THE JOURNEY
FROM DREAM TO OPEN WATER
The Story Behind Sailing Hobo
My sailing journey was never born from a perfect plan. It began with a simple idea — that there had to be more to life than following the same road everyone else was taking.
After years of dreaming about the sea, I finally made the decision to change everything. I sold up, bought HOBO, a 1987 Moody 376, and set off to discover what life under sail was really about.
What followed wasn’t always easy, and it certainly wasn’t always to plan. There have been incredible places, rough seas, breakdowns, mistakes, friendships and more than a few unexpected adventures. But that is exactly what Sailing Hobo is about — real sailing, real stories and real freedom.
From Dream to Reality
There comes a point when dreaming about a different life is no longer enough. For me, that meant making a decision that would change everything.
I sold my house, let go of most of what i owned and started looking for a sailboat that could take me somewhere new.
That search eventually led me to HOBO, a Moody 376. She wasn’t a shiny new yacht or part of some perfect plan. She was a boat with character, capable of taking me across seas and into the life i spent years imagining.
Buying HOBO was the moment the dream became real, I wasn’t just talking about adventure anymore. I had a boat – and absolutely no idea where the journey was going to take me.
The Adventure Begins
Owning HOBO and knowing how to sail her were two very different things. Suddenly the dream had become real , and there was a lot to learn.
The early days were a mixture of excitement, mistakes, repairs and figuring things out as I went along. Some days everything worked. Other days the boat had completely different ideas.
But slowly the nautical miles began to build, confidence grew and HOBO became more than just a boat. She became home – and the adventure i had spent years imagining had finally begun
The Journey Continues
The story of SAILING HOBO is still being written. There are more seas to cross, more places to discover and, no doubt, a few more things that will break along the way.
That is what this sailing journey is really about — not perfect sailing or pretending to have all the answers, but getting out there, learning as I go and seeing where the wind takes me next.
My sailing journey is far from finished. Every passage brings something different — new coastlines, changing weather, problems to solve and lessons that can only really be learned by being out there.
HOBO has already carried me through the Greek islands, across the Mediterranean and along the coast of Spain. There have been beautiful anchorages and unforgettable days at sea, but there have also been breakdowns, repairs, rough weather and plenty of moments when the original plan went straight out the window.
That is the side of sailing I want Sailing Hobo to show. Not a polished version where everything goes perfectly, but what life aboard a cruising yacht is actually like.
There are still plenty of miles ahead. New destinations, longer passages and new adventures are waiting, and I will keep sharing the successes, the mistakes and everything I learn along the way.
The sailing journey continues one passage at a time. There is always another harbour to discover, another problem to solve and another lesson waiting beyond the horizon. Wherever HOBO takes me next, I’ll keep sharing the reality of the journey — the preparation, the mistakes, the people, the places and the freedom that keeps pulling me back to the sea.
