Professional Skipper: 8 Lessons Learned

I thought I would be in the Caribbean for a week. I stayed there four months, where I did a dozen charters as a skipper. Here are eight lessons learned from the experience.

1. A Professionnal License Helps A Lot

The service offer happens on the docks… and it happens fast! Here is an interview summary:

• Do you need a skipper in the next few weeks?
• I need them as early as next week. We’re looking for a Capitaine 200 license.
• I have a RYA YachtMaster Offshore. I’ll have the commercial endorsement and the Master of Yachts 200 gt in a few weeks.
• The YachtMaster is good. We take them.

I was then forwarded an email discussing rates and given three weeks of charter, spread over six weeks (and more thereafter).

The “interview” above is very real and is a perfect example of two essential ideas for accessing this type of work.

First, professional credentials are required. I have had exchanges about other skipper certifications, most notably the Sail Canada leisure certifications, and each time I have been told that they are looking for Capitaine 200s or RYA YachtMasters. A few exchanges with other skippers suggest that the Capitaine 200 is only of value in the French Caribbeans (Martinique, St-Martin, Guadeloupe, etc.). Elsewhere, companies seem to be asking for either the YachtMaster Offshore , the “Master Limited”, or a local certificate. I do not claim that having a professional license is an absolute, but it is certainly an asset.

Second, things happen on the docks. Your qualifications are checked afterwards, but the management teams are focused on preparing the next rentals. So you need to be on the spot, flexible… and ready to take the plunge.

2. You Must Handle the Boat, its Systems … and the Clients

My first objective was to learn how to handle different types of boats, in particular to assess which boating techniques perform well with several boats. I was quickly rewarded, working on Bali, Lagoon, Dufour and Fountaine Pajot boats ranging in length from 40 feet to 52 feet. I achieved this goal, to the point where all the boats ended up looking the same.

In retrospect, I learned much more about other dimensions of cruising than I did about boat handling. In particular, I learned a lot more about managing the diversity of crews and onboard systems.

Each charter comes with a different boat. Even boats of the same make have different configurations, depending on the year, the buyer’s configuration… and the dock staff’s repairs.

For the skipper, pre-departure inspections lasts between three and five hours, depending on how the dock personnel must rush the preparation. This is wha is availlable to understand the boat’s specifics before the customers arrive: circuit breakers, watermaker, winch, water system junctions, plumbing and through-hulls. Other secondary systems – but important to customers – such as the stereo or the fridge, must also be understood. Each of these components can turn into a potential problem once at sea, especially if you have little knowledge of how they work.

At sea, I had to understand an engine electronic injection system, diagnose which fuse was burnt out and replace it for a successful restart. I had to identify, during an anchoring manoeuver, where the windlass circuit breaker was located (obviously a different place than in the manufacturer’s manual!). I had to identify the bypass valve from the tanks to the drinking water supply pump. I had to learn how to bypass a watermaker’s automatic pressure regulation system and regulate it manually.

I have had to dismantle and reassemble a winch, climb the mast to unhook a halyard or unhook a jammed slider, disconnect an electrical socket from the main circuit to avoid a general blackout… the list goes on.

With a little experience, these tasks become commonplace… even on different boats. I quickly learned to generalize my understanding of different electrical, plumbing and mechanical systems… while at the same time learning to recognize when dockside personnel have made modifications that differ from what is indicated on the on-board plan.

I also learned how to deal with crew diversity. I faced the company manager, used to make decisions in all circumstances, and who tries to give sailing instructions despite his obvious incompetence. I faced people with difficulties conceptualizing a procedural list, and were therefore unable to carry out a manoeuver unaccompanied. I faced alcoholics who wanted to pilot the boat, the mother who was constantly worried for her children, or the “party” teenagers who threw their booze back on deck after two hours at sea.

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I had to deal with twelve people asking questions at the same time, during critical docking manoeuvers. I had to deal with people who claimed to be competent under sail and who, with every move, showed they were breaking the boat. I also had competent people onboard, but with radically different procedures for docking and mooring. I was someimes treated like a mentor, sometimes like an employee, sometimes like a friend and often like a tour guide.

I will come back to customer sociability below, but what I want to emphasize is how much it challenges and destabilizes your conceptions of manoeuvers. I had to be a constant educator, constantly checking the customers’ ability to perform a manoeuver, and ultimately, know how to regain control when things got out of hand.

