A chance sailing trip with a friend from work led me to wonder if I could learn to sail. After all, I’m a woman, and the sailing world seems to favor men. I am not athletic; I didn’t grow up in a family where we learned about boating; I would be starting late, since I was in my thirties; and I suffer from seasickness. What I discovered over the next twenty-five years is that I could indeed learn to be a competent sailor. But I didn’t expect to be an expert overnight. Instead, as a novice, I layered on new knowledge slowly, over time, through experiential learning. This book describes the process whereby this happened. Using examples from trips along the coast of Maine, New Hampshire, and Massachusetts, it reviews the essential knowledge needed to be a sailor as well as explanations about the parts of a sailboat, major boat systems, and tasks associated with maintaining a sailboat. It also discusses some Zen-like attitudes that lead to successful and fun sailing, such as focusing, the no-blame rule, and stripping down to the essentials. Unlike some other sailing guides, this book points out that sailing can be a lifestyle that includes many dimensions. It’s not just about getting a boat to sail. Traveling by boat is a unique experience, and visiting small coastal New England communities is an adventure. Learning about history, art, ecology, star constellations, technology, and birds are only a few of the kinds of activities that can be built into a rich and rewarding sailing experience. This book will be helpful for people who would like to learn to sail but who are intimidated by the process, particularly women, fledgling sailors just starting out, and families with children.