Search
  • Holly

How Sailing Began

How did plans change from being a working mom to wannabe sailing cruiser, with no previous sailing experience? It had to do with a man, but not in ways you might think.


In December 2008 I met him out in front of a local coffee shop for the first time. He was much taller than his picture looked and while his smile was nervous, bashful really, his eyes were captivatingly blue...Belize blue, and filled with childlike wonder. I had to check over my shoulder to be sure that gaze was truly intended for me, as I got suddenly nervous as I locked my car. We ordered our coffee drinks and found a table towards the back and stumbled to find the words to start a real conversation that originally began online just days before. I know, roll your eyes at me here. I had no expectation of meeting anyone decent on a dating website at that time so my bar was impossibly high. It was really unrealistic, and in hindsight was to protect myself from sociopaths and serial killers. I had divorced friends like me tell me terrible stories of online dating and I didn’t want any of it. Our conversation focused on our children, mine 12 and 10, his 8 and 6 at the time. He had this dreamy French accent, he talked about growing up in Brittany and how he ended up in the US living just one town over from me, and shared a lot about his children; he obviously adored them. He explained he once had wanted to sail his children around the world in a sailboat, but that it was unlikely now with his divorce. This idea was completely unimaginable to me, but the way he talked about his passion for open water sailing and being able to share that with his children, sounded both insane and inspiring.

Meeting a sailor

I grew up with little means and a lot of uncertainty, so it was really important to me to give my kids things I didn’t have. Live in a good neighborhood, in a decent house, near good schools, have a green lawn, a good job and a stable home life. That was the idea at least before my own divorce. My MO was about being a responsible adult, working hard, putting money in the 529 and walking a straight line into some unknown sunset. I wouldn’t say I was risk averse, I just lacked creativity and had an inordinate need for control at that time in my life – which is what happens when you are playing the game of 52 card pickup that comes with a marriage dissolution. You seek control in small places where you lack it everywhere else. What I also found refreshing was his European perspective on life, that we as westerners completely miss. At that time, I was ruled by my outlook calendar, my commute, my career goals and my children’s sports and school schedule. He talked about the importance of work/life balance, his love for traveling and living a simple life with his children. His kindness and ability to be completely in the present moment was alluring and completely unnerving all at once. His words were calm and soft, the conversation was easy and when I looked at the clock, three hours had passed. About six months later, I joined him on his small racing keelboat sailing on the Bay, out to a Delta, it was a Moore 24’, did I mention small? Turns out, it was the same boat he doublehanded during a transpacific race to Hawaii, a race he’s completed on this and other larger boats a number of times. It was during this trip he jumped up to put up the spinnaker and handed me the tiller. He told me to try to keep the boat flat and push the tiller the opposite way I wanted the boat to go – which makes no sense to someone who’s never sailed before. The little boat was surprisingly responsive and easy to maneuver once you got a feel for it and I loved the water, spending some summers on the Lake with my grandparents on their beat up old water ski boat and other water adventures. This helped nurture a special soft spot in my soul for houseboats and fishing.


Learning to sail on a Moore 24

Later that summer my careless optimism for sailing came to dead stop after two things happened. First, we sail in a Bay where conditions can change in an instant; wind, current, tide, fog. On one particular day the Bay had mixed emotions, one moment cheerful and sunny and the next, treachery and confusion. In an instant I appreciated that if I fell off the boat, he could come and get me, but if he fell off, we would both be pulled out to the ocean and both of us would die.


The second incident happened later that summer. We were taking down the mast after spending weekends that summer boat camping. We opted to tow it home since where we had ended up was too difficult to maneuver back without an engine. No, his boat didn’t have an engine…and the head was a black bucket with a seat…did I mention small?



Moore 24 - he sailed it to Hawaii doublehanded in the transpac race

We were in the air about 14 feet high on the boat trailer in a grass field that to our surprise became a parking lot when we walked back from lunch after having cleaned the boat all morning. He was straddling the cockpit with both hands in the air (he’s 6’2”) but the mast was towering high above. I was supposed to ease the rope (I mean the line) on the count of three, or was it after three? The line had its own mind made up and there was no easing from me, it went flying out of my hands and the mast snapped down to the side, where he teetered to one side to grab it before it fell over and hit the cars parked below.


Besides almost watching him fall over the side or get his brains bashed out by the mast, the mast broke at the base. We both stopped and took stock of the situation that could have really been bad, and we weren’t even in the water. I was devastated, I mean it was a new relationship and I broke his boat.


