ASA Featured Instructor: Amy E. Skillman

By: Instructors, Schools, women on the water

Captain Amy E. Skillman of Sailtime Annapolis Sailing Academy

Captain Amy Skillman grew up sailing and grew up with four brothers. The experience that she garnered sailing with her adventurous family has prepared her for a life of teaching. Understanding the roles that are played on a boat as well as how personalities develop from those roles has contributed to Captain Skillman’s approach to sailing. Captain Amy Skillman’s shared much about her sailing philosophy and it is intoxicating. It makes me want to sail the Chesapeake with her right now.

Captain Amy E. Skillman is ASA’s Featured Instructor

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ASA: What got you into sailing?

Captain Amy E. Skillman:

I grew up on a lake in Michigan. My parents told me I learned to swim before I could walk, so life in and on the water came naturally. I was blessed to grow up with very adventurous parents and four equally adventurous brothers. My father bought us a Super Porpoise sailboat when I was about 13 and that got us all started. I remember our big challenge was to flip it all the way over and back up the other side without getting wet. Before long, my brothers started racing with another family on Lake St. Claire and eventually in the Race to Mackinaw Island from Port Huron. My interests gave way to others until one of them bought an Ericson 46 and wanted his family as crew. I started sailing again and raced with my family on Lake Huron for five years. It didn’t take long to realize the only way I was going to move up from bilge rat to deck work was to get my own boat and sail it locally between my trips to Michigan. I was living in the Mid-Atlantic by then so I started sailing on the Chesapeake Bay. That was the late 1990s. I started teaching for BaySail School and Yacht Charters in Havre de Grace in 2005 and for Sailtime Annapolis in 2018.

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ASA: What was your most memorable student or class?
Captain Amy E. Skillman:

Oh, there are many, including several adventures teaching in the Caribbean. But my first thought in response to this question is my “Storm Team.” This was several years ago. It was the last day of a three-day 101 class in Havre de Grace at the top of the Chesapeake Bay. We had sailed about 3 nautical miles south to a set of islands for lunch. We were on the anchor, enjoying the beautiful clear sky to the south, when I heard thunder. The sky to the north was getting dark so we pulled up the anchor and headed up the channel to the base. About halfway back, a tug boat went past us with all its lights on and literally disappeared into the thick of the clouds ahead. I realized we weren’t going to make it to the base before the sky opened. So, we dropped sails, did a 180 in the channel and went back to the islands to wait it out. My four brand new students handled those sails, drove us back to the islands, and got the anchor set perfectly. We all jumped below decks just as the squall and rains hit. They were exhilarated by the experience and by their competence. I was so proud of them I wanted to pass them all right there (I didn’t. They still took the test; but they aced it)

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ASA: Your favorite place to sail?
Captain Amy E. Skillman:

With over 8,000 miles of shoreline, the Chesapeake Bay has so many nooks and crannies to explore. There is always something new. And after having sailed in the Caribbean for 10 years, I get a physiological yearning to return every March. But I have to say that sailing in the Sea of Cortez was magical. We never saw another boat. The winds were consistently brisk; the temperatures in mid-October were lovely, the sunsets never disappointed, and there were lots of islands to explore. We swam with sea lions and bought fresh fish from the local fisherman returning to this small island home. I have only sailed there once but would go back in a heartbeat if given the chance.

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ASA: What do people not know about sailing that they should?

Captain Amy E. Skillman:

The boat is NOT going to flip over. It is designed to stay upright unless of course, you take it out in weather you should be avoiding. Although we teach you how to be prepared for sudden mishaps, they are few and far between and usually become the stuff of the good stories we tell. The media is swamped with sailing disasters. They are instructive, but not typical. Circumnavigator, Pamela Wall once said 95% of the time, the weather is lovely. I think that is about having knowledge and making choices.

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ASA: Why do you Sail?

Captain Amy E. Skillman:

The moment I step on a boat, I can feel my shoulders relax. I sail for the peace and quiet and I sail for the way the wide open sky fills me up. I sail because it makes me feel humble, competent, and courageous all at once. I also sail for the stories.

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ASA: How do we attract more women to sailing?

Captain Amy E. Skillman:

Offer all-women sailing weekends, all-women sailing courses, and perhaps all-women sailing clubs. Give women the opportunity to learn outside the dynamic of their relationships with men. Give them role models through women captains, writings by women sailors, and places (like the great Women Who Sail FB group) to talk with each other about their fears and concerns. Studies show that women have increased performance anxiety around men – this is why all-girl high schools are so successful. It is amazing how easy it is to defer to the person who exhibits self-confidence. By deferring, we don’t learn. When I was racing with my brothers and learning the ropes of a larger boat, it was often easier for them to just do something themselves than to take the time to show me. I finally had to point out that I will never learn if I don’t do it myself. I also found that if I understood the why of something, it was easier to remember the how. That gave me knowledge which also gave me confidence. It was an important moment of awareness for us.

Every potential sailor (men and women) should watch the film Maiden about the first all-women sailing crew for the 1989 Whitbread race around-the-world. It is a beautiful study of how we second-guess ourselves and get caught up in other people’s notion of what success looks like. For the most part, women learn differently than men, we use our bodies differently, and we have a different relationship to nature and the elements. Making space for that kind of learning will attract more women to sailing.

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ASA: Are there obstacles to sailing for women that are not widely known?

Captain Amy E. Skillman:

It is probably widely known, but the biggest obstacle is fear; that, and men’s disregard for that fear. We have to sail to the most common denominator of those on the boat. The last thing I want to do is scare someone away from sailing. My adventurous brothers (whom I adore) are all racers and hot-doggers. They love nothing more than pushing the boat to its limits. For the most part, their wives won’t sail with them. Women (not all women) are interested in sailing for the peace and quiet. Men (not all men) are interested in testing their limits and conquering the elements. Finding a balance between the two will help to balance the boat.

As much as men do not believe they are yelling, women hear them as yelling. This makes them feel like they are failing as crew. Change up roles, especially those defined by your relationship. There is nothing more satisfying than successfully docking a boat. Let your wife learn and savor that feeling. A better understanding of how a boat works, and sailing that is peaceful, will engage more women.

It would also be great to develop focused ways to help women incorporate their children into sailing. Women tend to put their children first. Finding ways to bring them along, and incorporate them into the sailing experience will give women models for sailing as a family experience, not a race to the finish.

” I sail because it makes me feel humble, competent, and courageous all at once.
” – Captain Skillman

Captain Amy E. Skillman can be found sailing at SailTime Annapolis Sailing Academy and BaySail in havre de Grace.


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