3 Reasons to Just 'Wing It" on Your Next Trip


A shot of me in Iceland. Fun Fact: I could have sat here all day.

I’ll be honest with you, I am not a very experienced traveller. Last June I went on my first trip in 10 years and it was my first trip ever crossing the ocean!


I booked my boyfriend and I plane tickets on a whim in December 2017.  We’d talked about the idea of going to Iceland for over a year so one day while he was in the shower I thought “f*ck it!” and I hopped online and booked us a flight for June 2018.  Now, keep in mind I literally booked us a one way ticket to somewhere we had never been before 6 months in advance.  Why?  Because that’s how I was able to afford it!

Now, we clearly had lots of time to actually PLAN out every minute of our trip.  We, however, decided to just see where life took us instead and I’m so glad we did that.


Here’s why:


1. Pressure Free Schedule

Our flight left Toronto, Ontario around 7:30pm and we landed in Iceland around 5:40am.  My plan leading up to the trip was to land, pick up our car rental for 7:00am, and immediately start driving around and exploring until we could check into our AirBnb at 3:00pm.  This was really the only plan I made, and guess what?  It didn’t really happen like that.

Teagan (@teaganpaintsthings) on top of the world in Iceland.

We landed, got through customs, I threw up from a raging headache, we sat on the airport floor for about an hour, and then we went to meet with our shuttle driver to take us to the car rental agency.  After we got our car, we immediately found a place to take a nap.  In my mind, we’d sleep on the flight over and be good to go for the day.  WRONG.  Turns out planes are scary and our plane was particularly small and didn’t really offer a “sleep through the night” type of set up so we were exhausted.


We actually ended up driving to our AirBnb, parking out front, and sleeping in the car for a couple of hours.  I ended up contacting our awesome Airbnb host and he allowed us to check into a different room early.  So we napped again.  By the time we were ready to start our day, it was late afternoon.  We ended up driving to Reykjavik and just wandering around for the remainder of the day which was awesome!

I can’t imagine if we’d made actual plans to do stuff that day.  We would have straight up crashed the damn car from exhaustion!


2.  No Plans = No Disappointments

Now I’m not suggesting that you just blindly go on a trip without any research of that place.  Iceland has a LOT to offer in the looks department and so we did each have one specific location that we wanted to see while we were there.  We understood that these plans were loose so if we didn’t make it to those locations we wouldn’t be upset.


We did end up going to both of locations we wanted to see and we were really able to take our time getting there and just enjoying it while we were there!  I’ve heard of so many people planning to do all of these things and then they end up running out of time and miss something or they just aren’t able to really take anything in and enjoy it because they’re so concerned about getting to their next location.

Pick a couple of things you’d really like to see, and then enjoy other things you may encounter on the way to those locations!


3.  Extended Trip Availability

Because we booked so early and we only booked a one way ticket, we were able to think on other things we may want to see.  Travel within Europe is very affordable so we were in a position to think about possible visiting other countries.  Obviously this depends on your employment situation but you can work around this slightly!  I had booked 2 weeks off of work, even though I knew we were only going to be in Iceland for 4 days.  We ended up popping over to England to visit some friends for a few days before we came home.


Fact: Every small village in England is perfect.

We did have all of our flights booked by mid May, so we were at least prepared in that aspect.  You probably could just go in blindly and purchase flights as you go, however this can be pricier than booking in advance and countries often don’t like when travellers come in without any real plans to leave so I recommend purchasing flights in advance.

Long story short, if we would have planned out every single minute of our trip, we would have been incredibly disappointed.  Not only would we likely not have seen everything we wanted to, but we wouldn’t have had the opportunity to take our time and truly enjoy our time away!  Not to mention, we would have been so frickin’ tired from not allowing ourselves to rest and go at our own pace.


Next time you travel, I really do recommend just winging the minor details.  Pre-book your flights, pre-book your accommodations, but just explore and see what kind of things you find as you go!

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©2020 Jessi McConnell | Jess the Snapper  |  @jessthesnapper