HOW WE STARTED
Origin story of how Charlene and I decided to start our sailing adventure 12 years ago today
Jack
9/1/20252 min read
Most people decide to start sailing after a beautiful sunset cruise or a relaxing day on a lake. For us, it started with a news story about a shipwrecked family, a Coast Guard rescue, and a scuttled boat in the middle of the Pacific.
Almost exactly 12 years ago in April, probably after the ski season ended, I came across a Times article "Rescued at Sea, Family is Safe". It was about a family of 4 with 2 toddlers sailing to French Polynesia who ran into compounding medical and mechanical issues about a thousand miles off the coast of Mexico. They were rescued by the USCG but they had to scuttle their boat, Rebel Heart. Somehow, after reading that article, my only thought was: You can go see the world on your own sailboat??! We should do that!
Prior to 2014, Charlene and I were landlubbers working regular 9-5 tech jobs. We loved the outdoors and skiing was our jam (we have visited over 40 resorts together across three continents, and I have visited ten more). We also love traveling, though mostly to ski resorts. I had never gone sailing and my only leisure boating I had known was on cruise ships and a fishing trip for my cousin's bachelor party where I got seasick.
I didn't tell Charlene about this article. Instead I excitedly told her that we should take advantage of living in San Francisco and learn how to sail. She bought a Groupon at a sailing school in Oakland Estuary that same year. My memory of that first sail was a bit hazy, but I don't think it was a real sailing school, and I remember about 30 minutes into the lesson, we had to turn around as a container ship was coming down the channel and stealing all the wind (apparently the sailboat we were on didn't have an engine).
We did a bit better in 2015. I started windsurfing on an extended business trip in Singapore, and then joined Cal Sailing Club and really learned how to sail with them. Charlene ended up learning to sail with Modern Sailing a bit later.
In 2016, Charlene booked an 11 day charter in the Aegean Sea on a 50 foot monohull and we ended up loving the cruising life, especially island hopping the Dodecanese.
That trip was the point of no return. The goal was set: become capable, get a boat, and finally go see that world for ourselves. Little did we know just how much 'Paradisean' life was waiting for us.