He sat me down and he said this to me...

"People who do stuff, break stuff."

Then he reassured me it could be fixed. By then, I was fully in fear realizing that his idea of fun wasn’t going to work for me unless I was able to climb up the learning curve quickly; from sailing tactics, to line handling, to reading maps (I mean charts). We sold his little boat and joined a sailing club, which doubled as a sailing school and charter operation. It came with all the classes and then you could charter their boats, which were bigger. I committed myself to taking the classes, which he took too, since it was something fun we could do together. I thought it was ridiculous because he had been sailing and racing for years, but he was fun to be around and I used to be cute back then and I was grateful he enjoyed spending time with me. Turns out this was great and helped me understand the concepts better and gave me practical examples that I could connect to. After a couple years, I had my sailing certifications done and we enjoyed day sailing in larger boats with fully functional heads. I’ll say, what a difference information has on your confidence and psyche. The lessons took the hocus pocus out of sailing for me and at least I could grok the basic principles, how to hail a mayday and safety, and man overboard procedures. While I’ve got a long way to go at this point, at least I know the boat physics enough to not freak out when the boat starts heeling over and enough practice to know what to do if someone gets ejected. There is comfort in that. Next we tackled Coastal Navigation, which I’ll be honest, wasn’t easy...for him yes, but not for me. I’m a liberal arts major and it turns out navigation is a peculiar combination of trigonometry, physics and algebra; I think I took those classes at some point in high school but never found any of it useful in everyday life. To my surprise I passed the navigation course which was a life highpoint for me, though...my kids were unimpressed. We began to plan for a bareboat catamaran trip in Belize through a local charter company; this is where the fun begins. We sent out an all points bulletin to our friend so see how many we could enlist to help us split the cost...well, I mean, join our adventure. We soon had a full boat and had the trip of a lifetime.


Belize shouldn’t be missed though the navigating to coral takes nerves of steel. We went back a couple years later with a different group, that included a friend of ours who has since been a stowaway on every trip we’ve done since then. She’s good at accounting so she keeps everyone honest when it comes to splitting all the costs. She’s a ton of fun and is also from Brazil so she doubles as the entertainment especially after she imbibes on a couple glasses of wine. We have done a number of other trips, bareboat chartering larger and larger catamarans each time. This is what not to do if you want to hold onto your wallet, catamaran’s lure you in by spoiling you with great light, stable sailing and I mean...there’s just so much space!


Our little sailing hobby began to turn into a retirement plan as we talked about what it would be like to sail around the world after we retired - which was easily another 15 years out. We stuck a pin in that idea and moved on to the issues of the day, jobs, homework, swim meets, soccer practice and what to eat for dinner.


One day everything changed. I won’t go into the details of what happened, because it’s not my story to tell, but it’s important to understand how one day changed our lives. One of our children was struck by a car while riding a bike. The accident should not have been survivable, by everyone’s accounts including the first responders and all the medical staff. In the end a miracle happened and there was a full physical recovery. That’s about two years of crisis packed into three sentences. Like I said, it’s not my story to tell.


All of us were faced with what we all intrinsically know about how precious life is; our household, our blended family, our extended family and our community. Nothing prepares you for something like that.


Once the situation stabilized, my husband and I had a couple serious conversations about our priorities, what we wanted for our children and what we wanted for ourselves after our children moved on with their lives. We both had a whole new perspective on what was important and that time was never a guarantee. Suddenly our careers, our routines, our belongings just didn’t seem all that important in the grand scheme of things and we started to discuss what we really wanted to accomplish and experience in this short life we have. This is where people our age start to contemplate shifting their life purpose, perhaps teaching or philanthropy, running for office, or saving the planet.


We chose sailing. We chose it because we want to connect with new people and places, we want to see the world outside of hotels, airports and conference rooms in foreign countries (which both of us had experienced a lot in our careers). If I’m going to be born and die on this planet, I want to understand as much as I can about what it’s like for different people to live on it.


So we circled a date in the proverbial calendar and that was the day our priorities made a polar shift that changed everything. This was our way to move forward, circle a date.


We decided to call it a sabbatical because that’s all we could wrap our head around at that time. We didn’t know how, but we knew when, and if there’s one thing I knew I could count on to keep us honest it was a deadline - which is one thing my entire life I’ve never missed.


And so it was that our idea turned into a plan.




Related Posts

See All

We welcome your comments at the bottom of the page.