We met Greg in 2022, and he came with one goal in his mind – to learn how to sail his new sailboat The Red Witch, who was already waiting for him in Italy. It’s not unusual, to get the boat before the actual knowledge, and he made the right decision to take actual courses, instead of “figuring it out on the go”. Greg took with us RYA Day Skipper Theory Online, and came to Antigua to take RYA Competent Crew and RYA Day Skipper courses.
In 2020, deep into a lockdown at home in Montreal, jobless, single, living alone, and landlocked, I made the decision that I would buy a sailboat and adopt a nomadic lifestyle so I could feel free again. This may sound reactionary, and it is, but the truth is I had always held dreams of being a sailor. As long as I could remember, I had an interest in all things nautical, and I have always felt a deep spiritual connection to the water. I began to tell my friends and family of my plans. There were many questions, much disbelief, a fair bit of nay-saying, but also some support from those who knew that when I have my heart set on something I will absolutely not give it up without at least a solid shot.
‘But Greg, you don’t know anything about boats. You don’t even know how to sail!’
This may have been true then but is only slightly true now.
Later that year I found myself in Sicily looking at boats when I came across an ad on a seller’s listing site for a 1972 Alpa 11.50 near Rome called ‘The Red Witch’. I mean how cool is that, right? Aside from the name, the boat’s characteristics checked all the boxes in terms of what my needs were and the moment I stepped onboard I knew it was right. Such a beauty and such character. I pulled the trigger.



Now I just needed to learn to sail. No big deal, right? Well, sort of. My goal was to achieve Day Skipper qualification in the RYA system, something that I hoped would give me the tools to eventually sail solo. I came across Second Star Sailing and registered to do my training through the base in Antigua and I am so glad that I made this decision. The experience was phenomenal, in a truly beautiful environment, and handled by excellent instructors to whom I will forever be indebted for providing me the keys to this lifestyle. I also met some wonderful people who I still call friends today and with whom I have shared many subsequent adventures at sea. It was really hard work studying for the course after having not taken any kind of schooling in about 20 years, but I am glad I felt that pressure as it forced me to really apply myself which has paid off. I really think that anybody can do this, they just need to want it enough.


Being a boat owner isn’t easy, it isn’t always fun, but it is always interesting. It was a very memorable first outing where I thought I was having a steerage issue (my friend had inadvertently locked the helm) leading to my other friend assisting below deck turning off the engine switch with his behind while shimmying out of the quarter berth. Losing power in the mouth of a busy port is a bit stressful. It also provided a lesson. There have been so many since. When you fix something on board and the next breaks at that exact moment it can be very frustrating. On the other hand, when you make landfall in Corsica on your birthday after having crossed the Tyrrhenian Sea, escorted by an enormous pod of dolphins during one of the most beautiful sunsets you’ve ever witnessed, these problems seem so much smaller. The magic the sea can provide is truly unparalleled, and the freedom it can bring is everything that I thought it might be. Ok. Now back to the head to fix this plumbing issue.
Cheers,
Greg McEvoy