A non-confrontational approach is to ask how a person usually does a manoeuver (e.g. “How do you usually hoist the mainsail?”). This allowed me to learn about different practices (I can learn too!), but above all, to identify the extent to which the customer is a risk of breaking things. In my experience, the biggest differences are in docking methods and what constitutes a “safe knot”. When the methods proposed are different from your own, and have a modicum of common sense, you need to know how to adapt. Think of any recommended order of deployment of mooring lines during docking: I have had to deal with every possible case.

It is also important to keep an eye on whether people are paying attention to the manoeuvres. Some people just phase out, leave their station to do something else, or freeze out of inexperience.

This is fine. It is not their job. It is yours.

The key message is that you need to be very flexible in the way you manage your boat, including the ways in which you find it more difficult. It is up to you to adapt to what works with your customers. Simply put, the best method is the one that works with the people on board, as opposed to a pre-established procedure. This means identifying the strengths and weaknesses of the people on board, and adapting maneuvers accordingly.

3. You Will Be Sleeping in Other People’s Berth

The charter company I worked with graciously offered me to stay on the non-chartered boats between my weeks at sea. I did not have to pay for accommodation, which was a tremendous saving. However, this benefit varies with the weeks and rental needs. One week, I had an immaculate berth on a new boat, but following, I was on a worn-out boat, with a fridge that did not work and toilets that had not yet been cleaned from the previous trip. I had to clean up and get organized!

For me, the most difficult part was certainly when the dock staff were sometimes servicing the yacht’s while I was living aboard. Important zoom meeting? Its best to do it elsewhere, or schedule it after the dock staff shifts. Others may find it difficult to have to change boats in the middle of the week, resetting the cleaning/housekeeping/temporary office setup. You have to adapt.

On the bright side, having the boat for yourself gives you a week to inspect it from top to bottom. But do not get your hopes up: it is not allowed to take it out if it is not rented!

4. You Have to Be A Tourisic Guide

Most customers expect you to have knowledge of good anchorages, good moorings and trendy restaurants. Some customers will want a tour of the best cultural sites, others will want the “best winds” for windsurfing, and some will want anchorages that do not roll. You will also be asked basic questions about demographics, culture, economics and history. “In what year was Fort XX built?”, “How many people live on the island YYY?”” and so on. You will also be asked some basic navigation questions. Is this a day when customers will be seasick? How long before we arrive? Why don’t we go in a straight line [against the wind]?

It pays to read a cruising guide and a backpacker’s guide for good restaurants. It is normal not to have an answer for everything, but pleading ignorance all the time will eventually get noticed.

You also have to put yourself in your customers’ shoes: they have flown in, paid between $6,000 and $12,000 for a week of sailing, and want to visit lots of places. Telling them that the wind is not there does not fit in with their week. You may have to use the engines and accommodate their needs.

That might mean changing course at sunset to give a nice view, slowing down to minimize discomfort during meals, cracking a few jokes to ease seasickness, organizing the recovery of suitcases lost during a flight, and doing the famous “all other related tasks”. It is their vacation.

5. You Will Be on a Catamaran More Often than on a Sailboat

The customers of charter companies can be split in two groups: those who want to sail and those who want to cruise. In the first case, customers are usually experienced, have some form of sailing certificates, prefer keelboats and do not need you at all.

In the second case, customers want a condominium on a hull, live in comfort, have little sailing experience and generally do not want to be bothered with the practicalities of sailing. So you will be on a catamaran much more often than on a keelboat: stability, space, comfort, but less performance upwind, or even under sail at all.

6. Clients From Hell

Sometimes, it is the kids who throw up, cry, push all the buttons and turn everything upside down. Sometimes, it is the adults who will treat you like their employee regardless of basic safety considerations. Other times, it will be the fanatic who talks incessantly about his religious belief, his conspiracy, or the best Star Trek episode rating. Eventually, facing some assholed becomes inevitable.

They are well represented everywhere, regardless of race, nationality, gender or religion.

I have had to argue with customers who did not understand why it was not a good idea to beach a 10-ton catamaran. I have had to make others understand that it is not a good idea to anchor between corals “even if there’s room [in a direction perpendicular to the wind]”. I’ve also had to explain the need to tuck in the mainsail before/during a gybe, even though the customer was convinced it made no difference (“You obviously haven’t learned to sail”, I was told, only to have him call the charter manager…).

