To summarize us perfectly, it would be most appropriate to use our family’s Instagram page name – ‘The Winging It Family’. Ever since my husband and I met, we have always lived our lives by winging it and that has only continued to ring true once we brought our 3 young boys into this world. They are currently ages 4, 3 and 11 months and our lives have been anything but boring.

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We had the ‘what’, but not the ‘how’  

Before we found Boundless we were working 9-5 and spending the weekends filled with soccer games, birthday parties, and errands on top of errands! We knew we wanted to figure out how to slow travel with our kids long term but had no idea how we were going to make it work financially if we had no child care and had to spend our days planning the next location. We slowly began to make changes in our life to get us to the point where we could consider slow travel. We both got remote jobs and we started doing endless amounts of research on how other families travel with kids. Enter Boundless Life - which truly couldn’t have come at a better time. 

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Were we ready for island life?! 

We had originally signed up for our first cohort in Tuscany but changed to Greece at the last moment. We were a little concerned about spending 3 months on an island and wondering if we might go a bit crazy not being able to travel around much. Not to mention, we really had no idea what to expect having never travelled to Greece, let alone a Greek island in January! 

Boy, were we surprised from the second we stepped onto the island of Syros. We couldn’t have dreamed up the experience we had. From the people to the culture to the safety and more, we were blown away time and time again. We hardly ever left the island with what felt like a celebration going on every weekend including Easter, their carnival, Syros 5k and more. 

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A change of plans 

We had originally planned to stay just one cohort and then travel back to our home in America to figure out our next steps. Within just one week of living in Syros, we had already extended our stay for another cohort, keeping us in Syros for a total of 6 months (enabled by the Greek Digital Nomad Visa). A few factors that went into the decision to extend our stay were; seeing how safe our kids were and how they could just be kids, how friendly all the locals were towards us, and just the feeling we had from the moment we stepped foot on the island - like we were right where we were supposed to be. 

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Our highlights 💙

A few of our favorite memories while staying on the island included: parading down the street with all the Boundless families dressed like Trojans (including our 5-month old at the time) with what felt like the entire island to celebrate carnival; visiting a local olive farm watching the kids pick oranges and feed the chickens; the Boundless Life farewell ceremony at a local textile factory where we got a private tour and beautiful dinner and SO much more. 

What surprised me the most about our experience with Boundless Life were the lasting relationships that were formed with not only Boundless families but locals also. I never could have imagined how close we would get to people within a matter of months. It was truly magical! 

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New beginnings 

For any families thinking of doing Boundless Life in the future, I would say, don’t wait! It is life-changing!

Boundless life opened up our eyes to a totally new future we never imagined for our family. During our second cohort in Greece, we made the big decision to sell our house, put most of our belongings in storage and start to travel full-time. We came back to America for the summer to tie off all loose ends, regroup and officially become a digital nomad family! We are set to go to Tuscany with Boundless Life in September, spend December – April traveling solo, and then go back to our beloved Syros with Boundless in April where we cannot wait to see everyone again!