Has there ever been a place where I felt more belonging… excitement… intimidation… yet an overwhelming sense of “I can do this”? Two patient, perceptive instructors and seven fellow students equaled an incredible introduction to sailing. Concise instructions gave structure to the ambiguous “sailing theory.” Beginning the day with the whiteboard classroom instruction, moving to sitting in the boat (the Topper) on the dock, then tethered to a rope in the “bathtub”, finally sailing around buoys in the harbor, and ultimately the surprise of sailing out into the open water past the runway to roll on the swells as the boat responded to my hold of the mainsheet and tiller, sails filling with the steady wind. She was my horse and we were in the open range of the seas.

“Sail different waters” … “It’s supposed to be fun” … “There’s only so much learning in the classroom will get you. At some point you have to go out there and learn how to feel the boat.” “Smooth like buttah.”
Words from sailing instructors when I began sailing. I began sailing in September of 2023. I remember the morning well. I was nervous but so very excited. I arrived thirty minutes early, quite unintentionally. So I ended up sitting on a picnic table watching the gorgeous turquoise ocean roll and splash, enjoying the peace and quiet of no kids. This was a step toward regaining my sanity after seven years of homeschooling and several military moves. Just the morning before, I had been selected from a lottery process to participate as a student in a group of volunteer-led sailing classes called the Wet Hens. That wasn’t going to begin until the following Tuesday. My MWR sailing classes were Wednesday and Friday, so next week and for the following month, I would get to sail three times a week!
My gaze drifted upward, to say thank You to God and ask for courage to do something new, and I saw something I had never seen before. A circle rainbow. A huge rainbow circle around the sun. What a sense of peace rolled over me when I saw that. It was going to be an exciting day!

And it was. When 9:30 rolled around, I met my two sailing instructors, one of which I knew from my husband’s work, and my fellow sailing classmates. The one other beginner and I headed to the classroom to receive basic sailing theory instruction while the intermediates gathered their sail gear and chatted jovially. From the beginning, as the sailing instructor welcomed us to the class, I knew this was going to be more than just a class about sailing. Within the classroom, tears began to well up in my eyes. I was crying over sailing theory… it was something new and intellectual, a new mental challenge my mind had been craving. Something I could learn about in a classroom but then immediately go out afterward and put to practical application. Tangible rewards and feedback. I was in the right place! Where had sailing been all my life?!
From the classroom we moved onto the docks where we practiced twenty or so tacks just sitting in the Topper on the dock, holding the mainsheet and moving from side to side, our instructor simulating the movement of the boom over our heads. As my fellow classmate practiced in the grounded boat, I went through the motions on the land, repeating the instructor’s words in my head: “Push the tiller away. Boom crosses over. Center the tiller. Reach for the other side. Take your time exchanging hands with the mainsheet and the tiller.” We also practiced capsizing and righting the boat. That was refreshing. So thankful for the gorgeous blue waters of Hawaii! Next was sailing on a tether within the “bathtub” area, protected by the dock and Foster Point. I felt so clumsy and unable to control the boat. It was, honestly, quite frustrating but great at the same time. I had not expected to be a rockstar right off the bat anyway. My body just needed to get used to what it needed to do.
We ended the day by returning to the classroom for a summary of what we learned and a debrief of what we experienced. Both my classmate and I laughed at our first attempt at sailing, but our supportive instructor encouraged us that it was just the beginning. More time in the boat would help. “There’s only so much learning in the classroom will get you. At some point you have to go out there and learn how to feel the boat.” So I drove home, thrilled to be on my way to learning how to sail and chomping at the bit for the next sailing lesson!
After I had been sailing for three months, three days a week for the first month, one day a week the second month, and two days a week the third month, I hit a bit of a wall mentally and emotionally. Here is what I wrote:
“Sailing is life” continues… at the beginning, as things clicked, I really felt like I was starting to know what I was doing. Now, even though I have a little more sailing under my belt and have been introduced to more pieces of the sailing puzzle (i.e. racing kit for the Laser), I somehow feel I know less. I have entered a zone of doubting myself and making mistakes and feeling frustrated. Gone is the free sensation of accomplishing the basic principles and not capsizing a boat. How do I return to that open, exhilarating experience? Where do I turn to rediscover the freedom and confidence? Is this the land of the “intermediate” or perhaps I’m more of an advanced beginner? I need new skills to navigate this terrain.
Life is like that too, isn’t it? Starting a new job/relationship/move can feel exciting and refreshing at the beginning, but everything slows down at some point and becomes a bit more tedious, frustrating, humdrum in a way, if only because it loses the newness part of the experience. When it becomes tempting to want to walk away, or to not care as much, that is when we are supposed to stick with it, isn’t it? That’s when things really have a potential to affect us and change us. Dive in, give more, learn from those tiresome mistakes, seek further assistance to strengthen understanding, embrace the fact that there is so much more to learn and never stop asking questions to improve.
I continued to take lessons twice a week and sail at every other opportunity provided, often averaging three sails a week. My time in Hawaii drew to a close, and I am happy to say that by the end of it, I had sailed over one hundred days on the water.
—— I wrote this over a year ago, this story of how sailing entered my life. I give credit to other instructors, women and men, who have taught me so much in a very short time, but it is to these two instructors that I owe my true understanding of sailing. I’m sure I will share more lessons I learned from these incredibly patient, kind, fun people. My heart overflows with gratitude for people who spend the time and energy to teach something they love to others. I continue to love sailing and will for the rest of my life. It’s in my soul now. —–
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