Jolly Hobos Travel First Anniversary

Updated: Sep 3

To be honest, when we headed to the Brisbane Airport on September 1st 2019 for a one-month stay in Hokkaido, we didn't have the "jolly hobo" lifestyle/journey in mind. All we wanted to achieve was a test of the concept of being digital nomads by spending a month in Japan before we went to base ourselves in North America for the foreseeable future due to Brad's work.


We had talked about wanting to slow travel for years, but didn't think the timing was right back then as there was always something else that needed to be worked around. So that day one year ago when we headed to the airport we weren't 100% prepared for full time travel, especially when it came to belongings. We had a couple of suitcases already in Colorado and packed up the rest of our belongings that we hadn't already sold or given away to take with us. Needless to say then, our luggage was not really optimised for the full time traveller, and we hadn't even considered starting our travel diary "thejollyhobos" blog either.


The Hokkaido experience certainly gave us that taste of freedom living like a digital nomad does. That was the first time in our lives that we had no home base. It felt a bit weird being a "hobo", but the benefit of exploring a place slowly while living like a local was very attractive.


After Hokkaido, we settled in Calgary Canada as planned for two months to be in the right timezone for working while waiting for the timing to be right to maximise our US stay. During that time Brad's work situation changed, giving us some extra flexibility. Subsequently we decided to make an adventurous move by basing ourselves in Mexico for a while rather than heading over to Colorado as previously planned. We would stay put for three months to maintain the stability for work's purpose. That counted as our first pivot during this one year journey.


The three months in San Miguel de Allande was fantastic and really worked as a "soft landing" for our "jolly hobo" journey. We realised that we no longer needed to wait for the perfect timing - we were already on the journey of slow travel! With much excitement, we planned out the whole year's travel, booked all the flights and accommodation to demonstrate our commitment. That turned out to be a newbie's mistake - especially for the year of 2020 out of all years!


By end of February 2020 when our time in Mexico came to an end we had landed in Seville Spain as news channels around the world were already dominated by COVID-19. Two weeks into our stay the big lockdown in Spain began and we had to make our second pivot quickly - fleeing Spain and seeking out a little safe haven in the UK. Like many other travellers, we had to abandon all travel plans due to border closure and flight cancellations for at least three months, and so it was that we spent those three months in safety and isolation of the UK.


By mid June, we managed to get onto the first flight out of London to Split Croatia. It's here that we re-gained our sense of freedom, enjoying a beautiful summer in a safe environment. Considering what has been happening in the world this year, we are very grateful to call Croatia our temporary home for three months as we explored Split, Hvar and Zagreb.


During all that time in the UK and then into the summer months in Croatia, we continued to cancel booked flights and accommodation on a rolling basis for the rest of the year due to ongoing border closures, flight cancellations and the ever changing rules of border crossings as countries battle COVID-19. We have patiently spent hundreds of hours on hold with credit card companies and airlines trying to get refunds and credits for all the bookings we had, as well as monitoring Airbnb and other booking sites like a hawk for changes to their cancellation policies and covered dates for free cancellations.


With our three month visa in Croatia coming to the end and border crossing and flight schedules still being very volatile, we spent countless hours exploring options for the next stop, and have settled on one final realistic destination - Portugal. Although at this very minute things are looking positive for travelling to Portugal, we are fully prepared to adapt to whatever changes that may come up at the very last minute.


If this one year journey taught us anything, it would be flexibility - being flexible with travel planning, daily schedules, living environment and mindset! The other lesson we have taken is don't book everything too far in advance because you never know what will happen.


In conclusion, our first year of slow travel was something like this - stumbled into the"hobo" journey, planned with a little too much enthusiasm, pivoted twice and had a long pause. Who knows what the second year will look like, but it's all part of fun, isn't it?!


Year One Jolly Hobo Journey Tally

Counties Visited: 7

Longest Stay: a tie between San Miguelle de Allende, Mexico and Crowthorne, UK

Flights: 15