I should say at the outset that it was not my idea. It was my COO’s, and when she first proposed it I thought she had lost her mind. We had a leadership team of seven. We were eighteen months into a growth phase that had doubled headcount and tripled complexity. We needed a strategic offsite to align on priorities for the next fiscal year, and she suggested we do it on a yacht in the south of France.
I said no. I said we needed a conference room, a projector, a whiteboard and two days of focused work. She said we had done that for the past four years and the strategic plans we produced had lasted, on average, about six weeks before the daily chaos reasserted itself. She said the problem was not that we lacked a plan but that we lacked the conditions in which a genuinely honest conversation could happen. She said a hotel conference room was just the office with nicer carpet, and that if we wanted different thinking we needed a different environment.
I said yes, eventually, because she was right about the six weeks, and because I was tired enough to try something that made no obvious sense.
Day One: The Resistance
We boarded in Antibes on a Monday morning. The yacht was a 28-metre motor yacht with a crew of five - captain, chef, engineer, two stewards. The saloon had a table large enough for seven people to sit around comfortably, which was, in theory, our meeting room. There was no projector. There was no whiteboard. There was a large window that looked out over the Cap d’Antibes and then, as we motored out of the harbour, over an increasingly open stretch of the Mediterranean.
My CFO had brought his laptop, two external monitors and a portable printer. He set them up on the saloon table within fifteen minutes of boarding. My head of product had printed a deck of forty-seven slides. My VP of engineering was already on a video call. The habits of the office had followed us onto the water with the efficiency of a virus.
The captain came down and told us, politely, that the internet connection was satellite-based and would support basic communications but not video conferencing. My VP of engineering looked at him as though he had announced that oxygen was limited. The captain shrugged and suggested he try the foredeck if he needed better reception. He would not find it there either, but the view would be nice.
We spent the first morning doing what we always do. We talked about revenue. We talked about pipeline. We talked about the product roadmap and the engineering backlog and the hiring plan. We talked for three hours, and at the end of it my COO looked at me and said, quietly, that we had just repeated the last quarterly business review almost word for word. She was right. We had not even noticed.
Lunch was served on the aft deck. The chef had prepared something with local fish and vegetables that was better than anything I had eaten in months, but what stopped the conversation was the setting. We had anchored in a bay I did not know the name of, somewhere between Antibes and Cannes, and the water was so clear we could see the anchor chain going down to the sandy bottom six metres below. My head of product put her phone down. My CFO closed his laptop. For the first time in three hours, nobody was presenting anything.
Day Two: The Water Helps
The captain moved us overnight to the Iles de Lerins, a pair of small islands just off Cannes. We woke to the sound of nothing. No traffic. No construction. No notifications, because the satellite internet had, according to the captain, developed a minor fault that he would look into at some point. I suspect the fault was deliberate.
My COO had suggested a structure for the week. Mornings for swimming and breakfast. Mid-mornings for one focused conversation topic. Afternoons free. Evenings for dinner, during which we would talk about whatever the day had surfaced. No slides. No decks. No action item trackers. Just conversation.
The mid-morning session on day two was supposed to be about our go-to-market strategy. It became, within twenty minutes, a conversation about trust. My VP of sales said something he had clearly been holding onto for months - that he felt the product team did not respect the sales team’s understanding of customers. My head of product responded with something she had also been holding onto - that she felt the sales team routinely overpromised features to close deals and then expected engineering to build them in impossible timescales. My VP of engineering said he felt caught between the two of them and had started telling both of them what they wanted to hear rather than what was true.
This was the conversation we had never had. Not in four years of quarterly business reviews and annual offsites and weekly leadership meetings. We had never had it because the format of those meetings does not allow it. There is always an agenda, a time constraint, a next meeting to get to, a political cost to honesty that is higher than the benefit. On a yacht, anchored in a bay with nowhere else to be and nothing else to do, the cost-benefit calculation shifts. The honesty becomes cheaper than the alternative, because the alternative - another year of the same unspoken tensions - is sitting right there at the same table, and everyone can see it.
Day Three: Moving
We sailed to Saint-Tropez. Not the town itself, which none of us had any interest in visiting, but a bay on the peninsula to the south where the coast is rocky and undeveloped and the water is a shade of blue that made my CFO, a man who considers beauty an inefficiency, put down his coffee and stare for a full minute.
