Part two of the travel planning series is how I decide where to travel to and easily the toughest challenge. The first part was how I find inspiration, which for me, is always a ton of fun. Making an actual decision is where you have to put some skin in the game and commit — and that can be tough in a world of what feels like endless options.

Travel Planning Part 2: How I Decide Where to Travel to

So for this part, I have a few tips and tricks for narrowing down from your “bucket list.” About two years ago I wrote a post titled, “Picking A Destination: More Than Where You Go.” It was inspired by favorite travel author, Alain de Botton who said this in his book “A Week at the Airport“:

Travel agents would be wiser to ask us what we hope to change about our lives rather than simply where we wish to go.

So as I share more about how I decide where to go, it really stems from this.

Travel Planning Part 2: How I Decide Where to Travel To

Asking myself the tough question, why?

It feels obvious and yet needed to be said. Why am I traveling to this place? Is it because I saw a pretty photo on Instagram or because I am genuinely interested in investing my time to be there? I try to take a step back and consider the reason behind why I’m considering a destination.

If I’m stuck between two places, this is a perfect time to ask “what would I like to change about my current life at home?”

This is my favorite question from Alain de Botton and it’s a game changer for how I decide where to travel to. I love going through the process of thinking about what am I currently craving to change at home. Perhaps I’d love to change my pace of life, so maybe an island destination would be better suited. Or perhaps I’m interested in introducing more design and art into my daily life, so a place like Copenhagen could be a great fit. I try to match what I like to change with what the destination offers.

Here is an example from when I was emailing with a friend who was considering Japan vs Portugal:

“Something I’ve been asking myself lately when I pick a destination, is “what do I want to change about my daily life at home?” For me, Lisbon is about slowing down, historic roots, cozy food and coastal summer. Tokyo, I find myself drawn to the design, the order, and precision — plus their ability to be committed to a craft and trade…”

Consider time of year factors.

Ever booked a trip to Southeast Asia and realized it was typhoon season? Yup. This is one lesson learned the hard way. Here’s timing considerations:

  • Seasonal weather
  • Peak season travel (this impacts cost)
  • National holidays (can affect openings of sights)
  • Big conferences (especially in major cities where this can affect accommodations).

Browse over flight schedules.

With some destinations having seasonal flights like Jackson Hole, Wyoming from San Francisco, it’s good to see if flights are available. I also get a good reference for pricing and helps me determine budget expectations.

Consider some parameters of the trip.

One other very important component is the parameters of the trip, like:

  • Do I have enough days to do the trip?
  • Is it in budget?
  • Does the flight time make sense for the amount of days on ground?
  • Does it conflict with schedules at home?

Where can my points get me?

My last tip for determining where to travel to next is considering where my points can get me. We often will plan a trip because we found some great deals with our points. I’ll give it a quick browse and determine if I can save some money on the flight portion of a trip.

You can find the full travel planning series here:

Part 1: How I find My Inspiration
Part 2: How I Decide Where to Travel to
Part 3: Planning the Itinerary
Part 4: When to Book What
Part 5: Tips for on Ground

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Travel Planning Part 2: How I Decide Where to Travel to



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