Like many people, my wife and I used to dream about quitting the daily grind and leaving Canadian winters behind for a different life in a warmer climate, and now, for better or worse, we are actually doing it.

This year, we’re putting the finishing touches on major renovations to a historic villa in Abruzzo, Italy and in May 2016, our boutique tour company will host its first official guests.

It sounds romantic, and in many ways it is, but our journey from comfortable careers in Ottawa to major investments and uncertain future in a foreign country has been full of twists and turns, big decisions, good luck and bad and healthy doses of humour and humility.

Over the coming months, I’m going to lay out more detail of how we got to this point, but I can tell you now that it started with a love of travel.

Soon after my wife Lisa Grassi-Blais and I met in 2000, we started travelling the Caribbean and Central America independently. We usually rented cars and followed our noses over back roads to out of the way remote places. In total, we spent several months in the Dominican Republic, Martinique, Honduras, Nicaragua, Costa Rica and Saint Maartin getting lost, having adventures and very rarely staying in a pre-booked hotel. We even planned out our 2002 wedding day while bobbing up and down in the waters of a remote Dominican beach near the border with Haiti.

Each time we’d return from a vacation, I would start thinking about opening some kind of tourism business – usually a hotel and tour company – in the area that we’d just returned from. I’d search the houses for sale websites, look for businesses for sale, calculate how much equity we had in our house, and rough out other plans.

I spent so much time on the internet at work, I half expected my bosses to take me aside and tell me to knock it off. I always liked my jobs, but I would have left on a wing and a prayer at pretty much any time because I’m just that kind of guy. Lisa is smarter than me, so aside from being an effective way to distract myself from work, it really was just day dreaming.

Then things changed.

In April 2006, Lisa and I, her mother and other family members took a trip to Italy, including a trip to Abruzzo where Lisa’s grandfather was born. It’s a diverse and beautiful region east of Rome filled with hidden treasures and undiscovered landscapes.

Nobody in Lisa’s family had ever been to Italy, and they had lost contact with relatives in Italy decades ago. Some incredible things happened on that trip.

We found Lisa’s family’s beautiful ancestral village high in the Apennine Mountains in the southern L’Aquila area of Abruzzo. Lisa’s mother met first cousins in their 80s and 90s she had no idea existed. A second cousin drove 300 kilometres one morning in a desperate attempt to meet us, explain the family’s history, and to urge us to return for the annual homecoming festival in August when hundreds of family and friends return.

That trip was the start of a series of events, changes and decisions that have led us to where we are today.

There’s risk in everything, especially in big, life-changing decisions. We looked long and hard at the pros and cons of doing this and, importantly, not doing this.

At the end of the day for us, the bigger risk was to not move to Italy and then have to live with the knowledge that we could have tried to do something thousands of other people like us dream about doing but didn’t do it because we chose to play it safe.

That was just too big of a risk.

Next Blog: Who is Lisa Grassi-Blais?