Cruising World


The key to getting your toes wet and learning how to sail is to spend some time on task. Any sea gypsy can tell you it’s easy to learn how to sail when sitting on the deck of a sailboat—and almost impossible to do ashore. Sure, how-to books and videos are great, but nothing compares to hands-on experience.

So the first goal is: Somehow find a way to go to sea.

A few years back, I bumped into a very handsome woman, a former CNN presenter, who met the dot-com entrepreneur of her dreams one fine day. He invited her out for a sail aboard his yacht the following weekend. Smitten, she flew off and took a quick basic sailing course in a concerted attempt to broad reach into his heart. One of the first things her boyfriend-to-be said to her the following weekend was, “I thought you didn’t know how to sail?”

“I didn’t—then…” she said, and explained.

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