Jeannie Martin had always been adventurous and curious, so when her friends Captains Kristin and Doug Sharpe took their high-school-age kids on a one-year cruise from Annapolis to New England and down to the Caribbean and back, it opened a door to a new world that captivated her imagination. Never having been exposed to sailing, she was fascinated by the idea of exploring the world this way and wondered, “How does one do that?” Here Martin shares how she got started on her own sailing adventure.
Captivated by a friend’s cruising adventure
I started by meeting Kristin for lunch. She told me about various sailing schools, and I found The Sailing Academy in Deale, MD. There I took American Sailing’s Basic Keelboat course (ASA 101) in 2019 on an O’Day 29. Learning the terminology felt like learning a foreign language. The physics were fascinating and mixed my romanticized impressions of sailing with the practical skills, science, and engineering.
The pandemic interrupted my sailing pursuits, but in 2023, I took ASA 103, Basic Coastal Cruising, at the Maryland School of Sailing and Seamanship in Rock Hall. My instructor, Yvonne Brandt, was wonderful and truly inspiring; she was the first female captain I’d sailed with, and she has been my mentor ever since. Being in a class with two other women who noted I seemed like a “natural” gave me my first real boost of confidence.
Finding a sailing community
Yvonne recommended SailTime Annapolis, and I joined immediately. Along with access to ASA instructors, SailTiime provided an environment in which to learn, ask questions, and become part of a welcoming sailing community. In January of 2025 I took ASA 105, Coastal Navigation, taught by another fantastic instructor, Captain Rick Robey.
With SailTime I had the ability to try different boats, and I could focus on sailing without the burden of boat maintenance (Silas Denton takes amazing care of the SailTime Annapolis fleet and is on speed dial for anything members might need).
At that time, I was commuting 90 minutes to the boat in Eastport from Leesburg, VA, so for me another benefit was using SailTime’s boats as a place to stay. I’ll never forget the “badass” feeling of my first night sleeping alone on the boat in the marina.
My husband and adult children have earned certifications through SailTime, and they crew on the 2019 Beneteau Oceanis 35 Carbon that we have been sailing. This year Carbon will be retired from SailTime’s fleet, and we will move to Little Bird.
Taking a Big Leap
In March of 2025, I took a big leap and completed a week-long advanced course with LTD Sailing in Grenada (LTD stands for Living The Dream) where Yvonne teaches in the winters. There I earned my ASA 104 Bareboat Cruising and ASA 106 Advanced Coastal Cruising certifications, which included a 24-hour sail with night watches and manual navigation. That experience truly made me feel like a competent sailor.
Just last month (February 2026), I participated in an LTD sailing flotilla in the Sea of Cortez on a Lagoon 45 catamaran. I was joined by two girlfriends who are experienced with powerboats but were new to sailing. During this trip I earned my ASA 111 Sailing Review certification and continued to firm up my skills.
Did you encounter any obstacles? How did you overcome them?
I certainly had a romanticized impression of sailing and didn’t initially realize how technical and challenging it is. However, that challenge is now part of the enjoyment because there is so much to know, making it a lifelong pursuit in that it is intellectual, sporty, and an opportunity for leisure, community, and socializing.
My main obstacle was self-doubt. Because I started in my mid-50s, I worried I was too far behind those who grew up on the water and around boats. I was also concerned about how a middle-aged woman from the suburbs would be received in a sport with such a “rich and storied” heritage. I’ve since learned that true sailors love to share their passion and teach others. I am so grateful to those who helped me, and I hope to pay that forward.
As mentioned, I had a 90-minute commute to Annapolis, where sailing had been drawing me. Life circumstances finally cooperated, and this year we moved into our new house, which is only 10 minutes from Eastport and the boat! We hope to join one of the yacht clubs here, and I hope to get involved in racing and volunteering with the youth sailing program. I am also signing up to be a crew member and skipper with Chesapeake Region Accessible Boating (CRAB) this season.
What would you tell someone interested in learning to sail?
Try it! There are so many entry points, whether through friends, charters, or the ASA series of courses, which are excellent steppingstones that will connect you with instructors and the wider sailing community.
