Eventually You Have To

I can’t imagine how anyone does all this digital nomad trip planning on their own. Independently of all this organizational mayhem, we decide we’re going to Oktoberfest.

What if we book a one-way ticket? Then we don’t have much choice, do we?

We’re going to Munich for the first of October and we’re flying out of the Toronto so we need to get there before we go. This will force us to see some friends and family before we’re off.

Time to hunker down…

We start making bits of progress by going through the closets here or there.

We rake through our wardrobes. I try everything on. Do I love this? Do I really need it? Would I miss it? Jenny hosts a few clothing swaps with friends. Buckets of clothes are donated.

Small home improvements are made that we want out of the way. No future tenants of ours will have anything to complain about in a year’s time. Shower door edging. Closet rails. Dishwasher maintenance. Drains snaked. Check.

It’s not much but it’s progress. Progress feels good.

Crazy? Don’t forget about all those circled Schengen areas!

Lists are assembled. Spreadsheets are created. By July our glassed in second bedroom has become a whiteboard.

There is so much to see in this world. Where the hell are we going to go?

From spring to early summer, I put no fewer than fifty things on Craigslist. Gore-tex jackets I don’t need. Couches. Record Players. Knives. You name it, I’ve sold it on CL.

Jenny put probably two or three hundred small things on Bunz — a service that lets you trade goods instead of cash. Stuff we figured we couldn’t get much for.

Hey, we’ll take consumables like a loaf of homemade bread, kimchi or a bottle of wine. If you want our old flower pots, shoes or poker sets.

First Stop Munich

The start date is set. We’ll lose money by backing out now. After Munich, then what?

Jenny’s company isn’t asynchronous. She may be a remote worker, but the majority of the company lives and works within North American time zones.

They still have meetings and things that require discussion, in person. We’re the ones travelling, not her co-workers. It’s on her to be accommodating. If we’re in South-East Asia, that could mean working til 1AM or getting up at 4AM.

I will still have to do some video calls with online clients. Ideally at reasonable hours for both parties.

I have to remind anyone we’ve told so far that this isn’t a vacation. It’s long-term travel but we’re working. We aren’t planning to hang out on the beach, drinking Mai Tai’s and hitting up tourist destinations all day, every day. Yes it’s exciting, but it’s also a delicate balancing act. We need to make sure we do this right because we need an income to do it at all.

After Munich we’d like to go and see some friends in Bordeaux that we haven’t seen in years. We’ve been meaning to go for ages so we reach out. They graciously offer us a spare room, but we don’t want to overstay our welcome. Lets keep it to a week.

The train from Munich to Bordeaux is a bit longer than I’m willing to commit to. What if we spend the weekend in Paris. People do that right?

OK. 3 stops and 2 weeks down. 50 more weeks to plan for!

There are 60+ countries on our list of places to visit. We can’t visit them all in a year and still get shit done. We’re going to have to think this through.

We’re overwhelmed by our options and aware of our Canadian visa limitations. I propose that we start rating places on a scale of 1–10. 10 is a, “must-go Bucket List item,” 1 is a, “it’d be nice but I’m not dying over it.”

That won’t necessarily work though. We have to budget for the cost of living appropriately. Scandinavia or the UK are expensive. Thailand or Vietnam, not so much.

What about the weather? We can’t lug around clothes for all four seasons. You can make a list of countries but being in Italy doesn’t mean you can see everything you want to see in Italy. You’re going to have to make concessions.

Don’t forget about overstaying your welcome. You can spend six months a year in Ireland, the UK, or even in South Korea on a Canadian Passport.

The rest of the EU? A whopping 90 days within 180 days. WTF? That’s 22 countries on one typical on-arrival tourist visa!

Why is it that even within the commonwealth you need to apply for a visa to go to Australia? It’s easy to obtain, but still?

These are all considerations we have to make.

Previous experience tells us working in South-East Asia or Australia will be difficult. Unless we want to be Vampires and sleep during the day, these might have to be ‘vacation days.’ We should limit the time we spend there.

Organized Chaos. Does this make sense to you at all?

We cave. We have a rough idea but we can’t decide. It’s time to bring a third party for this decision. We bite the bullet and go to a flight centre. This is atypical for us but we’re stumped. What itinerary can they give us that will:

A) Make some tough decisions for us. I asked for 3 options. 20x fewer decisions than the countries we want to visit.

B) Save us a little money compared to booking each flight ourselves.

If you know anything about me, you know I’m a tiny bit stubborn. I like doing things myself. I have never booked travel through a travel centre before. Ever. I won’t even willingly travel to all inclusive resorts.

It took a lot of stress to resort to this and it removed twice as much stress in response. This could be a sign of a change.

All the options were good but we settled on one.

It’s Not the Entire Year Yet

It takes us through February of 2019.

We’ll have more planning to do while we’re travelling. A month in a few places should free up time to work. This opens up some weekend excursions too. We need some spontaneous flexibility.

We’re following the weather and good flights. Here’s the itinerary we settle on:

  • October 1–5 — Munich
  • October 5–8 — Paris
  • October 8–14 — Bordeaux
  • October 14-November 11 — Florence
  • November 11–14 — Rome
  • November 14-December 17 — Malta
  • December 17–27 — Vietnam
  • December 27-January 15 — Thailand
  • January 15–30 — Melbourne
  • Back to Vancouver
  • To be determined…