I’ve been sailing for most of my life, starting out on an old, beat up sunfish that my brother and I would sail off the beach at my grandparents’ house and moving to progressively larger and more complex boats. I still take great joy in sailing small boats and have spent the last several winters frostbiting Lasers on Long Island Sound. Even so, every year as the crisp autumn days set in I feel an urge to point our bow south and explore new waters.
The first time I remember wanting to cruise was to help my grandfather sail his wooden boat from Chicago to the home he retired to on Cape Cod via the St. Lawrence seaway. That trip never happened, but the desire to experience new places under sail didn’t fade.
Eventually Melissa began sailing with me, first on protected coves in an old O’Day 23 we restored together, then on our Catalina 36 mk II. Over time our trips became more and more ambitious until we finally agreed that it was time to stop talking about cruising and do it.
Our decision was born out of having the freedom of fully remote jobs, the loss of a sailing friend, and the memory of my grandfather, who never took the sailing trip he dreamed of. I spent much of the summer preparing our boat, ensuring that we have reliable power and internet aboard to support our work. With the systems installed and stress tested we were out of excuses and it was time to take our leap.
