Sailing has always intrigued me: its historical significance and the perceived freedom of going wherever the wind takes you. It all sounds so romantic. When it was suggested that I learn how to sail, ...

The benefits of living so near water is that you can pick up sailing lessons from the crew of a one-time Olympian without going much farther than your front door in a growing array of options.

This is how Will Bradshaw, director of the Port Jefferson Yacht Club Sailing School, reassures parents who are starting a 6-year-old off in sailing class, in the smallest sailboats available: “I ...