Tim Foolery

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Trip Types? Short or Long?

I was recently catching up on a podcast from this spring (Happier with Gretchen Rubin) and one of the discussion points revolved around travel and the time to travel.  The hosts were talking about how sometimes it can be easier to take your vacation and not go anywhere because of all the time and effort it takes to properly plan a full week or two trip.  First off, I think that is crazy, but they did touch on a few good things.  Which is better? Several short trips (long weekends, 5 days away) or one long trip (2-3 weeks) each year.

A Shan woman in Myanmar

This Shan woman, wearing traditional clothing, sells spices and vegetables.

I work at a standard American company where employees get two weeks of vacation early in their tenure.  I’ve been there long enough now, I get four week.  While I have never, and can never see myself taking all four weeks at once, the question still holds true:  which do I prefer, spread those four weeks of time away over multiple trips throughout the year, or do I use it up on two two-week trips?

For me, an ideal option is to take a two week trip, then spread the remaining time throughout the year. Taking an extra day on a three-day holiday weekend, or creating my own three-to-four day holiday spreads the vacations.  I haven’t taken a full two weeks off in a few years now. Even our trip to Myanmar wasn’t quite two full weeks – you have to look back to 2016 for our last proper two week escape.

Part of the fun of the trip for me is to plan the trip. Let the excitement build while planning and then execute once you are there.  Some of the planning paralysis comes from people who think they need to see and do it all. They think they will likely never return to a place again.  I understand that, but I don’t buy into that logic.  I personally would rather leave a place wishing I had just one more day than the opposite wishing I had left the day prior.  You’ll never be able to do it all, so why set that outlandish expectation?

A five day trip can be perfect (including weekend days).  It allows you to break your routine, explore a new place, push your boundaries, but not have the stress of actually being gone for a long time.  Emails can wait, plan your projects and equip your co-workers with what they need to handle things in your brief absence and move on.

I always have another trip planned somewhere.  That’s one of the things that makes me feel fulfilled, always planning for the next adventure and if I took just one or two big trips a year, I fear I’d lose that feeling.  Next year, I’m going to try to push for a two-week trip intermixed with several long weekend trip.

What is your preference?  Would you rather just take a month off and escape, then have no real opportunity for additional trips?  Do you find travel planning daunting?


  1. Great post

  2. AJ says:

    I usually do one slightly longer trip of 9-10 days and then the rest are just long weekend types

    • Tim says:

      AJ – I think that’s a really great mix. Enough time to fully escape and relax, but not so long that you can only take one trip each year. The idea of going 50 weeks between getaways causes me so much angst!

  3. Ryan says:

    I’m with AJ – I usually do one longer trip, and then a few smaller ones as PTO/holidays allow. That said, I think if you have to spend a lot of time to get somewhere, you need to take more time. I live on the East Coast of the US, and I wouldn’t go to Asia for less than two weeks.

    • Tim says:

      I think this ratio is really the gold standard. I think it works so well, if you’ve got the time and to your point, aren’t spending 50% of that time traveling to the destination! Thanks for the feedback!

  4. hcyip says:

    I think your idea of a two-week trip and spreading out the remaining two weeks is good. I agree that it’s better to not want to cram too much stuff into a trip because there will always be another trip, another opportunity, etc.

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