We’re going sailing!

Brian and I have talked about and dreamed about going cruising for longer than I can remember. Brian, as a lifelong sailor, has always wanted to do this. I don’t remember when it went from something he wanted to do to something that we wanted to do. But it certainly was by 2008, which was when I seriously proposed selling everything, buying a boat and seeing where a life of cruising would take us.

He, very wisely, turned me down in favor of continuing to work, build savings and a land life. By late 2009, we had pivoted. Left a city we loved (Chicago) for a job opportunity in Toronto, Canada, a city in a country I had never even visited before.

We’ve spent the last 12 years building a home, a family and a life here. We bought and then renovated a house, the first property we’ve ever owned. We bought boats, first for racing, then for cruising. We had our two little boys, Oliver and Elliott. We’ve made fantastic friends, both in our neighborhood and in the sailing community. We’ve spent the last six summers cruising Lake Ontario with our kids and dreaming of the day where we might still cut loose and take off.

Turns out, that day was March 16, 2021. Brian concluded his 18-year-career in finance and this time, when he turned to me and I said, “Let’s go sail,” he said “Yes.” So, here we go! We’ve rented the house, the boat goes in the water in two weeks and when the kids are done with school at the end of June, we’re moving aboard and heading south.