Mary Elkins, Modern Sailor and Now Full-Time Cruiser | Modern Sailing

Mary Elkins, Modern Sailor and Now Full-Time Cruiser

December 31, 2020

It feels a little strange to write an article for Modern Sailing in the first person, but when gathering ideas for the “2020 Modern Sailor Success Stories,” my team asked me to include myself. So here goes.

My sailing story begins in March of 2016 with stepping aboard and looking down the companionway of a Catalina 34 MkII named Pink Slip. I immediately thought to myself, "I could sail around the world in something like this." The sail that followed was mostly dull and windless, until the last 20 minutes when the wind suddenly gusted to 20 knots, followed by an accidental jibe and a near-broach. I was hooked. Before that day, I had never stepped foot aboard a sailboat.

A few sails later, I knew that I had to find a way to make sailing a bigger part of my life. Living in the Bay Area, I was only just getting by and couldn't imagine how I would manage to take classes and eventually buy and maintain a boat of my own. But I was determined to find a way. To follow my passion called for some creative problem-solving and taking some chances.

In March of 2017, I decided to quit my stressful job as an IT support technician to look for work in the sailing industry. When I saw Modern Sailing School & Club's ad for a Customer Service Representative on CraigsList, I knew the job was for me. My first day was May 1, 2017 and I have worked for MSC in many capacities ever since - as a Customer Service Representative, our CEO Leigh's executive assistant, the team’s IT support technician, a systems and process analyst, the office manager, and ultimately, my favorite role, the writer of MSC's weekly newsletter and website content. With each of my various duties and roles, I have never loved any job more than I have loved working with Modern Sailing – as I have never loved any endeavor more than I love sailing.

That September, I took the ASA 101/103 Basic Keelboat/Basic Coastal Cruising Combination Course with our COO, Captain Bill Moreland as my instructor. That course was the beginning of many character-building and life-changing sailing experiences to come. At first, I was terrified to make a mistake and timid about giving directions to the crew from the helm. With Bill's coaching and encouragement, I began to slowly gain confidence. A few weeks after earning my ASA 103 certification, I skippered my first sail with supportive coworkers as my crew. In the year and a half that followed, I logged over 100 days on the water by sailing after work and on weekends with my friends and mentors at Modern Sailing.

In early 2018, I had the opportunity to work as a first mate and chef on a private catamaran charter with one of MSC's captains in the British Virgin Islands. By the end of that charter, I had fallen in love with tropical sailing and it wasn’t so easy to be satisfied with simply sailing after work on San Francisco Bay anymore. I craved new horizons, blue water, tropical breezes, warm sunshine, and nights on anchor being rocked to sleep with the sound of water lapping on the hull around me.

In late August of 2018, sailing in messy but exhilarating conditions on the Pacific Ocean during my ASA 105/106 combination course, Captain Bill clutched my PFD as I committed my cookies to Neptune over the side. When I finished and slumped onto my seat under the dodger, Captain Stan Lander asked me, "So, Mary, are you rethinking this sailing thing now?" With no hesitation, I answered, "No!" There was truly nowhere else I'd rather be.

A week before the coastal course, I’d also bought my first boat – a derelict but salvageable Islander 28 – for only $910. I cleaned her up, made her my home, and learned that I truly loved the liveaboard lifestyle… until the seemingly endless days of cold winter rain arrived. I could no longer resist the call of blue water and warm sunshine and I became restless. It was time to get moving.

Modern Sailing School & Club is all about preparing others to make their sailing dreams come true, and as it turned out, I was not exempt from this philosophy. During the previous two and a half years, I had been a dedicated and hard-working employee. Thanks to Bill and Leigh’s support and encouragement, I had developed my skills and confidence as both a sailor and a writer. My role with MSC would evolve and continue as a remote employee when I moved to Florida in search of warmer sailing and a lower cost of living.

Shortly after I moved to Florida, I had the good fortune of meeting another sailor, Tim, who grew up in the Bay Area. Like me, he had cut his sailing teeth on San Francisco Bay. Also like me, he had a dream of buying a bluewater boat and cruising his way around the world. As our relationship grew, we frequently sailed his Hunter 30 on the turquoise waters of the Gulf Coast together and began to form a 2-year plan to buy a bigger boat, cut the dock lines, and sail away.

