Planning Holidays When Your Life is One Long Holiday

Planning Holidays When Your Life is One Long Holiday

I should probably start by clarifying that our life is not actually one long holiday. Although we are away from our home country, Tristan and I are both working full-time jobs and endeavouring to live in Canada as locals. Of course, despite still needing to do all the mundane things you would when you are not on holiday – grocery shopping, renting an apartment, paying the bills, etc. – simply being away from “home” means it is nonetheless hard to kick that holiday feeling!

Unfortunately, this means we often forget to actually make the plans which are necessary for us to make the most of our time here and, to date, holidays and weekend trips away have been far less frequent than we would like. Indeed, since joining Tristan here in March this year, we have made just four short trips into the USA and have not managed to explore Canada beyond southern Ontario and its neighbouring province, Quebec.

After the recent Canadian Thanksgiving long weekend, we had a number of conversations about needing to make sure we planned “something” for the Christmas break – maybe a trip to the Caribbean, or maybe to Iceland (which is actually only a short international flight from Toronto), or at the very least a road trip somewhere out of Toronto. However, with our brains apparently permanently switched to holiday mode, week upon week crept past and before we knew it, we were a month out from Christmas having given no further direction to our holiday plans. With flight and accommodation costs continuing to increase, the prospect of a Christmas getaway was beginning to look unlikely.

Fortunately, my sister and brother-in-law decided that they would make an impromptu trip from Australia to visit us over the Christmas / New Year break. Being a good host means making sure your guests have a good time – it is this duty which served as the impetus for us to finally start planning an actual holiday. We got cracking… and, in a week’s time, we will be collecting our guests from the airport and travelling out to a little house near Niagara Falls to enjoy a few days away from Toronto and to host our very first Christmas dinner. That will be followed by a few days back in Toronto to share some of the more local places we have discovered over the last year, before we road trip up a few hours north-east to explore Ottawa and enjoy the New Year’s Eve celebrations.

Huzzah! Challenge ‘Plan Christmas Holiday 2016’ – COMPLETE.

Of course, this doesn’t change the fact that after this trip, we will probably still be languishing in this holiday / not holiday attitudinal limbo. We dread the thought of finding ourselves here again this time next year, having experienced little more of the world than we have today. In hope that we can avoid that, one of our resolutions for 2017 will be making sure we plan out our year in advance. We have talked for some time about making a list of all of the Ontario statutory holidays for the year and just locking in destinations for each. By mid-January, we will hopefully have our itinerary in place and will share it here on the blog so that you can all help hold us accountable!


– C

Have you lived, or are you currently living, overseas? If so, have you struggled with this lack of holiday planning inertia? We would love to hear how you have managed it because, frankly, we want need to do better! 

3 thoughts on “Planning Holidays When Your Life is One Long Holiday

  1. Based on what I’ve seen others go through, and our personal experience, the first year is just insane. By that I mean, it goes fast, is filled with confusion and paperwork, and depending on how you moved abroad, you may even have to start your savings again. Our first year we barely traveled. There was also just too much else to think about. So, this past year we were challenged by the #take12trips challenge. Another blogger created it and it’s just about getting out there (about once a month) and exploring something. It can be close and the next town over, it can be a neighboring province, or of course, abroad. But just pushing you to try something and experience a new place. We did it this year (I almost can’t even believe it!) and can’t wait to do it again next year!! So, basically, don’t feel bad about this year, just let it help motivate you for the next!


  2. Rather than plan places outside of Canada have you thought of ” digging deeper” into the place you live in? After all one wastes so much time in airports and hotel rooms it hardly matters where you are and a mall in Toronto is likely the same as a Mall in Iceland. Of course Iceland does have some unique geo thermal engineering projects which may be of interest.

    So my tip is to search out local community bodies that can give you insights into historical and political developments. Become an expert on the nuances of French Canadian politics including its unique view of multiculturalism.:-) check out local history libraries etc.are you doing language courses.? If so and your fellow students are on integration programs, you may be meeting an extraordinarily diverse group of people each with his or her own experience of Canada.

    I am not convinced about ex pat organisations.

    Be nice to refugees from the USA.


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