The Bare Bones: How to Plan a Trip When You Aren’t a Planner

Everyone has their own style of travel ranging from planning spreadsheets to day-of flight bookings.  But there are a few ‘must haves’ that even the most spontaneous of us cannot avoid eventually.

We need a who, a where, a when, and a what.  What you will do and eat and see can all be decided as you go, if you really hate planning.  But you really do need to decide:


Who you’re going with and/or who you’re going to see.  Are you going alone?  Did you talk your sisters into this trip?  College roommates?  Sending your parents?  Do you have local connections?  Friends to visit?

Trips cannot be planned with maybes.  You need committed people.  A struggle for millennials, to be sure, but trip planning cannot continue until you know the people involved.  The number controls things like rental cars and accommodations.  The people control things like where you go and what you do and how much you spend.  Really, the who makes the trip.  Makes it possible.  And makes what it is.

This trip to Chile was perfection.  Sisters and cousins, each with a ‘same age’ match, to visit the one living there.  With an even number we always had a walking buddy.


Where is almost always the easiest question to answer because travel inspiration floods our newsfeeds and our threads and our post vacation conversations.  Where I go depends on a lot on the answer to that Who question.   Last year I went to Florida and California to visit family and friends.  I also went to Quebec and Europe with friends and family because they were mutually desirable locations.  Traveling to people always tends to be a little cheaper than traveling with people.  Both have their perks, to be sure.

Post hiking photo in Tahoe, California.  Definitely a perk of this friend moving to the west coast.


I travel when I can.  Summer break.  Fall break.  Midwinter break.  But I’m an educator.  I don’t get to choose my days off.  But maybe you can.  You can plan perhaps around things like peak tourism (it’s best to go at the beginning or end of tourist seasons so everything is open but not as crowded), weather (if you want to see the northern lights in Iceland, it’s best to go in winter), festivals, or your mood.

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Trevi fountain with 1k people I don’t know.  Because I traveled during summer vacation.

Keep in mind, a local city can be explored in a day or weekend.  A stateside city in a long weekend (minimum 4 days to account for travel).  States or international destinations- a week to 10 days.  The more destinations, the longer the trip.  In my opinion.

But it’s also important to keep in perspective how long you can tolerate traveling.  I’ve found that everyone needs a down day about once a week.  If you are traveling longer, it helps to have several days where you know you can sleep in, have alone time, or have a flexible schedule.  Furthermore, some people need alone time every day.  If you are one of those people, don’t be afraid to take it!  We all need breaks and no one needs to be offended.  Especially since those little breaks help the group time go more smoothly.

Early flight, taxi nap, tour booking error to be ironed out = bad hair and tired eyes in the desert.



What you do, see, and eat.  What you spend.  What you sleep on.  This is the part you get to be the most flexible with.  

Every trip needs transportation, accommodations, and food.  It usually includes other things too like souvenirs, entrance fees, and accessory costs (if you need good hiking boots, for example).  But those are all decisions you get to make, when you want to make them.  The longer you wait, the more spontaneous you’ll become.

Cool medieval castle we toured in Switzerland.  Added it to our list day-of and got it all to ourselves to explore.

That said, I’ve learned you will also have to be all the more flexible.  It’s fine not to book tickets to museums ahead of time.  Unless the museum is notoriously booked out and it’s the primary reason you are going to said place.  Then you really ought to book the tickets.

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We missed out on touring this beauty because we didn’t get tickets in time.

And, that’s it!  If you can answer those wh- questions, you have yourself a trip!   The more confident and/or spontaneous you are, the fewer details you need in order to make the trip happen.


2 responses to “The Bare Bones: How to Plan a Trip When You Aren’t a Planner”

  1. […] week I blogged here about how to plan a trip if you aren’t a planner.  Back in March of 2015 I went to Ireland […]


  2. […] to plan a trip.  I discussed the essentials of trip planning in a ‘bare-bones’ post here.  Now, since I like to get a bit more organized with the ‘what’ of my trip, my […]


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