Wayward Lovers

[wey-werd] turning or changing irregularly; irregular: a wayward breeze.

How to Travel in the Wayward Style

A question we get a lot is “how do you manage travelling so much?” I would like to answer this question in some detail. Perhaps to serve as a guide for people who have a similar work arrangement and priorities as John and I. Although, I do understand that the magic that has allowed John and I to travel is unique and rare and isn’t accessible to everyone. Anyways, here’s a glimpse into how we’ve made travel life work for us.

Big Picture Planning:

There are many wheels to turn while planning year long travel with many stops. Our general approach is to figure out a region, have a basic outline of where we want to go for as far ahead as we want to think, and then we start booking things around the three month mark. I’ve found if I start looking at Airbnbs earlier than three months ahead of when we want to arrive there tends to be not as many options. We try to book everything in unison … it’s a lot of back and forth between flights and availability of accommodations. Most of the time it’s better for us to have flights booked first and work out a place to stay around those dates. See below for specific tips about flights and Airbnb!


The main thing to note is John is working full time as a game developer with our companies Island of Doom Software and Handelabra Games. He gets to be his own boss and has the flexibility of being able to work around some weird hours. I can’t imagine sustaining this kind of travel without one or both of us having that regular and reliable income. I have worked remotely as a graphic designer in the past, but decided not to pursue anything in that field while travelling. I have been contemplating restarting my design career to travel with in the future.


A budget is so important to travelling … any kind of travel. So before we decided if we could make this epic trip work we sat down, made a spreadsheet, and figured out our expenses versus income. We figured out what we could spend on a daily average and what price range we could afford for accommodations. While we aren’t strict about our budget (logging all receipts and keeping an allowance) we have kept the budget in mind with all our spending.

It’s also important to be flexible with spending. For example, some cities are more expensive to live in, but we still wanted to go to them so to make it work we can either stay a shorter time, stay in a more basic apartment, or find a cheaper city to stay in during the next month to balance the spending. When we decided to go to London we found rentals to be super expensive so we stayed for a week instead of a month. In Dublin, another expensive city we stayed somewhere more basic. To make up for an expensive couple weeks of travelling faster and eating out a bunch during our trip with my brother and his girlfriend we opted for a budget friendly stay in Croatia. In general, it’s worth it for me to not stay in a shitty apartment for a month to make our budget work. I have such a better experience when I stay somewhere reasonably nice for shorter time or to make up for expensive places by going to a cheaper city/country later on.

In this same vein, we’ve also found going to places off season can save some money. Accommodations are cheaper, the cities are less busy, and there’s often discounts on tourist activities. You just have to be aware that some things close seasonally.


We’ve used Airbnb almost exclusively for our accommodations. We’ve found that there are two types of Airbnb places that we tend to use: one being a monthly rental, usually a place that is someone’s home that they rent out while they are travelling or that they have recently moved out of; the other being more traditional BnB-type places that are set up as either a room in someone’s home or a small apartment with minimal amenities. We occasionally opt for the second type for shorter stays, but generally we try to find the comfort of the first type when we stay somewhere for a month.

The main things we look for in an Airbnb is a monthly discount, good reviews (if there are no reviews we’ll send the host some messages), separate bedroom (most studio apartments make J+B go crazy), pictures available of bed, internet obvs., and locationLOCATIONlocation. I do a lot of research on neighbourhoods and transit options to find cool places to live in.

Some creature comforts we’ve found we like to have, but can live without: TV, laundry, dishwasher, microwave. When we have all of them in a place we’re living the dream, but we can also survive with none of them without much trouble.

Most places on Airbnb have weekly and monthly discounts that kick in at 7 days and 28 days respectively. If you enter in your dates with that in mind, you should see the discount and may find an expensive place turns into a reasonable place. Sometimes the discount % doesn’t show up, so you might need to do the math if Airbnb’s website is being weird. If a place doesn’t have a discount, or if you’re staying 27 days or something, message the host and they might make a deal!

After we move on from a place we always leave a review, and the host usually leaves us one. If you’ve got a good review history it’s easier to rent places, since potential hosts can look at your profile to decide whether to let you into their house or not.

If you haven’t used Airbnb before, visit with this referral link and we both get free credit!

Interlude – Travel in the New Style!


