“Where are y’all headed?” Cruisers ask each other this question reflexively. The query leads to great dock discussions and exchanges of information. When I had a dog with me, the

pronoun of choice in answering was “we,” as in “we’re headed north or south, or we have no idea.” My dog usually agreed with whatever I said. Once dogless, I was stumped on how to answer. As a female boat owner and occasional single handler, there is no “we.” An informal poll reveals most men cruising solo don’t get this question.

So, the choice is to move along with a destination-focused answer to a polite question. Or state one’s solo status, which is often met with more interest than the itinerary inquiry. This is the story of how to even be on the water to be asked this question. A great trip to Charleston, SC, provides some answers.

I cruised from Virginia to Florida in 2016 on my 42 ft. Grand Banks Motoryacht, Waterlily. This was accomplished with strategy #1 for how to cruise as a singleton: identify a knowledgeable, decent person who is invested in supporting other boaters and is going in the same direction. Offer to pay the person even if they refuse. This isn’t buddy boating. It’s a teaching-learning relationship, which, fortunately in this case, morphed into a lasting friendship with Tom Hale, boat builder, educator, and engineer...

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