The physical movement of the yacht helped in ways I did not expect. When you are walking between sessions in a hotel, you are still in an institutional space. The corridors, the lobbies, the elevators - they all reinforce the context of work. When you are moving between conversations on a yacht, you are moving through space that is beautiful and unfamiliar, and the movement itself changes the texture of your thinking. I found that my best ideas came not during the formal sessions but during the transitions - standing on the foredeck while the coastline passed, or sitting on the swim platform with my feet in the water, or watching the sunset from the flybridge with a glass of something cold.
The others reported the same thing. My head of product said she had solved a structural problem with our product architecture while swimming. My VP of engineering said he had figured out the staffing model for Q3 while watching the chef prepare dinner. My COO said the real strategic insight of the trip had come to her during a walk along the beach on the Ile Sainte-Marguerite, and that it had nothing to do with strategy and everything to do with pace.
She said we had been building the company as though speed were the only virtue. That we had optimised every process for velocity and in doing so had eliminated the space in which people think clearly, make good decisions, and maintain their health. She said the yacht was showing us what pace should feel like, and that if we could bring even a fraction of that into the way we ran the company, we would make better decisions, lose fewer people, and ultimately grow faster by going more deliberately.
Day Four: The Real Plan
On the fourth day, we built the plan. Not with slides or spreadsheets or frameworks borrowed from management consultants. With a conversation that lasted from mid-morning until late afternoon, interrupted only by lunch and swimming and the captain’s decision to move us to a quieter anchorage when the wind shifted.
The plan was simple. Simpler than any plan we had produced before. Three priorities for the year, not twelve. A commitment to protect unstructured time in the calendar for every member of the leadership team. A restructuring of the product-sales relationship that gave each side genuine decision-making authority in the areas the other had been encroaching on. And a quarterly offsite - not on a yacht, sadly, because the budget would not support it, but outside of the office, in an environment that broke the pattern of the conference room.
My CFO built a financial model on a napkin. My VP of engineering sketched an org chart on the back of a menu. My head of product wrote the product vision statement on her phone, standing on the aft deck in her swimming costume, and it was three sentences long and better than anything we had produced in a full-day workshop with a professional facilitator.
The plan stuck. I want to be clear about this, because it is the thing that surprised me most. The plan lasted the year. Not because it was a better plan - although I think it was - but because the people who made it had been through something together that changed the way they related to each other. They had been honest in a way that the office did not permit. They had seen each other swim, and cook, and laugh at the captain’s terrible jokes, and sit in silence looking at the water. They had spent five days in an environment that removed every prop and pretence of corporate life and left them with nothing except each other and the work, and the result was that the work improved because the relationships improved.
Day Five: Leaving
We docked in Antibes on the Friday morning. The CFO packed his laptop and his monitors and his portable printer, all of which he had not used since day one. My VP of engineering had not been on a video call since the satellite internet developed its convenient fault. My head of product had not opened her forty-seven-slide deck.
Standing on the quay, bags at our feet, waiting for the transfer to Nice airport, my VP of sales said something I have thought about many times since. He said that in fifteen years of corporate offsites - at hotels, at conference centres, at team-building facilities with ropes courses and trust falls and mandatory fun - this was the first one where he had actually said what he thought. Not because anyone told him to. Because the environment made it possible.
I do not think a yacht is the only environment that can do this. I think a cabin in the mountains or a house on a lake might work too. But I think the yacht has something specific that the others do not: it moves. It takes you somewhere new every day. It makes the conversation feel like a journey rather than a meeting. And the water - always the water, everywhere you look, calm and deep and endlessly blue - does something to the way people hold themselves. It loosens something. It removes the rigidity that accumulates over months and years of sitting in offices and talking in frameworks and performing confidence.
We have done it once more since, two years later, along the same coast. The plan from that trip is still intact. The team is still together. And the company is in a different place - not because of any single decision we made on the water, but because of what the water did to the people making the decisions.
This account is based on conversations with a technology company CEO who completed two leadership retreats by yacht on the French Riviera. Names and identifying details have been changed. Corporate retreat charters can be tailored to specific team sizes, objectives and working styles.