But then, COVID-19. In April, Tim was laid off from his job in the aviation industry. We talked it over and decided that the time to buy a bluewater boat was now or never. In July, we found a cutter-rigged 1993 Oyster 435 sloop for sale on the island of Carriacou in the Caribbean. After all the necessary surveys, we bought her sight-unseen and began to sell everything we owned. It seemed crazy to our friends and family, but to us, not doing it seemed just a bit more crazy.

At the time, Grenada’s borders were closed and we had no way to get to our new-to-us boat. I also sadly figured that the coming change would be the end of my time with Modern Sailing, but I was mistaken. To my surprise, Leigh and Bill were thrilled for me and agreed to continue my remote work arrangement.

On October 17, as our plane descended over sparkling blue Caribbean waters to land on Grenada, I shed a few tears of joy. I was so happy to be back in the Caribbean! After five days of quarantine and negative PCR test results, we donned our masks and boarded a small ferry for a wet and wild 3-hour ride to Carriacou. Five weeks of sweat, blood and tears later, our boat finally splashed into the clear waters of Tyrrel Bay and we began our life as full-time cruisers, feeling a bit like the anxious parents of a newborn baby. During our maiden sail south to Grenada three weeks later, I thought a lot about Bill, Stan, Leigh, and all my mentors, coworkers, and friends at Modern Sailing.

Most of the 10-hour journey was exquisitely perfect downwind sailing with a few minor squalls and becalmed pauses between them. We marveled at our boat’s lovely, seakindly motion. Once on open sea past the southwestern tip of Grenada, the swell got much bigger and our route east put our nose dead into the wind and waves. Not wanting to prolong the bashing by tacking our way east, we decided to furl the sails and motor the remaining two hours of the trip.

Tim had never encountered seas like this and I think he was a tad uneasy at first. Having some experience sailing Coho II on the Pacific Ocean in 12-foot swell, I shrugged and was nonplussed, if not happy to be on the helm. As I confidently steered us the rest of the way, I fondly remembered that day on the Pacific when Bill held onto my PFD as I leaned over the rail. Upon arrival at Clarke’s Court Bay, Tim and I were greeted by a rainbow blooming into a full arch across the sky. After we were certain the anchor had bit in securely, Tim stopped the motor and we stood in the cockpit, staring at each other with a bit of awe. We hugged and congratulated each other on a successful passage. Words can’t really describe this moment. Although we know we’re still newbies with our boat, these foreign waters, and the full-time cruising lifestyle, we felt like real cruisers finally. We had arrived… and yet the journey has only just begun.

In only four years, I have come a long way from being a stressed-out IT technician wistfully dreaming what seemed like an impossible dream of sailing around the world. For my experiences sailing on San Francisco Bay and the Pacific Ocean with the support and encouragement of my mentors and friends at Modern Sailing who helped make the dream a reality, I am grateful to the depths of my soul.

Our first look at the full length of our boat on launch day.

New cruising friends took this photo of our boat under sail shortly after we departed Tyrrel Bay at Carriacou.

The stunning rainbow that greeted our arrival in Clarke's Court Bay at the end of our maiden sail.


Do you have a sailing dream? Whether you dream of sailing around San Francisco Bay or sailing around the world, Modern Sailing School & Club can help you get prepared to go with confidence. Your journey can begin with an email or a phone call to our friendly office at (415) 331-8250.

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  • Mike, Santa Rosa, California

    All of the courses and my instructors (JT and Stan) were extremely professional and full of knowledge and experience. I found I was able to learn from their experiences beyond the scope of the courses, and look forward to future opportunities to do so. I would highly recommend Modern Sailing to anyone.

  • John Kratochvil, Oregon

    I would like to compliment Stan Lander for his coaching, counseling and teaching Heavy Weather Offshore Sailing. Stan was very accommodating to all of the student's interests and shared his many years of insight on handling the boat in heavy seas. I would certainly recommend Stan and this course to sheltered waters sailors. My confidence in handling a boat of this size was certainly enhanced by the experience.

  • John Clark

    Every aspect of Modern Sailing - training, syllabus, course materials, quality of the boats, quality of the instructors, and the very friendly and helpful staff - exceeded my expectations. Modern Sailing has a first class sailing program in an environment with challenging winds and currents. I look forward to coming back to charter a boat and certainly plan to continue my sailing training.

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