Mr. Always Write, Road Trip

Anyone who knows anything about Alexandra (The Little Things) and I knows that we are no strangers to hitting the road – whether to enjoy a local escape on any given day or a more adventurous road trip that takes us to parts of the continent we’ve yet to experience. This summer’s pinnacle is no different.

We’re fast approaching the start of our road trip, which has us slated to buckle up and begin our drive in the morning hours which are fast approaching, and we finally came to a crucial realization on the planning side of it all just a short while ago. Simply stated: There is no plan.

I’m not suggesting this is the way to treat every vacation, but we’ve often found that when it comes to our road trips we’ve had a lot of success in approaching them in this manner. Beyond that, we’ve had a lot of fun doing it this way. Given the nature of all that this particular trip would entail and the lengths that we plan to travel, we certainly set out with every intention on planning it through and through. However, every time we tried to begin to put pen to paper to create a schedule we noticed that it continually made us feel restricted, anxious, and overwhelmed. So, we decided to trade in the hourly itinerary for a synopsis instead. One that would set us up for an adventure we’ve very much looked forward to for months now, with the most liberating of plans (or lack there of) in place as we embark upon it.

Alex and I are pretty balanced and logical thinkers. We know when a plan is best and when we can get away with winging it. My goal here isn’t to advocate being ill-prepared or unorganized where diligence would be a more effective approach, but rather to highlight the fact that there are various paths towards any destination. It’s up to those involved to know what works for them and to put what’s necessary into motion. As we began to crack open the books on what else we may encounter on our roadie, we kept realizing there may be more we wanted to do, see, and explore on this journey. Instead of feeling limited along an otherwise open-ended type of path, it made the most sense to be true to the whole concept of the road trip and make ourselves readily available to experience whatever we choose to (whenever we feel like it).

There are definitely going to be varying opinions on our approach, so rather than seem as though I’m at one extreme of it all (with no sense of all sides) I wanted to be as objective as possible and lay it all out there. Here’s how we see it:


  • Freedom to drive as much or as little as we choose for any given time period.
  • Open to stay longer somewhere we’re enjoying or leave sooner than expected if we want to keep moving.
  • Not limited to the cities we choose to see, explore, or stay in.


  • We won’t be as familiar with the areas we plan to visit, without having researched them in advance.
  • Vacancy may be an issue we have to face when finding lodging.
  • Difficult to budget effectively without having the information needed to consider all potential costs.

What we know for sure:

  • We have 11 vacation days to utilize throughout this trip.
  • Our main goal is to drive from Oakville, Ontario to Charlottetown, Prince Edward Island.
  • We will be splitting up the road trip into various day both getting to PEI and then on our way home, too.
  • Our path has us driving through Ontario, Quebec, New Brunswick, Prince Edward Island, and Nova Scotia.
  • We will be staying overnight in a number of places and plan to do so where we’d like to explore a little more.

Want to know something else we’re pretty excited about? We’ve collaborated with 2 great brands, both of which we’re actual customers of on a regular basis, who have jumped on board to support us throughout our trip. Petro-Canada and freshii have been generous enough to fuel us along the way! (In their own respective ways, of course.) We couldn’t be happier that these companies have shown intrigue in what we’re doing and we look forward to supporting them in-kind the whole way through. Why wouldn’t we be pumped about sharing our epic Canadian adventure with these amazing Canadian brands?

Our Connection to These Brands

Petro-Canada: Alexandra and I are avid point collectors. We used to be loyal to another gas station, because of the affiliated rewards program, but then stopped months ago once we realized how little those hard earned dollars were actually going as far as point collecting was going with that network. Our search for a new pump to frequent was a quick one, as we wanted to ensure we chose one that would be easy to find and had perks we could actually brag about. In came Petro-Canada and the rest is history. We’ve already accumulated more points, which allow us to get more free stuff that we’ll actually use, in far less time!

freshii: Along a major route into and out of our area of Oakville, we noticed freshii when we had first moved in. We were both aware of the brand, but were naive to all it entailed. So, we gave it a try one day and we’ve never looked back! Their name says it all, as you know you’re getting good ingredients and a great meal. They have a perfect selection of options and are always doing new and innovative things to keep their customers happy and well fed. As a bonus, they have a reward program too – just make sure you download their app and start pre-ordering today!

So, that’s the plan (so to speak).


P.S. Want to join us on our journey? We’ll be using #PPSxMAWxPEI along the way, so feel free to check out whatever we may be up to whenever you’d like on Facebook, Twitter, or Instagram.

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Shaun 💬
Freelance thinker, marketer, and writer. Oxford comma enthusiast. Spider-Man supporter. Hockey fan, with two favourite teams. #ProgressYourPresence