What an Upscale Digital Nomad Itinerary Looks Like

Once we let the world know our intentions to become upscale digital nomads we got so many well-wishes – and also a million questions.

But the two questions we’ve heard over and over are ‘where are you going to live?’ and ‘What is your itinerary?’

The answers to these very reasonable questions are both simple and totally complicated.

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Where are you going!?

We’re not really going anywhere. Our intention is to not live anywhere, but instead to live – um…anywhere. So I guess we ARE going anywhere after all. See: confusing!

But the point is that we’re not on this journey with the intention of becoming ex-pats somewhere.

Our intention is to find really cool affordable upscale travel destinations to spend some time.

Then, when we are done there or get bored, finding another cool affordable upscale travel destination to spend some time.

How long at each cool place? Depends on how long it takes for us to be done with a place!

As avid luxury travelers our whole lives and particularly in our relationship, one of our greatest frustrations about ‘vacation’ has always been meeting people somewhere cool in the world and them saying something like ‘You know where you REALLY must go? Bansko, Bulgaria!’

We would always look at each other and say, ‘YES!’ but knew in our brains that we had to go back to day jobs and maybe (MAYBE!) one day we would go to Bansko..maybe for a few days.

Well, now we look at each other and say, ‘That sounds awesome, let’s go check Bansko out!’ And if we like it (we do!) we stay until we’re not having fun anymore!

So that’s pretty much where we are going: anywhere!

Wait, that’s your ITINERARY!? That’s not aN ITINERARY!

Yep, pretty much! And sure it is! 

Well, another vague notion is ‘Chasing Spring.’

When we talked about what to call this blog, that was a top contender. We love Spring: warm but not hot. Rebirth, renewals. And even more importantly, SHOULDER SEASON!

We love going to popular places that are not in high season but also not in low season…shoulder season!

It’s all about affordable luxury travel. Shoulder season means going to popular and gorgeous places at a fraction of the cost because the crowds haven’t quite started showing up yet…or have just gone back to work at the end of the holiday season.

But that’s really just a couple of notions. Ultimately our plan is to have no plan.

To go where the fates and our collective gut guide us to what feels right…so long as there is fast internet so we can work on the business!

And here’s the really important thing about our plan of having no plan: we firmly believe that this lifestyle will continue to change us in ways we can’t even imagine right now.

Planning as we go leaves us open to growth, change and experiences beyond our current comprehension.

By being open to anything we will be open to everything…and maybe…just maybe…everything will happen anywhere we go.

And if we can get there in business class or upgraded economy then all the better!!!