Clearly, she should be sailing.
An adventurous newly outdoorsy adult, Emilly S. Bartlett has hiked Patagonia and jumped in to sailing in a big way, so you might be surprised to learn that she grew up in rural Kentucky spending most of her time indoors.
In 2025, approaching her 50th birthday and winding down her work as a self-employed management business consultant, Emily relocated from Nashville, TN, to Glen Burnie, MD, and moved into her grandparents’ home, which she had visited regularly since childhood and purchased before the pandemic. One day, while sitting on a beach looking out at the Bay, Emily Bartlett saw a sailboat underway. “Something clicked,” she says, “and almost instantly, it became so clear to me that I should learn to sail." Here she shares more in her own words.
Off to a good start.
“I signed up for American Sailing’s Basic Keelboat courses, ASA 101 and 102 at Annapolis Sailing School and found that the wind, sun, and water are an incredible way to be immersed in nature, so I went on to complete ASA 103. I was thoroughly enjoying myself and wanted to try sailing internationally, so I enrolled at Aegean Sailing School in Greece, where I completed the Royal Yachting Association (RYA) five-day Competent Crew course.”
From the classroom to real-world sailing.
“With these courses under my belt, I signed up to be crew on a boat delivery from Annapolis to St. Augustine, FL. We started the journey with a 24-hour sail to Norfolk, VA, and I learned that I love night watches and going through large shipping channels. I learned a lot from the captain, but there were also some safety challenges. Our headsail blew out on the second night underway, and we were forced to dock in Wilmington, NC. I feel like that trip was worth 10 ASA/RYA classes. And next time I will be better equipped to ask better questions upfront.”
Embracing the struggle.
“With my new list of questions, I did a lot of research and found Rubicon 3, a sailing expedition company based in the UK with an emphasis on safety. I signed up for 10 days with 11 people aboard a 60-foot yacht in the Caribbean. We sailed from Antigua to Guadeloupe, Martinique, Dominica, and to St. Lucia. That trip is designed for travelers not tourists, with anchorages in more obscure locations.
With my background in business administration, I especially appreciated the program’s clarity around crew dynamics. “Both our captain and first mate were fantastic. We received incredible hands-on learning. No one jumped in to try and ‘save the day.’ Failure is a part of learning, and we were permitted to try and fail in a controlled environment. It turns out that one does not, in fact, want to miss out on the struggle.”
Race training
In February I joined North U’s performance race week in St. Thomas, USVI, for five days of instruction on boat handling, boat speed, and racing strategy, tactics, rules, and starts. I was placed in a beginner boat with four people and a coach. Annapolis sailors Kristen Berry and Margaret Podlich, two of my coaches, were excellent and helped take my sailing to the next level.
“As a consultant I have experienced many workshops aimed at creating high-performance teams, so I especially enjoyed the North U focus on team dynamics. For example, professionally, I know that high functioning teams use language that does not deviate. So, for me, having not grown up around boats, it was especially helpful to pick up sailors’ slang and colloquialisms, terms that I wouldn’t have learned reading a how-to-sail book. Understanding all the terminology will make me a better crewmember and teammate on any boat.
A summer focused on sailing
This summer I am working as the assistant director at Annapolis Sailing School’s KidShip program. I love the idea of helping kids learn to sail and feel comfortable around the water. Although I learned to swim as a kid, I didn’t learn the proper strokes until I took swimming lessons as an adult.
Looking ahead, I hope to earn my sailing instructor certification and teach sailing both in the US and internationally. I love working at Annapolis Sailing School and just passed the US Sailing Level 1 Small Boat Instructor course in June. As a prerequisite for that course, I took a safe powerboating class at SUNY Maritime College in Brooklyn, NY. I had fun and want to teach that class someday! Also, I’m racing on Toby Gandy’s Beneteau 10R Javelin on Wednesday nights, putting that North U Performance Race Week camp to good use!
What advice would you give someone considering learning to sail?
Do it! Today is the youngest you’re ever going to be. One word of caution is that if you perceive sailing to be luxurious, you should know it is actually more like camping on the sea. Be prepared to move between comfort and discomfort. While you are learning to sail, imagine what kind of sailor you might like to become: a cruiser, liveaboard, racer, ocean-crosser, instructor, singlehand? There are many types of sailing, and it is fun to try them all! I have discovered that I’ve actually been a sailor my whole life; I’ve just not been on the water. Sailors are my tribe, and I am thrilled to be on this path!
