By Kevin

A confession is in order. We are not cruising gurus.

Although we’ve owned a 32′ sailboat on Lake Michigan for the past 7 years, both Jen and I were in our thirties before we took up sailing as a pastime. Somewhat embarrassingly, though we’ve taken several sailing courses over the years, we’ve only really used our lake sailboat for daysails and weekends tied to a dock. (Well, ok, there were a few short overnight trips to Wisconsin and across the lake.)  

Other than that, our experience is limited to two preparatory events. We did a family charter on a 34′ Beneteau via the Moorings back in 2007. It was an amazing week in the BVI’s that really helped me get a juicy taste of just what the Caribbean islands have to offer when you are traveling by boat.

Later, in 2010, I crewed aboard a 46′ Bavaria for an Antigua to The Azores yacht delivery. That allowed me to experience 19 straight days at sea. During that trip we had day after day of rough seas, pounding into wind and steep waves, and day after day of beautiful downwind sailing with only dolphins as our fellow travellers.

But, daysailing, week-long charters and cross-Atlantic deliveries are not cruising. Cruising is self-sufficiency, logistics, weather windows, boat maintenance and, I hope, plenty of relaxing days hanging on an anchor. At least this is what I imagine cruising will be, as I sit in my comfortable home office in suburban Chicago, three weeks away from moving aboard Real Life in Ft. Lauderdale.