ASA Featured Instructor: Hilary Howes

By: Instructors, Schools, women on the water

Captain Hillary Howes found the magic of sailing in the San Francisco Bay and her life has taken her across the country to the Chesapeake where she teaches for Annapolis Sailing School. As her professional career wound down she turned to sailing and boats and now her next chapter involves sharing her love for the wind in her sails with new students.

Hilary Howes of Annapolis Sailing is this month’s Featured Instructor.

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ASA: What got you into sailing?

Captain Hillary Howes:

I grew up in San Jose, California, near San Francisco Bay, and loved the idea of sailing. I went to college at San Francisco State University, and one semester’s PE requirement was full-filled by a once-a-week 4-hour class on Small Boat Sailing. I loved it and got to sail on and outside San Francisco Bay on friends’ boats over the next few years. However, my busy life, career, and parenting meant those opportunities didn’t come up too often. I moved to the Chesapeake in 2000, and by 2016 I bought my first boat. Covid released me from my busy career to increase my sailing as I shifted into a retirement that included being a yacht broker and sailing instructor.

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ASA: What was your most memorable student or class?
Captain Hillary Howes:

We have classes of 3 students to one teacher on Rainbow 24 keelboats that we sail right off the dock. I was warned that one of my students was the wife of the school owners oldest friend. It wasn’t clear if she was a (not so) secret-shopper or if I got assigned her because they thought I would make a good impression. My other 2 students turned out to both be emergency room doctors that were married to each other. We had a blustery day their first day and they were all doing well. We were returning to the dock when the wind went from 12 knots to 31 knots in a matter of seconds just when my student was trying to enter the tiny opening to our docking bay. The sudden wind overpowered her and I was forced to take the tiller and do an emergency 180 tack that missed the dock by inches. That 180 in that wind brought us to a broach but everyone stayed in the boat. Dropping the main and sailing by jib alone got us into the dock while the wind continued to howl. The ER doctors kept their calm (of course) and were a great help in the emergency. I proved my metal in a tough situation that day and was commended by students and staff alike.

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ASA: Your favorite place to sail?
Captain Hillary Howes:

I love the Chesapeake Bay and San Francisco Bay, but I have had the opportunity to race and cruise in the BVI, bringing back the fondest memories. You sail through blue water to spectacular island destinations with mooring balls and resorts all over the place. Snorkeling, exploring, eating, and beach time in between short blue water sails! It’s pretty sweet. There is still so much for me to discover, though.

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

Captain Hillary Howes:

My impression is that people think that sailing is elitist, expensive, and hard to learn. All of that can be true, but you can participate in sailing at every income level, you don’t need to own a boat, and you can learn to sail in a weekend and then spend the rest of your life mastering it. With lessons, you make yourself a valuable member of a crew that, along with people skills, will get you invited onto others boats for racing or cruising. If you are handy, even an inexpensive boat can take you through a bay or across a lake to enjoy the interplay of wind, waves, and sails.

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ASA: Why do you Sail?

Captain Hillary Howes:

I love the water, and boating puts me in my happy place. I’m a recovering workaholic, and I think I sail because it’s more complicated than motoring. There is always something to tweak or adjust as you cruise along and everything to maintain a watch for so I never get bored aboard. There is incredible joy as the sails fill and the engine goes off. Knowing that I am moving along by harnessing the power of the elements of wind and water with my craft and skill is meaningful for me. Passage-making tends to be a spiritual journey, sometimes stressful and educational and other times reflective and beautiful. Meeting the wonderful people of this community continues to be an ongoing joy.

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ASA: Why Should People Sail?

Captain Hillary Howes:

People should sail if they love the water and want to participate in how they move through it. It’s a sport you can do while sitting down (for the most part). It’s a relatively sustainable pastime. The people who sail are just a wonderful group to know and hang out with.

Captain Hilary Howes can be found sailing the Chesapeake with Annapolis Sailing.


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