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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.” Much of what I say below stems from a quote by my 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.

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

PS — Are You Booking a Trip Soon? Use My Booking Checklist!

These are the sites I use most to book my own trips. Using the links below is a great way to support Bon Traveler’s travel journalism at no extra cost to you. If you need help organizing your itinerary, get my free travel itinerary template here.

1. Book Your Flights

Use Skyscanner to find the best flights. It searches 100s of airlines and websites across the globe to ensure you’re not missing out on any route options or deals.

2. Book Your Accommodations

Use for hotels and guest houses. They have the biggest inventory and consistently offer the best rates.

3. Book Your Tours & Experiences

Use Viator or Get Your Guide to find the best tours and experiences. They are my favorite tour search engines. I always check both as their inventory varies depending on the destination.

4. Book Your Car

Use Discover Cars or to find the best car rental deals. I recommend comparing rental agency reviews on Google to ensure you are booking with the best company in that destination, as the reviews are often more accurate than the car rental search engines.

5. Don’t Forget Airport Lounge Access

Get a Priority Pass membership to gain access to 1,400+ VIP lounges and airport experiences worldwide. The Priority Pass app is the first thing I check when I have a layover. I’ve been a member for over a decade, and having a comfortable place to relax before and between flights makes air travel so much more enjoyable.

6. Don’t Forget Travel Insurance

I never leave the country without travel insurance. It provides comprehensive protection in case anything goes wrong (ie. illness, injury, theft, and cancelations, etc.). I use it frequently for my travels to stay protected.

My favorite companies that offer the best coverage and rates are:


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