (essentially January 1st to early July). So I’ve had all of 2017 to (over)analyze how I would spend my time. Now, before you go on, take a minute and think about how you would spend six months if you could work from anywhere in the world…

It’s a great problem to have but not really an easy decision. Booking the typical 1-3 week vacation is pretty fun once you pick a general destination but the process for a longer trip is a bit more complicated. As a lover of lists and spreadsheets, I started to get organized and I created a set of guidelines for the places I would go. Here were my rules:

Good weather

This was a no-brainer to me. I don’t necessarily need warm and tropical the whole time but I don’t want to be anywhere during the winter or the rainy season. This rules out anything in the Northern Hemisphere north of Florida from January to March and most of the lower Southern Hemisphere during the American summer months.

Reliable Wi-Fi

As much as I’d love to completely unplug, I do still have work to do and I’m lucky enough that I love my job. Fortunately (or not), access to reliable Wi-Fi is less of an issue now, even in the most remote locations.

Reasonably affordable

There’s nothing worse than stressing about money so I don’t want to introduce that stress into an experience that should be so positive. Fortunately, in 2015, I began to really start to understand rewards points from credit cards, airlines, and hotels which will definitely help to keep costs down (see Part Three of this series to read about how I paid for all of this). That said, this rules out most of Western Europe especially during the summer months and potentially some other major metropolitan areas such as New York, Sydney, Tokyo, and others). Important in considering cost isn’t just the cost of housing, but also the cost of day-to-day expenses. Though I will try to eat in as much as possible, it remains likely that I’ll be eating out more than I normally would. These expenses can add up quickly!

Diverse Experiences

In other words, I don’t want to go to a resort for six months… I’d be bored out of my mind. I need to be experiencing new things to keep my mind stimulated. Of course, the appeal of each destination may vary. For example, you would go to Ecuador and the Galapagos Islands to experience nature but you might go to Japan to experience the fascinating Japanese history and culture. I’m open to both types of experiences… this is ultimately the beauty of traveling.

Easy to get around with just English

I spent four weeks in Seoul a few years ago staying outside the main tourist areas. It was a great experience to teach at a Korean university but the language barrier when I was away from the university was significant. You can’t fake Korean nor can you learn it in a matter of weeks. I found myself at restaurants pointing to other people’s food and to the beer in the refrigerator. It made me feel embarrassed and also a bit isolated. As I’ll be traveling solo for all/most of this journey, I need it to be somewhat easy to get around and have interesting conversations with people. I’d love to be multilingual but outside of some broken Spanish and a little Dutch, this just isn’t something I bring to the table.


I want to immerse myself in a place rather than just be a tourist and pop in and out. This means that, for the most part, I’d like to stay in a place for at least two weeks, preferably a month. That said, I also want to use this as an opportunity to see a variety of places. So that eliminates the idea of just living in one place.

So after I created these criteria, I went to work identifying places that qualified during the months of my travels. In the next part of this series, I’ll share with you my final decisions.

But I’m curious to hear from you. What are the most important criteria in selecting a long-term travel destination? What is your travel booking process like? Probably more spontaneity and fewer spreadsheets… but maybe not…

    4 Responses

  1. Can’t wait to travel vicariously with you Joris❤️

  2. I’ll be tracking your adventure. Enjoy the travels, soak in the experience, and take the roads less traveled. A little jealous! Toast to you!

  3. WEATHER is my number one concern when traveling. Good weather means lots of outdoor activities and happy people 🙂

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