Design or Destiny: How to Choose Travel Destinations

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This post about choosing travel destinations is sponsored by KAYAK. All musings and opinions are of The Professional Hobo

How do you choose travel destinations when the world is your oyster? Pick an activity you like and find all the places in the world to do it? Go wherever the flights are cheapest? Create a mission to visit all the “x” places in the world (such as wonders of the world)? Or just spin the globe with your eyes closed and drop your finger?

They say the world is small (and in many ways it is), but when it comes to choosing travel destinations, the world can suddenly appear very, very big, and the task very, very daunting.

Read on to discover how I choose my own travel destinations, with some advice for how you can do it too.

This post was originally published in 2016. It has since been updated for accuracy of links and content.


I’ve been lucky for the last 10+ years of my travel lifestyle. Only a few times have I been “stuck” for what to do next or where to go (For musings on one of these occasions, see: The Paralysis of Choice). For the most part, with a dose of patience and flexibility, my travel destinations have chosen me rather than the other way around.

For example, when I began my full-time travels, I had designs on Costa Rica, but for some reason couldn’t bring myself to book the ticket. This worked out well since an opportunity came up instead for me to spend the summer in the Rocky Mountains. After that, a volunteer/work-trade gig arose in Hawaii – a place I hadn’t really considered visiting, but one that ended up being serendipitous in a number of ways. Then it was a trip through SE Asia, then a sponsored trip in Australia, and then a tv show in New Zealand. And on and on it went.

It was much more by destiny than design that my travels have continued to evolve over the years. But I also believe that destiny is a moving target, and it’s important to continue to keep your eyes open for new opportunities. (See also: Destiny is a Direction)

Flexing the Plan

I met a girl the other day who is on an open-ended trip around the world. She has been in Peru almost two months, but only recently discovered (and fell in love with) the area where I’ve been living. She was complaining that she doesn’t want to move on in a few days as scheduled. I asked her if she has any solid plans or dates in her upcoming itinerary that curtails her flexibility – nothing. So I encouraged her to consider flexing her plan to take advantage of this place that has become special to her.

Some of the best travel plans are loose ones. Even with limited vacation time, packing too many things into your itinerary might mean missing some of the local gems that you couldn’t have anticipated or researched.

For example, during my recent trip to Ireland with Mum, we had an itinerary of places to stay, but we made sure not to commit to anything else. We had ideas, but no plans. This worked out fabulously; how could we have anticipated that our B&B host in Kilarney would give us such fabulous day-trip recommendations that we hadn’t considered? And if we had too many firm plans, we wouldn’t have been able to flex them to visit the seaside town of Doolin to meet and listen to an Irish musician my Mum knew through a friend.


Sometimes, despite our best intentions, a beacon of light doesn’t emerge from the sky with a glorious travel opportunity or other form of guidance that dictates our next travel destination. In this case, it’s time to design our destiny with some research.

The folks at KAYAK recently made me aware of their 2016 Summer Travel Hacker Guide and I spent quite some time browsing it.

They looked within their billion or so annual searches to give you, me, and other travelers wondering where to go this summer some solid recommendations. With top trending Summer Destinations, European Summer Destinations, Winter in Summer Destinations (for southern hemisphere locations), and Summer Friday Destinations (for weekend warriors), there is something for everybody on this list, with lots of food for thought.

For each destination, they list the best times to book airfare (and median costs), median hotel rates (and top trending hotels), and tips on what to expect at each destination (including average temperature and rainfall). And for Canadian readers who have suffered a hit on the value of the dollar, these guides can even help you maximize the low dollar by finding travel destinations where and when your money can go a little farther.

My own life and travel plans have been thrown into flux once again (more on this in another post), so I have personally enjoyed browsing the KAYAK 2016 Summer Travel Hacker Guide for inspiration of where to go next.

Where do you want to go this summer? And is design or destiny dictating your choice?

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4 thoughts on “Design or Destiny: How to Choose Travel Destinations”

  1. Most timely Nora, and indeed ever the dilemma – as I (blissfully) “struggle” with cobbling together a semblance of a “plan” to explore a goodly chunk of the Balkans and Turkey come Sept/Oct. Nothing will be nailed down in advance of course (even the rt. air will be via “standby” as an AA pilot chum has magnanimously offered me “buddy passes” from EC to Europe – how sweet is THAT?), but narrowing it (tentatively) down to at least what countries I might wander into is proving quite the challenge.

    Nonetheless, ’tis a most delicious dilemma to have. And not only do I enjoy the research (I mean, as you say – how sweet is it when you’ve arranged your life to allow the entire world to serve as your own personal oyster?), but wading through the many options can be very helpful.

    For example, while I am of course looking forward to exploring Croatia – I didn’t realize that Istria is apparently the TRUFFLE HUNTING capital of the world. As a serious hunter of wild edible shrooms years ago living in the U.S. Pacific Northwest (we’re talkin’ edible boletus mushrooms that you TRIP over with caps the size of DINNER PLATES), you can bet that I’ve now penciled in a few extra days to hunt down the legendary truffle!

    Then again, I’ve never been keen to slog my backpack from place to place for more than a month or two at a time. So even with unlimited time, I still have the dilemma of “do I slide into Macedonia and/or Albania and/or Kosovo and/or try to squeeze in Romania et al for a quick look-see?” or… stick to my favored slow travel style and limit myself to but Slovenia, Croatia and Turkey?

    Bottom line though – I’m a big believer in boatloads of research – all of which I toss to the 4 winds upon arrival. From there it’s all a matter of destiny and I let Ms. Serendipity lead the way!

    • Hi Dyanne!
      Ha ha – I hear you on all fronts! Tough decisions we have these days, huh? 😉 I’m a fan of a slow travel itinerary, but in short spurts, catching a few extra places/countries can be exhilarating as well.
      I’m not nearly as good in the research department as I suspect you are though…it’s a skill I could stand to improve on. 🙂

  2. So hard to answer that question. Just love the sensation of traveling, discovering new cultures… And it’s always really hard to find which destinations we ‘ll be going next times…


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