In the 90-plus charter weeks I’ve skippered, the many transfer trips, and essentially every single time I’ve stepped onto a yacht, something changes the moment we leave port. The second we cast off—every departure, without exception.
Just moments before, we’re packing things away, making final checks, immersed in the hubbub of the harbour. Then the ropes are carefully retrieved (and not fed to the propeller(s) as we move away from the dock!), and suddenly we’re free. It’s just us on board, the water holding us up, and the open space of nature and headlands. A new voyage has begun—for everyone, without exception. Even for me, and even if I’ve sailed this route thirty or forty times before.
Everyone on board has chosen to be there. They want something from it. Maybe it’s the chance to connect with loved ones—my mind goes straight to a dear mother of two grown-up sons who, for one glorious week, has them willingly “trapped” with her so she can be closer to them. No names, I promise.
Or perhaps it’s the recognition that by stripping away our usual surroundings and replacing them with something exotic, constantly changing, and sometimes even dangerous, we create a new way of relating—to others, to the group, and to ourselves. A disconnection so we can connect in a more satisfying way. A shift in mode.
Suddenly, we have a medium that allows us to reach places that would otherwise be far harder to access—and many different places in just one week. And what’s more, we have everything we need with us on board. So convenient!
Yachting holidays are surely about this enchantment of the sea and what it gives us. As a captain, I have a very deep relationship with the sea—and no, I don’t mean where we might end up in her depths. I mean profound respect. She is a jealous lover. Fail to read her mood or respect her power, and she will let you know. But read her well, respect her, and she will bless and charm you—and those you carry with you. She tests us. Pass the test, and she will woo you.
The sea is mysterious and beautiful, calming and awe-inspiring all at once if she so pleases and where she pleases. I’ve spent countless hours studying her relationship with the wind, the patterns that emerge between them, and how the yachts I sail respond best—or when it’s wiser not to go out at all.
And so, in this space of respect and devotion to the sea, we experience a freedom like no other when we cast off. Freedom to see, to do, to experience beauty, calm, power, love, laughter, and togetherness. And yes, the land too—because we experience it uniquely from the sea’s point of view. We access the meeting point of land and sea far better from the water than from the shore.
Add to that a well-maintained yacht, a good crew, wonderful local hospitality, great food and wine—and yes, incredibly fresh fish—and you simply let these powerful influences blend together and run their course, like there’s a great artist blending these experiences – the various colours – and applying them masterfully to the canvas. Or maybe the analogy is better that these elements have a life of their own and paint themselves on the canvas of this journey – they know how to forge together, weave and mix to create the masterpiece of combined experiences and a critical matter that has been reached.
I’ve seen what happens, time and time again. People open up. They relax. Their burdens are gently displaced by this convergence of beautiful things. They forget to check their emails. One Austrian client once told me he hadn’t opened his mail for three days—something he’d never done before—and he found it deeply liberating. We sat and talked about life, politics, love, wherever our thoughts wandered. He had so much to say, all delivered with great humour and insight I may add. My privilege is that I gain so much insight and wisdom from these people who are relaxing and their souls are breathing. Mine is breathing too. My summers are great “resets” for me personally. (There is a blog coming on crew-client relationships I must add!)
People open up to each other. They discover new places, feel the sea charm their socks off, and in the process discover themselves and their relationships—safe and far removed from parts of the world that don’t always understand them.
There is just so much freedom and beauty around. Do I jump off the back of the yacht into crystal-clear water for the ninth time today, or dry off in the warm sun? Pour a drink? Chat with my partner, who’s in just as good a mood as I am? Shall we arrive in port at five or six, and let the captain book a table at a taverna he knows? You go with the flow. You breathe the fresh sea air.
Then the wind comes. It’s sailing time. The engines go off and you glide along, letting the wind pass through you, almost cleansing you. You watch the sun turn the sky red, feel the sails fill, hear the wind slide over the yacht in a way that just sounds right and it matches with the sound of the water passing around and under the hull. You feel its force carry you forward and you relax in its power.
Within two days, everyone falls into the same rhythm. I often tell guests it takes me a day or two to read the group and find their ideal combined pace—and then we hit it. Together. As if we’re all sliding down the same slide at the same angle. It flows effortlessly: sailing, swimming, relaxing, laughing, eating, and fooling around.
I’ve gone on too long. But the point is this: you escape, and yet you find yourself. You rediscover connection, possibility, and what life can feel like.
And this is true even in bad weather. I’ve experienced plenty of it—bad weather, anchors dragging at night, or squals coming on so suddenly, or ropes get caught around the propellor, or anchor winches break on me and we have 80m of chain out and no motor to get it up and the guests want to go to shore and eat, or the exhaust vent which carries cooling water is also leaking into the boat and you have to bail it out – it’s all happened to me. These moments don’t ruin the experience; they deepen it. Problems get solved—often faster than you expect—or at least solved enough to adapt. That adaptation brings a little drama, some hard work, a shared laugh afterwards, and a closeness that wasn’t there before.
I feel like I’m still only at the introduction of what a yachting holiday truly offers.
