It All Started With a Yacht I Fell in Love With…

From Stewardess to yacht crew recruitment founder | By Cara Lees

My career in yachting began in May 1986 with a telephone call from my Dad, a rather spontaneous flight to the Caribbean and absolutely no idea where it would all lead. Decades later, having worked as a Stewardess, Cook and Purser before moving into yacht crew recruitment, I can see how those experiences shaped the agency I eventually founded.

At a glance

• Began: May 1986, aged 17, Stewardess/Deckhand on a 68ft sailing yacht
• Worked as: Stewardess, Cook, Placement Consultant, Purser on a 75m yacht
• Founded: Cara Lees Yacht Crew, 2021, Edinburgh

It all started with a phone call…

In May 1986, I was 17, living in Edinburgh and attending college, where I was studying a secretarial course.

I had absolutely no idea that one telephone call was about to change the direction of my life.

My Dad, who was running a 68ft sailing yacht with his partner, called to ask whether I had any plans for the summer. As it happened, I didn’t.

He then suggested I fly out to St Thomas in the Caribbean to join them as Stewardess/Deckhand. The plan was to sail from St Thomas to New York City via Bermuda, with a busy programme of lunches, dinners, cocktail parties up and down the Hudson and longer charters along the way.

Well, it didn’t take much persuading! Within days, I’d packed my bags, boarded a flight to St Thomas and embarked on what would become the beginning of a lifelong career in yachting. Not quite what I’d envisaged when I enrolled on my secretarial course in Edinburgh!

That first summer was a wonderful introduction to life at sea. I was learning everything from looking after guests and helping with service (I couldn’t even set a table properly in the beginning!) to getting involved on deck, all while sailing through some extraordinary places.

Our travels took us to New York and New England, including Nantucket, where I spotted a yacht that would become my next great ambition. She was a newly launched, 43m Italian-designed motor yacht, sleek, futuristic and absolutely enormous to my inexperienced eyes. I was completely captivated.

I remember thinking to myself, “I’m going to work on that yacht one day.” Little did I know that, just a few months later, I would be doing exactly that.

As the sailboat’s summer season came to an end in October of that year, I travelled from New England to Fort Lauderdale, the winter hub for yachting, in search of my next adventure. There, I became friendly with crew from that very vessel and discovered they needed a Stewardess. I approached the Captain with my CV, a fair amount of nerves and precious little experience. Then I kept going back, a couple of times a week, to remind him I was still available and very keen!

With an Atlantic crossing and Mediterranean season ahead, I desperately wanted the opportunity. Just before Christmas I was offered some daywork onboard, which then was followed by a permanent Stewardess position. I was elated. And rather proud of myself, too.

Another yacht, another ambition

I spent almost a year onboard, learning more than I could ever have imagined. At the Monaco Grand Prix, while we were berthed on the T-Quay at Quai de la Piscine, I spotted another extraordinary yacht. I thought the crew aboard must be practically superhuman to have secured positions there.

The following summer, remarkably, I joined that very yacht. It turned out to be a useful lesson in being careful what you wish for!

She was a busy charter yacht, which I loved, but the hours were eye-opening. There were three of us in the interior and the rotas weren’t always particularly fair. Much of the equipment was domestic rather than commercial, which made delivering the hotel services challenging.

It taught me early on that an impressive yacht and a glamorous itinerary don’t necessarily mean a happy or well-run working environment. How people are managed and treated matters every bit as much.

Friendships that outlast the seasons

One of the best things about yachting is the friendships. The Chef on that charter yacht was a fellow Scot, as was the Chef on my first motor yacht. We’re all still great friends. Almost four decades later, the three of us regularly meet for lunch, a laugh and a trip down memory lane. There is never a shortage of stories!

Those friendships are a reminder that, long after the season ends, it’s often the people you remember most.

A change of direction: into the galley

After a couple of years as a Stewardess, I wanted to broaden my experience. I took a cookery course and found a job as Cook on a smaller yacht.

In my experience, the galley is probably one of the most stressful places onboard. There’s constant pressure to produce excellent food, often in a confined space, against tight schedules and changing demands. It certainly taught me organisation, adaptability and respect for what every department contributes.

A family adventure, afloat and ashore

By then I’d met my future husband, who was also a yachtie. We were offered the opportunity to run a 50ft private sailing yacht together and spent a season doing just that. Then I became pregnant with our first child, and it was time to step ashore and start another adventure.

Life eventually took us to Mallorca. Although I wasn’t working onboard, yachting remained very much part of our world.

The recruitment agents I thought were gods

As a young crew member, I’d regarded yacht crew agents as almost godlike figures. After all, they could change your life with a placement, sometimes onto a wonderful yacht and sometimes, shall we say, somewhere less wonderful! I’d long fancied the idea of becoming one myself.

Just before my youngest child started school, I spotted an advert in the local newspaper for an assistant at a yacht crew agency practically on my doorstep. I applied, got the job and loved it, and my boss. Over three years, I progressed from assistant to Placement Consultant, learning the business from the ground up.

An offer too good to refuse

Then my husband was offered the Captain’s position aboard a 75m private yacht, and I was offered the Purser role. Leaving the agency was a difficult decision because I genuinely loved my job. But the salary and terms were too good to refuse, and the arrangement worked beautifully for our family.

The yacht was based in Palma during winter, giving us something approaching a normal family life. In summer, I could work remotely from home, which fitted around the children and their long school holidays. It was an unusual opportunity to combine a career at sea with family life, and one I was grateful to have.

The unexpected beginning of CLYC

After that chapter, I returned to recruitment. In March 2021, a new role with another agency ended after only a few days. It was a shock, but it also made me take stock. After more than 30 years in yachting and recruitment, I had experience, relationships and a clear idea of how I wanted to treat people. At 53, I decided to establish Cara Lees Yacht Crew.

There were doubts, lessons and plenty of coffee along the way. But the setback I hadn’t asked for became the push I needed to build a business around personal service, honest communication and placements intended to last.

Working with owners and Captains

The questions I ask

I don’t go into every conversation with a set list of questions. They tend to flow naturally, but having worked as a Stewardess, Cook and Purser helps me know what to listen for and what might need a little more exploring. I can picture the day-to-day realities behind the brief, which often leads to a more useful conversation about what the yacht needs and what will work for the crew member.

What a CV doesn’t show

Attitude, demeanour and personal presentation. A CV tells you about someone’s experience and qualifications, but not always how they communicate, carry themselves or might fit into a team. That’s why I believe a video call is essential when it isn’t possible to meet in person; those qualities often come through much better in conversation.

Making a placement last

For a placement to last, the role needs to work for both the client and the crew member. That means looking beyond salary to the itinerary, the culture on board and whether expectations on both sides are aligned. This is especially important for Heads of Department, who have a significant influence on the team and day-to-day life on board.

Some things never change

Yachts have grown, technology has transformed the industry and recruitment looks very different from when I first walked up that passerelle in Fort Lauderdale. But enthusiasm, work ethic, respect and the ability to get along with people matter just as much today.

Having worked in the interior, galley, yacht operations and recruitment, I know that the right match is about much more than a CV or the size of a yacht. It’s about the people, the working environment, and finding crew who will thrive and stay, particularly in leadership and Head of Department roles.

And sometimes, all someone needs is a Captain willing to give them a chance.

I’m certainly glad mine did.

Looking for a recruitment partner who understands life onboard firsthand? Explore Cara Lees Yacht Crew’s recruitment services or get in touch.

Prefer to speak directly? Call +44 7480 400115, email info@caraleesyachtcrew.com or WhatsApp Cara.