Here is another area that it helps to be flexible with. You can save many moneys by travelling on certain days. We’ve also been able to get cheaper flights by buying in bulk through sites like Air Treks or Indie Bootsnall. Sometimes it even helps to be flexible with where you want to go. Like when John and I decided to go to the Caribbean we realized not all island travel is created equal, some places like Martinique have super cheap flights from Europe while others don’t. So why not Martinique then! Google Flights lets you put in a region for your destination so you can explore the options.

Since most of our travel has been focused in Europe, we’ve found that once we’re there travel is easy and cheap … it’s not like flying in Canada. I’ve promised several first borns to be able to get from Halifax to Edmonton! In contrast we’ve flown from Rome to Edinburgh for under $100. Taking the train in Europe is a great option most of the time and there’s a lot of excellent info on The Man in Seat 61.


We choose where we go in a few different ways; one being places we’re interested in or places we’ve always dreamed of going to, places that we can get to in an easy/affordable way, and places where our friends live or we have some work conference to go to in a specific location.

I would say 90% of our travel is to places we are just interested in exploring which is anchored by the other 10% which is incorporating friends or conferences that have time/location constraints. Generally places we have obligations to are also places we want to go to anyways. The only place I wasn’t sure about was when we decided to spend a whole month in Birmingham, UK around a conference, but it ended up being one of my favourite places.


I am the worst at packing. I always come in just a hair under the weight allowance. Although, to my credit I’ve never had to open and reorganize my things at the airport because my bag was overweight. So maybe I’m actually amazing at packing?

Here’s my problem, we travel between hot and cold places so I need cold weather clothes AND summer clothes. I keep minimal shoes, but I still have four pairs (running, walking, flats, and sandals). To top it off my hobbies include art making and knitting! Not exactly the most compact of activities. At least yarn is light?

I have one medium sized checked bag and a medium sized carry on backpack plus my small day pack that I also carry on for flights. I organize all my clothes into transparent plastic garbage bags (1 for bottoms, 1 for tops, 1 for sweaters, and so on). My backpack has my computer, sketchbooks, and knitting. My daypack holds my camera and personal items and I hold it with the fierce clutch a mother has over her newborn babe.

John’s packing is pretty much the same, but he also brings some work-related items (test phones & tablets, weird computer cables, business cards, etc) and his squash racquet and gear. The all-important Apple TV with Netflix goes in his suitcase too. Somehow it all fits even after I sneak some of my personal items in his bag!


As much as I would like to not be a material girl, there are some things I just can’t live without while travelling. I will never make it as one of those cool backpacker chicks that only have one bag and can wear cargo shorts without looking dumb. My must travel with things are: camera, laptop, sketchbooks (yes more than one), markers/pens/pencils, watercolour set, knitting needles plus yarn, moisturizer, and an obscene amount of cardigans. Hey, that list wasn’t as bad as I thought!

For the laughs I would like to also share the list of things I thought I was going to need when I left Halifax for the first time. On top of my current essentials I also packed all my paintbrushes, a limited palette set of acrylic paints, and a portfolio book to hold all these paintings I planned to make (lol). These things made it around the world and were quickly ditched once I got back to Halifax. I did paint sometimes, but not enough to justify the luggage space needed for all my art junk.


If you’re like me and you like things then you also know the struggle of wanting souvenirs while travelling. I want knick-knacks for my imaginary mantle that I might have someday. However, I have to carry all knick-knacks, souvenirs, glass vases that I desire for possibly multiple months. I’ve imposed rules upon the souvenir type things I collect while travelling to avoid having to ship too many things home or breaking my back trying to carry multiple novelty salt and pepper shakers. Before I buy something I ask myself can I wear it? Is it light? Is it small? Will it cause me to throw something out of my suitcase? Is it consumable? Can I use it while travelling?

After going through my checklist the type of things I end up collecting are small art prints, postcards, jewellery, pins, and the occasional larger items like a mug or beer glass that we can use. Tote bags are perfect because they are generally useful and often have creative designs these days. To make up for the lack of knick-knacks I try to take many photos and make lots of sketches to remember my experiences better. I know this isn’t how to start a tiny bell collection, but I leave that for when I’m older and richer and I can hire minions to carry my things for me.


Anything we didn’t cover you want to know about? Send us a message or something and maybe we’ll write about it!