From the Bay, From the Bay to the Blue Ridge

Learning To Sail, One New Sailor’s Story

Jonathan Newton began sailing about five years ago. Now he owns a sailboat is a board member at his sailing club.
Jonathan Newton began sailing about five years ago. Now he owns a sailboat is a board member at his sailing club.

Although it may sometimes feel as if everyone sailing on the Chesapeake Bay and its tributaries got started as children, plenty of gung-ho and competent sailors didn’t take up the sport until adulthood. Jonathan Newton is one such sailor. Newton, who owns a Laser sailboat and is a finance and accounting professional living in Annapolis, began sailing at age 27, and now, just five years later, he is racing and cruising big and small boats and is the member-at-large representing one-design sailors on the board of West River Sailing Club (WRSC) in Galesville, MD. We asked Newton to share some words of advice to folks who wonder how to get started in sailing.

How did you start sailing? I was invited to a Wednesday night race in Galesville. I sat in the companionway of a Tartan 27 in my socks and tennis shoes. I totally left sole marks on the deck. (Editor’s note: Inexpensive shoes that won’t leave scuff marks are best; leave the blacks-soled shoes at home.)


What kind of boats did you sail at first? I began sailing small boats because I found it was the quickest way to earn time on the water. I think it’s helpful to learn in a small boat because the boats are so responsive — or perhaps at times I am so sluggish!

Did you take sailing classes? I took several classes at WRSC. As I began crewing on big boats, my experience sailing small boats seemed to be welcomed. In addition to sailing classes, I already had my boater license and have now started working towards my Club Race Officer designation.

What keeps you coming back out on the water? Recently a gentleman, who was probably born in a boat, said to me that he’s always enjoyed the idea that as a boat passes through the water, it seemingly heals itself, as if it never happened. I find the notion that the energy around sailing is temporarily yours to be a very fitting sentiment. And then it’s ready for the next sailor to enjoy and interpret.


What obstacles, if any, did you encounter? After I got a handle on the vocabulary and a couple of knots, I looked for skippers and crew with strong communication skills and a willingness to mentor. There are a lot of boats in our area looking for crew, but it may take a couple of boats until you find a good match.

Financially, while every hobby has its associated costs, I’ve found getting involved with sailing can be reasonable. Most skippers have extra gear and are happy to share with their crew. I made it through my first season (spring to early fall) with very little money in. I purchased a couple of tech shirts, water shoes, and gloves, and I already had a light rain jacket.

Where do you sail now and how often? I’ve had fantastic opportunities to sail historic waterways and beautiful harbors and to meet people and hear great stories, but I most enjoy cruising and racing where the water meets the shore naturally. I try to sail as often as possible. I race and cruise on large and small boats. Among my favorite memories is cruising with friends on a weekday evening during the summer.


What’s your advice for those who want to start sailing? Joining newsletter mailing lists and checking out sailing club websites kept me up to date on local events and activities. There are many sailing organizations in the watershed listed on U.S. Sailing’s website (and I’ve used the list to contact fleet captains of specific classes and organizations that I wanted to learn more about.

I’ve found that YouTube is a great repository for learning and enhancing my sailing skills. From the basics of boat handling tips to advanced tactics, it’s all there.

To meet people in the sailing community and look for crew opportunities, local resources such as SpinSheet Magazine’s crew listing service at and spring party are invaluable. At times I was bold; I did some research on the boats on the list and then sent a note or cold called the captains with a little bit about myself, experience, and season goals. For those who responded, it was that first step to getting out on a shakedown sail.

Written by: Beth Crabtree
Beth Crabtree, associate editor at SpinSheet Magazine, works closely with columnist Molly Winans and writes articles that inspire people to try sailing. Readers who are interested may visit

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