This kind of customer is a ticking time bomb for a breakage. Part of the job is to prevent them despite the client’s wishes. It helps to do it tactfully and diplomatically, if time allows. When the week is over, you will have a thankfull management and maintenance team. Ultimately, some clients may even end up on the company’s “black list”.

Then come the ideologues. Whatever your convictions or ideas are on a subject, you are bound to come across people who firmly believe the opposite… and who will try to convince you. I have personally had to talk about our saviour Jesus Christ, the ineffectiveness of covid vaccines (and the pharmaceutical conspiracy to force us to take them), the fact that the earth is flat and the importance of fascism in restoring world order. This can last for seven to twenty days. As Woody Allen wrote, “Eternity is awful long time, especially towards the end”.

Finally, there are those for whom everything is due. The boat breaks down? Change everything and have a new boat delivered! Your sailing plan does not suit their whims? You need a new skipper! Food lukewarm? Change the hostess! The slightest pretext becomes an excuse to ask for a credit, complain or justify some form of superiority as a customer.

Do not get me wrong, it is normal for customers to expect a certain level of service, but I am talking here about those who are well beyond the line of decency, or who clearly do not understand what a boat cruise is all about. Here, it is very useful to remind customers that you’re in charge of operations rather than sales. The only flaw in this approach is that it shovels the problem to he administrative staff. At least, it gives customers time to calm down before returning. Perhaps a few minutes spent with the dolphins will help them forget their misfortunes!

There are no magic techniques for dealing with assholes. Minimizing interactions, let the staff on the ground know what is coming, (try to) change the subject … and count the days. You have to keep your cool, discipline yourself and remember that there are also extraordinary, generous customers who will be amazed by everything they see. Ultimately, we can also remember that we are paid to sail. If we have to pay the “tax” by doing it from time to time with social misfits, it is still worth it!

7. Equipment Breaks or Will Break

The dock staff is extremely competent. They are passionate about sailing and collectively know the boats better than the skippers. But as competent as they are, they only have seven hours to put a set of boats back in order between the arrival of the previous rentals and the start of the next ones. All in all, turnover is high, and there is very little time to go through the systems, detect problems, and fix them.

So it is also inevitable that little problems remain, due to lack of time, and that some things break at sea. This affects the customer experience, but it also affects operations as a Skipper.

Some breakdowns, such as a faulty on-board computer or autopilot, will have little effect on the customer experience, but will certainly enhance your ability to navigate with reduced functionality. Others, such as an engine failure in the middle of an anchoring procedure, will make you break out in a cold sweat!

The breakdowns that most affect the customer experience are generally related to onboard systems. The most temperamental system is undoubtedly the watermaker. In the event of a breakdown, plans have to be changed either to moderate water consumption, or to make stops to refill tanks. Some customers insist on their daily ten-minute shower (!). Fridges are also difficult, especially some drawer-sized models. This can mean a day cooking meat because the freezers are lacking.

The central idea to deprogram is that boats are in perfect working order. Some equipment will break, and navigation will have to be adapted to the state of the equipment.

8. You Will Meet Exraordinary People

People in the marine world are generally extraordinary. Sometimes you will come across a neighboring boat that is just in from a transatlantic race and is celebrating next to yours, sometimes you’ll meet customers who are discovering the wonders of sailing, sometimes another skipper will tell you his crazy stories, or sometimes you will meet company staff who are funny, competent and good-humored. These people will have an influence on the way you think about sailing, and are certainly part of the best part of the job.

Conclusion

During an evening ashore, I met a Dutch skipper who aspired to become a better sailor by sailing alone. His quest, he summed up, was to become as harmonious as possible with his boat. I explained to him how my weeks went, and he was disgusted to see me sailing with such inexperienced people. I certainly understand the perspective he is putting forward, in the sense that a professional responsibility means constantly balancing customers’ abilities, desires and safety considerations. I also aspire to be one with Jean-du-Sud, so I understand his ambitions.

That said, I counter-argued that there is a lot you can learn in a sailboat charter company that you cannot learn in a quest to harmonize with your boat. The most important learning, in my opinion, is the development of robust skills that work on several types of vessel. Conversely, the quest for harmonization leads to a form of specialization. The second learning curve is the development of the ability to make the most of any kind of crew.

Also, I sailed on incredible boats.